Abstract
In the context of global warming and the future circular economy, chemical fixation of carbon dioxide (CO2) is a fast-developing research area because gaseous CO2 could be trapped and converted into value-added products, industrial chemicals and pharmaceuticals. The latest advancements focus on homogeneous and heterogeneous catalysts, yet drawbacks of high price, complicated design and difficult recovery need to be circumvented. Although the catalyst-free concept has been extensively used in synthetic chemistry, this paradigm remains underexplored in the domain of CO2 conversion. Therefore, here we review catalyst-free chemical and photochemical fixation of CO2 for the manufacture of products such as ureas, carbamates, oxazolidinones, quinazoline-2,4(1H,3H)-diones, benzimidazoles, 1,6-dioxospiro/1,6-dioxaspiro derivatives, polymers, N-formamides, N-methylamines and carboxylic acids. Noteworthy, the catalyst-free conversion of CO2 can be accomplished in water or in solvent-less conditions. We also discuss the reaction mechanisms leading to the formation of CO2-derived products in the absence of any catalyst or additives.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Abbreviations
- TMS:
-
Trimethylsilyl
- TBS:
-
tert-Butyldimethylsilyl
- TBDPS:
-
tert-Butyldiphenylsilyl
- TIPS:
-
Triisopropylsilyl
- GC-FID:
-
GC with flame ionization detector
- CH3OH:
-
Methanol
- CH3CN:
-
Acetonitrile
- C2H3Cl3 :
-
1,1,1-Trichloroethane
- THF:
-
Tetrahydrofuran
- Mw:
-
Molecular weight
- DAD:
-
1,12-Diaminododecane
- EDR-104:
-
1,5-Diamino-3-oxapentane
- DMA:
-
N,N-Dimethylacetamide
- DMO:
-
Methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate
References
Al-Saydeh SA, Zaidi SJ (2018) Carbon dioxide conversion to methanol: opportunities and fundamental challenges. Carbon Dioxide Chem Capture Oil Recovery. https://doi.org/10.5772/intechopen.74779
Altuntas I, Delibas N, Doguc DK, Ozmen S, Gultekin F (2003) Role of reactive oxygen species in organophosphate insecticide phosalone toxicity in erythrocytes in vitro. Toxicol In Vitro 17(2):153–157. https://doi.org/10.1016/s0887-2333(02)00133-9
Aresta M, Dibenedetto A, Pastore C (2005) Biotechnology to develop innovative syntheses using CO2. Environ Chem Lett 3(3):113–117. https://doi.org/10.1007/s10311-005-0009-y
Arshadi S, Banaei A, Ebrahimiasl S, Monfared A, Vessally E (2019) Solvent-free incorporation of CO2 into 2-oxazolidinones: a review. RSC Adv 9(34):19465–19482. https://doi.org/10.1039/c9ra00551j
Arshadi S, Vessally E, Hosseinian A, Soleimani-amiri S, Edjlali L (2017) Three-component coupling of CO2, propargyl alcohols, and amines: an environmentally benign access to cyclic and acyclic carbamates (a review). J CO2 Util 21:108–118. https://doi.org/10.1016/j.jcou.2017.07.008
Arshadi S, Vessally E, Sobati M, Hosseinian A, Bekhradnia A (2017) Chemical fixation of CO2 to N -propargylamines: A straightforward route to 2-oxazolidinones. J CO2 Util 19:120–129. https://doi.org/10.1016/j.jcou.2017.03.009
Aue DH, Webb HM, Bowers MT (1976) A thermodynamic analysis of solvation effects on the basicities of alkylamines. an electrostatic analysis of substituent effects. J Am Chem Soc 98(2):318–329. https://doi.org/10.1021/ja00418a002
Bhanage BM, Fujita S-i, Ikushima Y, Arai M (2003) Synthesis of cyclic ureas and urethanes from alkylene diamines and amino alcohols with pressurized carbon dioxide in the absence of catalysts. Green Chem 5(3):340. https://doi.org/10.1039/b300778b
Blondiaux E, Pouessel J, Cantat T (2014) Carbon dioxide reduction to methylamines under metal-free conditions. Angew Chem Int Ed Engl 53(45):12186–12190. https://doi.org/10.1002/anie.201407357
Bobbink FD, Das S, Dyson PJ (2017) N-formylation and N-methylation of amines using metal-free N-heterocyclic carbene catalysts and CO2 as carbon source. Nat Protoc 12(2):417–428. https://doi.org/10.1038/nprot.2016.175
Brahmachari G, Banerjee B (2015) Catalyst-free organic synthesis at room temperature in aqueous and non-aqueous media: an emerging field of green chemistry practice and sustainability. Current Green Chem 2(3):274–305. https://doi.org/10.2174/2213346102666150218195142
Bresciani G, Antico E, Ciancaleoni G, Zacchini S, Pampaloni G, Marchetti F (2020) Bypassing the inertness of aziridine/CO2 systems to access 5-Aryl-2-oxazolidinones: catalyst-free synthesis under ambient conditions. Chemsuschem. https://doi.org/10.1002/cssc.202001823
Bruffaerts J, von Wolff N, Diskin-Posner Y, Ben-David Y, Milstein D (2019) Formamides as isocyanate surrogates: a mechanistically driven approach to the development of atom-efficient, selective catalytic syntheses of ureas, carbamates, and heterocycles. J Am Chem Soc 141(41):16486–16493. https://doi.org/10.1021/jacs.9b08942
Bruneau C, Dixncuf PH (1987) Catalytic synthesis of O-β-oxoalkylcarbamates. Tetrahedron Lett 28(18):2005–2008. https://doi.org/10.1016/s0040-4039(00)96031-3
Burgess SA, Kendall AJ, Tyler DR, Linehan JC, Appel AM (2017) Hydrogenation of CO2 in water using a bis(diphosphine) Ni–H complex. ACS Catal 7(4):3089–3096. https://doi.org/10.1021/acscatal.7b00350
Considine GD (2005) Van Nostrand's scientific encyclopedia. In: Formamide. Wiley, Hoboken. https://doi.org/10.1002/0471743984.vse8054
Chanda A, Fokin VV (2009) Organic synthesis “on water.” Chem Rev 109(2):725–748. https://doi.org/10.1021/cr800448q
Chang L, Zhiani R, Sadeghzadeh SM (2019) Fixing CO2 into β-oxopropylcarbamates in neat condition by ionic gelation/Ag(i) supported on dendritic fibrous nanosilica. RSC Advances 9(30):16955–16965. https://doi.org/10.1039/c9ra02680k
Chaturvedi D, Chaturvedi AK, Mishra V (2012) Carbon dioxide: versatile, cheap and safe alternative in the syntheses of organic carbamates. Current Org Chem 16(13):1609–1635. https://doi.org/10.2174/138527212800840982
Chen Y, Mu T (2019) Conversion of CO2 to value-added products mediated by ionic liquids. Green Chem 21(10):2544–2574. https://doi.org/10.1039/c9gc00827f
Cheng R, Qi C, Wang L, Xiong W, Liu H, Jiang H (2020) Visible light-promoted synthesis of organic carbamates from carbon dioxide under catalyst- and additive-free conditions. Green Chem 22(15):4890–4895. https://doi.org/10.1039/d0gc00910e
Cioc RC, Ruijter E, Orru RVA (2014) Multicomponent reactions: advanced tools for sustainable organic synthesis. Green Chem 16(6):2958–2975. https://doi.org/10.1039/c4gc00013g
Coma M, Martinez-Hernandez E, Abeln F, Raikova S, Donnelly J, Arnot TC, Allen MJ, Hong DD, Chuck CJ (2017) Organic waste as a sustainable feedstock for platform chemicals. Faraday Discuss 202:175–195. https://doi.org/10.1039/c7fd00070g
Coufourier S, Gaignard Gaillard Q, Lohier J-F, Poater A, Gaillard S, Renaud J-L (2020) Hydrogenation of CO2, hydrogenocarbonate, and carbonate to formate in water using phosphine free bifunctional iron complexes. ACS Catal 10(3):2108–2116. https://doi.org/10.1021/acscatal.9b04340
Cravotto G, Cintas P (2006) Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem Soc Rev 35(2):180–196. https://doi.org/10.1039/b503848k
Cui X, Zhang Y, Deng Y, Shi F (2014) Amine formylation via carbon dioxide recycling catalyzed by a simple and efficient heterogeneous palladium catalyst. Chem Commun (Camb) 50(2):189–191. https://doi.org/10.1039/c3cc46427j
Dabral S, Schaub T (2019) The use of carbon dioxide (CO2) as a building block in organic synthesis from an industrial perspective. Adv Synth Catal 361(2):223–246. https://doi.org/10.1002/adsc.201801215
Dai X, Wang B, Wang A, Shi F (2019) Amine formylation with CO2 and H2 catalyzed by heterogeneous Pd/PAL catalyst. Chin J Catal 40(8):1141–1146. https://doi.org/10.1016/s1872-2067(19)63397-8
Darensbourg DJ, Andreatta JR, Moncada AI (2010) Polymers from carbon dioxide: polycarbonates. Polythiocarbonates Polyurethanes. https://doi.org/10.1002/9783527629916.ch8
Das Neves Gomes C, Jacquet O, Villiers C, Thuery P, Ephritikhine M, Cantat T (2012) A diagonal approach to chemical recycling of carbon dioxide: organocatalytic transformation for the reductive functionalization of CO2. Angew Chem Int Ed Engl 51(1):187–190. https://doi.org/10.1002/anie.201105516
Daw P, Chakraborty S, Leitus G, Diskin-Posner Y, Ben-David Y, Milstein D (2017) Selective N-formylation of amines with H2 and CO2 catalyzed by cobalt pincer complexes. ACS Catal 7(4):2500–2504. https://doi.org/10.1021/acscatal.7b00116
Denlinger KL, Mack J (2018) Solvent-free synthesis. Green Tech Org Synth Med Chem. https://doi.org/10.1002/9781119288152.ch13
Dyen ME, Swern D (1967) 2-oxazolidones. Chem Rev 67(2):197–246. https://doi.org/10.1021/cr60246a003
Fiorani G, Guo W, Kleij AW (2015) Sustainable conversion of carbon dioxide: the advent of organocatalysis. Green Chem 17(3):1375–1389. https://doi.org/10.1039/c4gc01959h
Frogneux X, Jacquet O, Cantat T (2014) Iron-catalyzed hydrosilylation of CO2: CO2 conversion to formamides and methylamines. Catal Sci Technol 4(6):1529–1533. https://doi.org/10.1039/c4cy00130c
Fuchter MJ, Smith CJ, Tsang MW, Boyer A, Saubern S, Ryan JH, Holmes AB (2008) Clean and efficient synthesis of O-silylcarbamates and ureas in supercritical carbon dioxide. Chem Commun (Camb) 18:2152–2154. https://doi.org/10.1039/b801537f
Fujita K-i, Sato J, Inoue K, Tsuchimoto T, Yasuda H (2014) Aqueous media carboxylative cyclization of propargylic amines with CO2 catalyzed by amphiphilic dendritic N-heterocyclic carbene–gold(I) complexes. Tetrahedron Lett 55(19):3013–3016. https://doi.org/10.1016/j.tetlet.2014.03.074
Gawande MB, Bonifacio VD, Luque R, Branco PS, Varma RS (2013) Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis. Chem Soc Rev 42(12):5522–5551. https://doi.org/10.1039/c3cs60025d
Gawande MB, Bonifacio VD, Luque R, Branco PS, Varma RS (2014) Solvent-free and catalysts-free chemistry: a benign pathway to sustainability. Chemsuschem 7(1):24–44. https://doi.org/10.1002/cssc.201300485
Gawande MB, Shelke SN, Zboril R, Varma RS (2014) Microwave-assisted chemistry: synthetic applications for rapid assembly of nanomaterials and organics. Acc Chem Res 47(4):1338–1348. https://doi.org/10.1021/ar400309b
Giezendanner H, Märky M, Jackson B, Hansen HJ, Schmid H (1972) Photoinduced reactions of aryl-2H-azirines with carbonyl compounds. preliminary Commununication. Helv Chim Acta 55(3):745–748. https://doi.org/10.1002/hlca.19720550302
Glaser JA (2012) Green chemistry with nanocatalysts. Clean Technol Environ Policy 14(4):513–520. https://doi.org/10.1007/s10098-012-0507-0
Gong Z-J, Li Y-R, Wu H-L, Lin SD, Yu W-Y (2020) Direct copolymerization of carbon dioxide and 1,4-butanediol enhanced by ceria nanorod catalyst. Appl Catal B 265:118524. https://doi.org/10.1016/j.apcatb.2019.118524
González-Sebastián L, Flores-Alamo M, García JJ (2015) Selective N-Methylation of aliphatic amines with CO2 and hydrosilanes using nickel-phosphine catalysts. Organometallics 34(4):763–769. https://doi.org/10.1021/om501176u
Gopakumar A, Lombardo L, Fei Z, Shyshkanov S, Vasilyev D, Chidambaram A, Stylianou K, Züttel A, Dyson PJ (2020) A polymeric ionic liquid catalyst for the N-formylation and N-methylation of amines using CO2/PhSiH3. J CO2 Util 41:101240. https://doi.org/10.1016/j.jcou.2020.101240
Grignard B, Gennen S, Jerome C, Kleij AW, Detrembleur C (2019) Advances in the use of CO2 as a renewable feedstock for the synthesis of polymers. Chem Soc Rev 48(16):4466–4514. https://doi.org/10.1039/c9cs00047j
Guo Z, Zhang B, Wei X, Xi C (2018) 1,4-dioxane-tuned catalyst-free methylation of amines by CO2 and NaBH4. Chemsuschem 11(14):2296–2299. https://doi.org/10.1002/cssc.201801037
Hao L, Zhang H, Luo X, Wu C, Zhao Y, Liu X, Gao X, Chen Y, Liu Z (2017) Reductive formylation of amines with CO2 using sodium borohydride: a catalyst-free route. J CO2 Util 22:208–211. https://doi.org/10.1016/j.jcou.2017.10.007
Harding SL, Savage GP (2012) Facial selectivity induced by N-aryl atropisomerism in benzonitrile oxide cycloadditions with 4-methylene-2-oxazolidinones. Org Biomol Chem 10(24):4759–4766. https://doi.org/10.1039/c2ob25271f
He L-N, Dou X-Y, Yang Z-Z, Wang J-L (2010) Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide. Synlett 2010(14):2159–2163. https://doi.org/10.1055/s-0030-125851
Heravi MM, Zadsirjan V (2013) Oxazolidinones as chiral auxiliaries in asymmetric aldol reactions applied to total synthesis. Tetrahedron Asymmetry 24(19):1149–1188. https://doi.org/10.1016/j.tetasy.2013.08.011
Hoffmann N (2008) Photochemical reactions as key steps in organic synthesis. Chem Rev 108(3):1052–1103. https://doi.org/10.1021/cr0680336
Horvath IT, Anastas PT (2007) Innovations and green chemistry. Chem Rev 107(6):2169–2173. https://doi.org/10.1021/cr078380v
Hu J, Chen S, Guo Y, Li L, Deng T (2018) Basic salt-lake brine: an efficient catalyst for the transformation of CO2 into quinazoline-2,4(1 H,3 H)-diones. Chemsuschem 11(24):4219–4225. https://doi.org/10.1002/cssc.201802431
Hu YL, Zhang RL, Fang D (2018) Quaternary phosphonium cationic ionic liquid/porous metal–organic framework as an efficient catalytic system for cycloaddition of carbon dioxide into cyclic carbonates. Environ Chem Lett 17(1):501–508. https://doi.org/10.1007/s10311-018-0793-9
Huang J, Worch JC, Dove AP, Coulembier O (2020) Update and challenges in carbon dioxide-based polycarbonate synthesis. Chemsuschem 13(3):469–487. https://doi.org/10.1002/cssc.201902719
Huang K, Zhang J-Y, Liu F, Dai S (2018) Synthesis of porous polymeric catalysts for the conversion of carbon dioxide. ACS Catal 8(10):9079–9102. https://doi.org/10.1021/acscatal.8b02151
Hulla M, Bobbink FD, Das S, Dyson PJ (2016) Carbon Dioxide based N-formylation of amines catalyzed by fluoride and hydroxide anions. ChemCatChem 8(21):3338–3342. https://doi.org/10.1002/cctc.201601027
Hwang J, Han D, Oh JJ, Cheong M, Koo H-J, Lee JS, Kim HS (2019) Efficient non-catalytic carboxylation of diamines to cyclic ureas using 2-pyrrolidone as a solvent and a promoter. Adv Synth Catal 361(2):297–306. https://doi.org/10.1002/adsc.201800945
Irmak S (2017) Biomass as Raw Material for Production of High-Value Products. Biomass Vol Estim Valoriz. https://doi.org/10.5772/65507
Ishaq H, Siddiqui O, Chehade G, Dincer I (2020) A solar and wind driven energy system for hydrogen and urea production with CO2 capturing. Int J Hydrogen Energy. https://doi.org/10.1016/j.ijhydene.2020.01.208
Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T (2013) Complete catalytic deoxygenation of CO2 into formamidine derivatives. ChemCatChem 5(1):117–120. https://doi.org/10.1002/cctc.201200732
Jadhav PK, Ala P, Woerner FJ, Chang CH, Garber SS, Anton ED, Bacheler LT (1997) Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV. J Med Chem 40(2):181–191. https://doi.org/10.1021/jm960586t
Jangam A, Das S, Dewangan N, Hongmanorom P, Hui WM, Kawi S (2019) Conversion of CO2 to C1 chemicals: catalyst design, kinetics and mechanism aspects of the reactions. Catal Today. https://doi.org/10.1016/j.cattod.2019.08.049
Jia J, Qian C, Dong Y, Li YF, Wang H, Ghoussoub M, Butler KT, Walsh A, Ozin GA (2017) Heterogeneous catalytic hydrogenation of CO2 by metal oxides: defect engineering—perfecting imperfection. Chem Soc Rev 46(15):4631–4644. https://doi.org/10.1039/c7cs00026j
Jiang S, Cheng HY, Shi RH, Wu PX, Lin WW, Zhang C, Arai M, Zhao FY (2019) Direct synthesis of polyurea thermoplastics from CO2 and diamines. ACS Appl Mater Interfaces 11(50):47413–47421. https://doi.org/10.1021/acsami.9b17677
Jiang S, Shi R, Cheng H, Zhang C, Zhao F (2017) Synthesis of polyurea from 1,6-hexanediamine with CO2 through a two-step polymerization. Green Energy Environ 2(4):370–376. https://doi.org/10.1016/j.gee.2017.05.001
Jin S-J, Khan Y, Maeng JH, Kim YJ, Hwang J, Cheong M, Lee JS, Kim HS (2017) Efficient catalytic systems for the carboxylation of diamines to cyclic ureas using ethylene urea as a promoter. Appl Catal B 209:139–145. https://doi.org/10.1016/j.apcatb.2017.02.079
Kayaki Y, Yamamoto M, Suzuki T, Ikariya T (2006) Carboxylative cyclization of propargylamines with supercritical carbon dioxide. Green Chem 8(12):1019. https://doi.org/10.1039/b603700c
Kharissova OV, Kharisov BI, Oliva Gonzalez CM, Mendez YP, Lopez I (2019) Greener synthesis of chemical compounds and materials. R Soc Open Sci 6(11):191378. https://doi.org/10.1098/rsos.191378
Khatun R, Biswas S, Islam S, Biswas IH, Riyajuddin S, Ghosh K, Islam SM (2019) Modified Graphene oxide based zinc composite: an efficient catalyst for N-formylation and carbamate formation reactions through CO2 fixation. ChemCatChem 11(4):1303–1312. https://doi.org/10.1002/cctc.201801963
Kim H-S, Kim J-W, Kwon S-C, Shim S-C, Kim T-J (1997) Catalytic formation of carbamates and cyclic carbonates by copper complex of 2,5,19,22-tetraaza[6,6](1,1′)ferrocenophane-1,5-diene X-ray crystal structure of [Cu(1)]PF6. J Organomet Chem 545–546:337–344. https://doi.org/10.1016/s0022-328x(97)00366-5
Kim T-J, Kwon K-H, Kwon S-C, Baeg J-O, Shim S-C, Lee D-H (1990) Iron complexes of 1,1′-bis(diphenylphosphino)ferrocene (BPPF) as efficient catalysts in the synthesis of carbamates. X-ray crystal structure of (BPPF)Fe(CO)3. J Organom Chem 389(2):205–217. https://doi.org/10.1016/0022-328x(90)85412-r
Kindermann N, Jose T, Kleij AW (2017) Synthesis of carbonates from alcohols and CO2. Top Curr Chem (Cham) 375(1):15. https://doi.org/10.1007/s41061-016-0101-8
Kitanosono T, Kobayashi S (2020) Reactions in water involving the “on-water” mechanism. Chemistry 26(43):9408–9429. https://doi.org/10.1002/chem.201905482
Kitanosono T, Masuda K, Xu P, Kobayashi S (2018) Catalytic organic reactions in water toward sustainable society. Chem Rev 118(2):679–746. https://doi.org/10.1021/acs.chemrev.7b00417
Knopf I, Cummins CC (2015) Revisiting CO2 reduction with NaBH4 under aprotic conditions: synthesis and characterization of sodium triformatoborohydride. Organometallics 34(9):1601–1603. https://doi.org/10.1021/acs.organomet.5b00190
Kondo K, Yokoyama S, Miyoshi N, Murai S, Sonoda N (1979) Reactions of carbonyl selenide with amines and aminoalcohols to produce ureas and carbamates. Angew Chem Int Ed Engl 18(9):692–692. https://doi.org/10.1002/anie.197906921
Kozak CM, Ambrose K, Anderson TS (2018) Copolymerization of carbon dioxide and epoxides by metal coordination complexes. Coord Chem Rev 376:565–587. https://doi.org/10.1016/j.ccr.2018.08.019
Kumar S, Verma S, Shawat E, Nessim GD, Jain SL (2015) Amino-functionalized carbon nanofibres as an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles. RSC Advances 5(31):24670–24674. https://doi.org/10.1039/c5ra01900a
Kurihara M, Rouf AS, Kansui H, Kagechika H, Okuda H, Miyata N (2004) Design and synthesis of cyclic urea compounds: a pharmacological study for retinoidal activity. Bioorg Med Chem Lett 14(16):4131–4134. https://doi.org/10.1016/j.bmcl.2004.06.038
Lai MF, Li J, Liu JJ (2005) Thermal and dynamic mechanical properties of poly(propylene carbonate). J Therm Anal Calorim 82(2):293–298. https://doi.org/10.1007/s10973-005-0892-2
Lais A, Gondal MA, Dastageer MA (2017) Semiconducting oxide photocatalysts for reduction of CO2 to methanol. Environ Chem Lett 16(1):183–210. https://doi.org/10.1007/s10311-017-0673-8
Lamb KJ, Ingram IDV, North M, Sengoden M (2019) Valorization of carbon dioxide into oxazolidinones by reaction with aziridines. Current Green Chem 6(1):32–43. https://doi.org/10.2174/2213346106666190321142328
Li CJ, Chen L (2006) Organic chemistry in water. Chem Soc Rev 35(1):68–82. https://doi.org/10.1039/b507207g
Li G, Chen J, Zhu D-Y, Chen Y, Xia J-B (2018) DBU-catalyzed selective N-methylation and N-formylation of amines with CO2 and Polymethylhydrosiloxane. Adv Synth Catal 360(12):2364–2369. https://doi.org/10.1002/adsc.201800140
Li WD, Zhu DY, Li G, Chen J, Xia JB (2019) Iron-catalyzed selective N-methylation and N-formylation of amines with CO2. Adv Synth Catal 361(22):5098–5104. https://doi.org/10.1002/adsc.201900906
Liang J, Ye S, Wang S, Xiao M, Meng Y (2020) Design and structure of catalysts: syntheses of carbon dioxide-based copolymers with cyclic anhydrides and/or cyclic esters. Polym J. https://doi.org/10.1038/s41428-020-0374-1
Liu A-H, Yu B, He L-N (2015) Catalytic conversion of carbon dioxide to carboxylic acid derivatives. Greenh Gases Sci Technol 5(1):17–33. https://doi.org/10.1002/ghg.1461
Liu H, Nie Z, Shao J, Chen W, Yu Y (2019) Mild and facile synthesis of formamide: reduction and functionalization of CO2 using NaBH(OAc)3 under atmospheric pressure. Green Chem 21(13):3552–3555. https://doi.org/10.1039/c9gc01137d
Liu L, Lukose B, Ensing B (2018) A free energy landscape of CO2 capture by frustrated lewis pairs. ACS Catal 8(4):3376–3381. https://doi.org/10.1021/acscatal.7b04072
Liu M, Sun Y, Liang Y, Lin B-L (2017) Highly efficient synthesis of functionalizable polymers from a CO2/1,3-butadiene-derived lactone. ACS Macro Lett 6(12):1373–1378. https://doi.org/10.1021/acsmacrolett.7b00774
Liu Q, Wu L, Jackstell R, Beller M (2015) Using carbon dioxide as a building block in organic synthesis. Nat Commun 6:5933. https://doi.org/10.1038/ncomms6933
Liu R, Liu X, Ouyang K, Yan Q (2019) Catalyst-free click polymerization of CO2 and lewis monomers for recyclable C1 fixation and release. ACS Macro Lett 8(2):200–204. https://doi.org/10.1021/acsmacrolett.9b00066
Liu X-F, Wang M-Y, He L-N (2017) Heterogeneous catalysis for oxazolidinone synthesis from aziridines and CO2. Curr Org Chem 21(8):698–707. https://doi.org/10.2174/1385272820666161017115814
Liu Z, Yang Z, Ke Z, Yu X, Zhang H, Yu B, Zhao Y, Liu Z (2018) Ethanol-mediated N-formylation of amines with CO2/H2 over cobalt catalysts. New J Chem 42(16):13933–13937. https://doi.org/10.1039/c8nj03047b
Long Ngo H, Kumar Mishra D, Mishra V, Chien Truong C (2021) Recent advances in the synthesis of heterocycles and pharmaceuticals from the photo/electrochemical fixation of carbon dioxide. Chem Eng Sci 229:116142. https://doi.org/10.1016/j.ces.2020.116142
Lu C, Qiu Z, Zhu Y, Lin B-L (2019) Scalable direct N-methylation of drug-like amines using 12CO2/13CO2 by simple inorganic base catalysis. Sci Bull 64(11):723–729. https://doi.org/10.1016/j.scib.2019.04.032
Lu W, Ma J, Hu J, Zhang Z, Wu C, Han B (2014) Choline hydroxide promoted chemical fixation of CO2 to quinazoline-2,4(1H,3H)-diones in water. RSC Adv 4(92):50993–50997. https://doi.org/10.1039/c4ra08551e
Lu Z, Williams TJ (2016) Di(carbene)-supported nickel systems for CO2 reduction under ambient conditions. ACS Catal 6(10):6670–6673. https://doi.org/10.1021/acscatal.6b02101
Lv H, Wang W, Li F (2018) Porous organic polymers with built-in N-heterocyclic carbenes: selective and efficient heterogeneous catalyst for the reductive N-formylation of amines with CO2. Chemistry 24(62):16588–16594. https://doi.org/10.1002/chem.201803364
Lv H, Xing Q, Yue C, Lei Z, Li F (2016) Solvent-promoted catalyst-free N-formylation of amines using carbon dioxide under ambient conditions. Chem Commun (Camb) 52(39):6545–6548. https://doi.org/10.1039/c6cc01234e
Ma J, Han B, Song J, Hu J, Lu W, Yang D, Zhang Z, Jiang T, Hou M (2013) Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in water without any catalyst. Green Chem 15(6):1485. https://doi.org/10.1039/c3gc00091e
Ma J, Hu J, Lu W, Zhang Z, Han B (2013) Theoretical study on the reaction of CO2 and 2-aminobenzonitrile to form quinazoline-2,4(1H,3H)-dione in water without any catalyst. Phys Chem Chem Phys 15(40):17333–17341. https://doi.org/10.1039/c3cp52977k
Maina JW, Pozo-Gonzalo C, Kong L, Schütz J, Hill M, Dumée LF (2017) Metal organic framework based catalysts for CO2 conversion. Mater Horiz 4(3):345–361. https://doi.org/10.1039/c6mh00484a
Masuda Y, Ishida N, Murakami M (2015) Light-driven carboxylation of o-alkylphenyl ketones with CO2. J Am Chem Soc 137(44):14063–14066. https://doi.org/10.1021/jacs.5b10032
Merino O, Santoyo BM, Montiel LE, Jiménez-Vázquez HA, Zepeda LG, Tamariz J (2010) Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides. Tetrahedron Lett 51(29):3738–3742. https://doi.org/10.1016/j.tetlet.2010.05.034
Metzger JO (2009) Fats and oils as renewable feedstock for chemistry. Eur J Lipid Sci Technol 111(9):865–876. https://doi.org/10.1002/ejlt.200900130
Molla RA, Bhanja P, Ghosh K, Islam SS, Bhaumik A, Islam SM (2017) Pd nanoparticles decorated on hypercrosslinked microporous polymer: a highly efficient catalyst for the formylation of amines through carbon dioxide fixation. ChemCatChem 9(11):1939–1946. https://doi.org/10.1002/cctc.201700069
Momming CM, Otten E, Kehr G, Frohlich R, Grimme S, Stephan DW, Erker G (2009) Reversible metal-free carbon dioxide binding by frustrated Lewis pairs. Angew Chem Int Ed Engl 48(36):6643–6646. https://doi.org/10.1002/anie.200901636
Monfared A, Mohammadi R, Hosseinian A, Sarhandi S, Kheirollahi Nezhad PD (2019) Cycloaddition of atmospheric CO2 to epoxides under solvent-free conditions: a straightforward route to carbonates by green chemistry metrics. RSC Adv 9(7):3884–3899. https://doi.org/10.1039/c8ra10233c
Motokura K, Takahashi N, Kashiwame D, Yamaguchi S, Miyaji A, Baba T (2013) Copper-diphosphine complex catalysts for N-formylation of amines under 1 atm of carbon dioxide with polymethylhydrosiloxane. Catal Sci Technol 3(9):2392. https://doi.org/10.1039/c3cy00375b
Mu J, Liu J, Ran Z, Arif M, Gao M, Wang C, Ji S (2020) Critical role of CUS in the Au/MOF-808(Zr) catalyst for reaction of CO2 with amine/H2 via N-methylation and N-formylation. Ind Eng Chem Res 59(14):6543–6555. https://doi.org/10.1021/acs.iecr.0c00242
Mu ZJ, Ding X, Chen ZY, Han BH (2018) Zwitterionic covalent organic frameworks as catalysts for hierarchical reduction of CO2 with amine and hydrosilane. ACS Appl Mater Interfaces 10(48):41350–41358. https://doi.org/10.1021/acsami.8b14671
Mukhopadhyay T, Seebach D (1982) Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases. Helv Chim Acta 65(1):385–391. https://doi.org/10.1002/hlca.19820650141
Nale DB, Rana S, Parida K, Bhanage BM (2014) Amine functionalized MCM-41: an efficient heterogeneous recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles in water. Catal Sci Technol 4(6):1608–1614. https://doi.org/10.1039/c3cy00992k
Newton R, Savage GP (2008) Regioselective 1,3-dipolar cycloaddition reactions of 4-methylene-2-oxazolidinones with benzonitrile oxide. Aust J Chem 61(6):432. https://doi.org/10.1071/ch08111
Ngassam Tounzoua C, Grignard B, Brege A, Jerome C, Tassaing T, Mereau R, Detrembleur C (2020) A catalytic domino approach toward oxo-alkyl carbonates and polycarbonates from CO2, propargylic alcohols, and (mono- and di-)alcohols. ACS Sustain Chem Eng 8(26):9698–9710. https://doi.org/10.1021/acssuschemeng.0c01787
Nguyen TV, Yoo WJ, Kobayashi S (2015) Effective formylation of amines with carbon dioxide and diphenylsilane catalyzed by chelating bis(tzNHC) rhodium complexes. Angew Chem Int Ed Engl 54(32):9209–9212. https://doi.org/10.1002/anie.201504072
Niu H, Lu L, Shi R, Chiang CW, Lei A (2017) Catalyst-free N-methylation of amines using CO2. Chem Commun (Camb) 53(6):1148–1151. https://doi.org/10.1039/c6cc09072a
Nomura R, Yamamoto M, Matsuda H (1987) Preparation of cyclic ureas from carbon dioxide and diamines catalyzed by triphenylstibine oxide. Ind Eng Chem Res 26(6):1056–1059. https://doi.org/10.1021/ie00066a002
Otto A, Grube T, Schiebahn S, Stolten D (2015) Closing the loop: captured CO2 as a feedstock in the chemical industry. Energy Environ Sci 8(11):3283–3297. https://doi.org/10.1039/c5ee02591e
Padwa A, Wetmore SI (1974) Photochemical transformations of small ring heterocyclic systems. LVI Photoextrusion of carbon dioxide from the DELTA. 3-oxazolin-5-one system. J Am Chem Soc 96(8):2414–2421. https://doi.org/10.1021/ja00815a019
Pandit N, Singla RK, Shrivastava B (2012) Current updates on oxazolidinone and its significance. Int J Med Chem 2012:159285. https://doi.org/10.1155/2012/159285
Phatake VV, Ahire JP, Bhanage BM (2020) L-Serine@ZnO as an efficient and reusable catalyst for synthesis of cyclic carbonates and formamides in presence of CO2 atmosphere. Mol Catal 492:111000. https://doi.org/10.1016/j.mcat.2020.111000
Phatake VV, Mishra AA, Bhanage BM (2020) UiO-66 as an efficient catalyst for N-formylation of amines with CO2 and dimethylamine borane as a reducing agent. Inorg Chim Acta 501:119274. https://doi.org/10.1016/j.ica.2019.119274
Phung C, Ulrich RM, Ibrahim M, Tighe NTG, Lieberman DL, Pinhas AR (2011) The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide. Green Chem 13(11):3224. https://doi.org/10.1039/c1gc15850c
Pramudita RA, Motokura K (2018) Transformative reduction of carbon dioxide through organocatalysis with silanes. Green Chem 20(21):4834–4843. https://doi.org/10.1039/c8gc02052c
Pulla S, Felton CM, Ramidi P, Gartia Y, Ali N, Nasini UB, Ghosh A (2013) Advancements in oxazolidinone synthesis utilizing carbon dioxide as a C1 source. J CO2 Util 2:49–57. https://doi.org/10.1016/j.jcou.2013.07.005
Qi C-R, Jiang H-F (2007) Efficient synthesis of β-oxopropylcarbamates in compressed CO2 without any additional catalyst and solvent. Green Chem 9(12):1284. https://doi.org/10.1039/b707893e
Qian F, McCusker JE, Zhang Y, Main AD, Chlebowski M, Kokka M, McElwee-White L (2002) Catalytic oxidative carbonylation of primary and secondary diamines to cyclic ureas. optimization and substituent studies. J Org Chem 67(12):4086–4092. https://doi.org/10.1021/jo0109319
Qin Y, Sheng X, Liu S, Ren G, Wang X, Wang F (2015) Recent advances in carbon dioxide based copolymers. J CO2 Util 11:3–9. https://doi.org/10.1016/j.jcou.2014.10.003
Qin Y, Wang X (2019) Conversion of CO2 into polymers. Green Chem Chem Eng. https://doi.org/10.1007/978-1-4939-9060-3_1013
Rasal KB, Yadav GD (2016) La–Mg mixed oxide as a highly basic water resistant catalyst for utilization of CO2 in the synthesis of quinazoline-2,4(1H,3H)-dione. RSC Advances 6(112):111079–111089. https://doi.org/10.1039/c6ra15802a
Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94(8):2319–2358. https://doi.org/10.1021/cr00032a005
Roberts RR, Williams LAD (1991) Acaricidal and insecticidal activities of three synthetic oxazolidinones. Pestic Sci 33(3):393–398. https://doi.org/10.1002/ps.2780330312
Sabet-Sarvestani H, Eshghi H, Izadyar M, Noroozi-Shad N, Bakavoli M, Ziaee F (2016) Borohydride salts as high efficiency reducing reagents for carbon dioxide transformation to methanol: theoretical approach. Int J Hydrogen Energy 41(26):11131–11140. https://doi.org/10.1016/j.ijhydene.2016.05.050
Sadeghzadeh SM (2016) Spidery catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones. Catal Sci Technol 6(5):1435–1441. https://doi.org/10.1039/c5cy01543j
Safaei HR, Khastkhoda T, Shekouhy M (2018) A New highly efficient method for the catalyst-free synthesis of conjoined twins 1,6-dioxaspiro derivatives through double reaction of carbon dioxide in one reaction. ChemistrySelect 3(23):6273–6278. https://doi.org/10.1002/slct.201801082
Sakakura T, Choi JC, Yasuda H (2007) Transformation of carbon dioxide. Chem Rev 107(6):2365–2387. https://doi.org/10.1021/cr068357u
Santoyo BM, Gonzalez-Romero C, Zarate-Zarate D, Hernandez-Benitez RI, Pelayo V, Barrera E, Escalante CH, Fuentes-Benites A, Martinez-Morales G, Lopez J, Vazquez MA, Delgado F, Jimenez-Vazquez HA, Tamariz J (2019) Enantiopure 4-oxazolin-2-ones and 4-methylene-2-oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles. Chirality 31(9):719–749. https://doi.org/10.1002/chir.23109
Saptal VB, Juneja G, Bhanage BM (2018) B(C6F5)3: a robust catalyst for the activation of CO2 and dimethylamine borane for the N-formylation reactions. New J Chem 42(19):15847–15851. https://doi.org/10.1039/c8nj02816h
Saptal VB, Sasaki T, Bhanage BM (2018) Ru@PsIL-catalyzed synthesis of N-formamides and benzimidazole by using carbon dioxide and dimethylamine borane. ChemCatChem 10(12):2593–2600. https://doi.org/10.1002/cctc.201800185
Sasaki Y, Dixneuf PH (1987) Ruthenium-catalyzed reaction of carbon dioxide, amine, and acetylenic alcohol. J Org Chem 52(19):4389–4391. https://doi.org/10.1021/jo00228a046
Seki T, Kokubo Y, Ichikawa S, Suzuki T, Kayaki Y, Ikariya T (2009) Mesoporous silica-catalysed continuous chemical fixation of CO2 with N, N’-dimethylethylenediamine in supercritical CO2: the efficient synthesis of 1,3-dimethyl-2-imidazolidinone. Chem Commun (Camb) 3:349–351. https://doi.org/10.1039/b817879h
Sheldon RA (2005) Green solvents for sustainable organic synthesis: state of the art. Green Chem 7(5):267. https://doi.org/10.1039/b418069k
Sheldon RA, Brady D (2019) Broadening the scope of biocatalysis in sustainable organic synthesis. Chemsuschem 12(13):2859–2881. https://doi.org/10.1002/cssc.201900351
Shen Q, Chen X, Tan Y, Chen J, Chen L, Tan S (2019) Metal-free N-formylation of amines with CO2 and Hydrosilane by nitrogen-doped graphene nanosheets. ACS Appl Mater Interfaces 11(42):38838–38848. https://doi.org/10.1021/acsami.9b14509
Shyshkanov S, Nguyen TN, Chidambaram A, Stylianou KC, Dyson PJ (2019) Frustrated Lewis pair-mediated fixation of CO2 within a metal-organic framework. Chem Commun (Camb) 55(73):10964–10967. https://doi.org/10.1039/c9cc04374h
Simon MO, Li CJ (2012) Green chemistry oriented organic synthesis in water. Chem Soc Rev 41(4):1415–1427. https://doi.org/10.1039/c1cs15222j
Singh G, Lee J, Karakoti A, Bahadur R, Yi J, Zhao D, AlBahily K, Vinu A (2020) Emerging trends in porous materials for CO2 capture and conversion. Chem Soc Rev 49(13):4360–4404. https://doi.org/10.1039/d0cs00075b
Soga K, Chiang W-Y, Ikeda S (1974) Copolymerization of carbon dioxide with propyleneimine. J Polym Sci Polym Chem Ed 12(1):121–131. https://doi.org/10.1002/pol.1974.170120111
Soga K, Hosoda S, Ikeda S (1974) Copolymerization of carbon dioxide and ethyleneimine. Die Makromolekulare Chem 175(11):3309–3313. https://doi.org/10.1002/macp.1974.021751122
Soldi L, Massera C, Costa M, Della Ca N (2014) A novel one-pot synthesis of oxazolidinones through direct introduction of CO2 into allylamine derivatives. Tetrahedron Lett 55(7):1379–1383. https://doi.org/10.1016/j.tetlet.2014.01.029
Song B, He B, Qin A, Tang BZ (2017) Direct polymerization of carbon dioxide, diynes, and alkyl dihalides under mild reaction conditions. Macromolecules 51(1):42–48. https://doi.org/10.1021/acs.macromol.7b02109
Song Q-W, Zhou Z-H, He L-N (2017) Efficient, selective and sustainable catalysis of carbon dioxide. Green Chem 19(16):3707–3728. https://doi.org/10.1039/c7gc00199a
Stephan DW (2008) “Frustrated Lewis pairs”: a concept for new reactivity and catalysis. Org Biomol Chem 6(9):1535–1539. https://doi.org/10.1039/b802575b
Stephan DW, Erker G (2015) Frustrated Lewis pair chemistry: development and perspectives. Angew Chem Int Ed Engl 54(22):6400–6441. https://doi.org/10.1002/anie.201409800
Stolle A, Szuppa T, Leonhardt SE, Ondruschka B (2011) Ball milling in organic synthesis: solutions and challenges. Chem Soc Rev 40(5):2317–2329. https://doi.org/10.1039/c0cs00195c
Su T-m, Qin Z-z, Ji H-b, Jiang Y-x, Huang G (2015) Recent advances in the photocatalytic reduction of carbon dioxide. Environ Chem Lett 14(1):99–112. https://doi.org/10.1007/s10311-015-0528-0
Sun J-F, Wu J-T, Xu Q-Q, Zhou D, Yin J-Z (2020) CO2 electrochemical reduction using single-atom catalysts preparation, characterization and anchoring strategies: a review. Environ Chem Lett 18(5):1593–1623. https://doi.org/10.1007/s10311-020-01023-8
Tambe PR, Yadav GD (2017) Selective carbonylation of o-phenylene diamine using carbon dioxide as feedstock for synthesis of 1, 3-dihydro-benzimidazol-2-one over La–Zr mixed oxide. J Clea Prod 166:285–298. https://doi.org/10.1016/j.jclepro.2017.08.025
Tamura M, Noro K, Honda M, Nakagawa Y, Tomishige K (2013) Highly efficient synthesis of cyclic ureas from CO2 and diamines by a pure CeO2 catalyst using a 2-propanol solvent. Green Chem 15(6):1567. https://doi.org/10.1039/c3gc40495a
Tang DYY, Yew GY, Koyande AK, Chew KW, Vo D-VN, Show PL (2020) Green technology for the industrial production of biofuels and bioproducts from microalgae: a review. Environ Chem Lett. https://doi.org/10.1007/s10311-020-01052-3
Tang F, Wang L, Liu Y-N (2019) Biomass-derived N-doped porous carbon: an efficient metal-free catalyst for methylation of amines with CO2. Green Chem 21(23):6252–6257. https://doi.org/10.1039/c9gc03277k
Tazuke S, Kazama S, Kitamura N (1986) Reductive photocarboxylation of aromatic hydrocarbons. J Org Chem 51(24):4548–4553. https://doi.org/10.1021/jo00374a011
Tazuke S, Ozawa H (1975) Photofixation of carbon dioxide: formation of 9,10-dihydrophenanthrene-9-carboxylic acid from phenanthrene–amine–carbon dioxide systems. J Chem Soc Chem Commun. https://doi.org/10.1039/c39750000237
Trott G, Saini PK, Williams CK (2016) Catalysts for CO2/epoxide ring-opening copolymerization. Philos Trans A Math Phys Eng Sci. https://doi.org/10.1098/rsta.2015.0085
Truong CC, Kim J, Lee Y, Kim YJ (2017) Well-Defined cesium benzotriazolide as an active catalyst for generating disubstituted ureas from carbon dioxide and amines. ChemCatChem 9(2):247–252. https://doi.org/10.1002/cctc.201601320
Truong CC, Mishra DK (2020) Recent advances in the catalytic fixation of carbon dioxide to value-added chemicals over alkali metal salts. J CO2 Util 41:101252. https://doi.org/10.1016/j.jcou.2020.101252
Varma RS (2016) Greener and sustainable trends in synthesis of organics and nanomaterials. ACS Sustain Chem Eng 4(11):5866–5878. https://doi.org/10.1021/acssuschemeng.6b01623
Vessally E, Babazadeh M, Hosseinian A, Arshadi S, Edjlali L (2017) Nanocatalysts for chemical transformation of carbon dioxide. J CO2 Util 21:491–502. https://doi.org/10.1016/j.jcou.2017.08.014
Vessally E, Soleimani-Amiri S, Hosseinian A, Edjlali L, Babazadeh M (2017) Chemical fixation of CO2 to 2-aminobenzonitriles: a straightforward route to quinazoline-2,4(1H,3H)-diones with green and sustainable chemistry perspectives. J CO2 Util 21:342–352. https://doi.org/10.1016/j.jcou.2017.08.006
Vrancken E, Alouane N, Boutier A, Baron C, Mangeney P (2006) Remarkably efficient charcoal-promoted ring-closing carbonylations. Synthesis 2006(05):885–889. https://doi.org/10.1055/s-2006-926340
Wang H, Xin Z, Li Y (2017) Synthesis of ureas from CO2. Top Curr Chem (Cham) 375(2):49. https://doi.org/10.1007/s41061-017-0137-4
Wang S, Xi C (2019) Recent advances in nucleophile-triggered CO2-incorporated cyclization leading to heterocycles. Chem Soc Rev 48(1):382–404. https://doi.org/10.1039/c8cs00281a
Wartik T, Pearson RK (1958) Reactions of carbon dioxide with sodium and lithium borohydrides. J Inorg Nucl Chem 7(4):404–411. https://doi.org/10.1016/0022-1902(58)80250-x
Wu H, Dai W, Saravanamurugan S, Li H, Yang S (2020) Endogenous X-CO species enable catalyst-free formylation prerequisite for CO2 reductive upgrading. Green Chem 22(17):5822–5832. https://doi.org/10.1039/d0gc02142c
Wu P, Cheng H, Wang Y, Shi R, Wu Z, Arai M, Zhao F (2020) A new kind of thermoplastic polyurea elastomers synthesized from CO2 and the self-healing properties. ACS Sustain Chem Eng. https://doi.org/10.1021/acssuschemeng.0c04732
Wu Y, Jiang Z, Lu X, Liang Y, Wang H (2019) Domino electroreduction of CO2 to methanol on a molecular catalyst. Nature 575(7784):639–642. https://doi.org/10.1038/s41586-019-1760-8
Xiang X, Guo L, Wu X, Ma X, Xia Y (2012a) Reduction of carbon dioxide into tetraiodomethane at 1 atm. Environ Chem Lett 10(4):413–418. https://doi.org/10.1007/s10311-012-0379-x
Xiang X, Guo L, Wu X, Ma X, Xia Y (2012b) Urea formation from carbon dioxide and ammonia at atmospheric pressure. Environ Chem Lett 10(3):295–300. https://doi.org/10.1007/s10311-012-0366-2
Xu JX, Zhao JW, Jia ZB (2011) Efficient catalyst-free chemical fixation of carbon dioxide into 2-oxazolidinones under supercritical condition. Chin Chem Lett 22(9):1063–1066. https://doi.org/10.1016/j.cclet.2011.04.004
Xu M, Jupp AR, Ong MSE, Burton KI, Chitnis SS, Stephan DW (2019) Synthesis of urea derivatives from CO2 and silylamines. Angew Chem 131(17):5763–5767. https://doi.org/10.1002/ange.201900058
Yaashikaa PR, Senthil Kumar P, Varjani SJ, Saravanan A (2019) A review on photochemical, biochemical and electrochemical transformation of CO2 into value-added products. J CO2 Util 33:131–147. https://doi.org/10.1016/j.jcou.2019.05.017
Yan M, Kawamata Y, Baran PS (2017) Synthetic organic electrochemical methods since 2000: on the verge of a renaissance. Chem Rev 117(21):13230–13319. https://doi.org/10.1021/acs.chemrev.7b00397
Yang L, Wang H (2014) Recent advances in carbon dioxide capture, fixation, and activation by using N-heterocyclic carbenes. Chemsuschem 7(4):962–998. https://doi.org/10.1002/cssc.201301131
Yang Y, Lee JW (2019) Toward ideal carbon dioxide functionalization. Chem Sci 10(14):3905–3926. https://doi.org/10.1039/c8sc05539d
Ye S, Wang S, Lin L, Xiao M, Meng Y (2019) CO2 derived biodegradable polycarbonates: synthesis, modification and applications. Adv Ind Eng Polym Res 2(4):143–160. https://doi.org/10.1016/j.aiepr.2019.09.004
Yeung CS (2019) Photoredox catalysis as a strategy for CO2 Incorporation: direct access to carboxylic acids from a renewable feedstock. Angew Chem Int Ed Engl 58(17):5492–5502. https://doi.org/10.1002/anie.201806285
Yi W, Zeng X, Gao S (2018) Pot economy synthesis. Green Tech Org Synth Med Chem. https://doi.org/10.1002/9781119288152.ch16
Ying Z, Dong Y, Wang J, Yu Y, Zhou Y, Sun Y, Zhang C, Cheng H, Zhao F (2016) Carbon dioxide as a sustainable resource for macrocyclic oligourea. Green Chem 18(8):2528–2533. https://doi.org/10.1039/c5gc02830b
Ying Z, Zhang C, Jiang S, Wu Q, Zhang B, Yu Y, Lan M, Cheng H, Zhao F (2016) Synthesis of a novel hydrophobic polyurea gel from CO2 and amino-modified polysiloxane. J CO2 Util 15:131–135. https://doi.org/10.1016/j.jcou.2016.05.002
Ying Z, Zhao L, Zhang C, Yu Y, Liu T, Cheng H, Zhao F (2015) Utilization of carbon dioxide to build a basic block for polymeric materials: an isocyanate-free route to synthesize a soluble oligourea. RSC Adv 5(52):42095–42100. https://doi.org/10.1039/c5ra02819a
Zappia G, Menendez P, Monache GD, Misiti D, Nevola L, Botta B (2007) The contribution of oxazolidinone frame to the biological activity of pharmaceutical drugs and natural products. Mini Rev Med Chem 7(4):389–409. https://doi.org/10.2174/138955707780363783
Zhang J, Sun J, Zhang X, Zhao Y, Zhang S (2011) The recent development of CO2 fixation and conversion by ionic liquid. Greenh Gases Sci Technol 1(2):142–159. https://doi.org/10.1002/ghg.13
Zhang Y, Wang J, Zhu H, Tu T (2018) N-Formylation of amines with CO2 and H2 by using NHC-Iridium coordination assemblies as solid molecular catalysts. Chem Asian J 13(20):3018–3021. https://doi.org/10.1002/asia.201800953
Zhang Y, Zhang T, Das S (2020) Catalytic transformation of CO2 into C1 chemicals using hydrosilanes as a reducing agent. Green Chem 22(6):1800–1820. https://doi.org/10.1039/c9gc04342j
Zhang Z, Ye JH, Wu DS, Zhou YQ, Yu DG (2018) Synthesis of oxazolidin-2-ones from unsaturated amines with CO2 by using homogeneous catalysis. Chem Asian J 13(17):2292–2306. https://doi.org/10.1002/asia.201800672
Zhao LL, Wang SY, Xu XP, Ji SJ (2013) Dual 1,3-dipolar cycloaddition of carbon dioxide: two C=O bonds of CO2 react in one reaction. Chem Commun (Camb) 49(25):2569–2571. https://doi.org/10.1039/c3cc38526d
Zhao Q-N, Song Q-W, Liu P, Zhang K, Hao J (2018) Ag(I)/(C2H5)4NCl cooperation catalysis for fixing CO2 or its derivatives into β-Oxopropylcarbamates. ChemistrySelect 3(24):6897–6901. https://doi.org/10.1002/slct.201801422
Zhao TX, Zhai GW, Liang J, Li P, Hu XB, Wu YT (2017) Catalyst-free N-formylation of amines using BH3NH3 and CO2 under mild conditions. Chem Commun (Camb) 53(57):8046–8049. https://doi.org/10.1039/c7cc03860g
Zhao W, Chi X, Li H, He J, Long J, Xu Y, Yang S (2019) Eco-friendly acetylcholine-carboxylate bio-ionic liquids for controllable N-methylation and N-formylation using ambient CO2 at low temperatures. Green Chem 21(3):567–577. https://doi.org/10.1039/c8gc03549k
Zhao Y, Zhang Z (2015) Thermodynamic properties of CO2 conversion by sodium borohydride. Chem Eng Technol 38(1):110–116. https://doi.org/10.1002/ceat.201400292
Zhou D, Yu M, Fan Y, Wang Z, Dang G, Zhang Q, Xie J (2020) Sodium-induced solid-phase hydrogenation of carbon dioxide to formate by mechanochemistry. Environ Chem Lett 18(3):905–909. https://doi.org/10.1007/s10311-020-00974-2
Zou Q, Long G, Zhao T, Hu X (2020) Catalyst-free selective N-formylation and N-methylation of amines using CO2 as a sustainable C1 source. Green Chem 22(4):1134–1138. https://doi.org/10.1039/c9gc03637g
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Truong, C.C., Mishra, D.K. Catalyst-free fixation of carbon dioxide into value-added chemicals: a review. Environ Chem Lett 19, 911–940 (2021). https://doi.org/10.1007/s10311-020-01121-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-020-01121-7