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Recent Advances on CO2 Utilization as C1 Building Block in C-N and C-O Bond Formation

Synthesis of N-Formyl Amines, N-Methylamines, and Dialkoxymethanes

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Organometallics for Green Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 63))

Abstract

In the last decade, enormous efforts have been initiated to establish catalytic transformations with carbon dioxide (CO2) as a C1 building block toward the synthesis of value-added products. The scientific development was largely based on the design of tailored molecular catalysts and ligands, making novel synthetic pathways with CO2 as substrate achievable. Herein, recent applications using CO2 for the homogeneous catalyzed formation of C-N and C-O bonds within the synthesis of formamides, methylamines, and dialkoxymethanes are summarized, focusing on the construction of value-added intermediates and products.

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References

  1. Das Neves Gomes C, Jacquet O, Villiers C, Thuéry P, Ephritikhine M, Cantat T (2012). Angew Chem Int Ed 51:187

    Article  CAS  Google Scholar 

  2. Klankermayer J, Wesselbaum S, Beydoun K, Leitner W (2016). Angew Chem Int Ed 55:7296

    Article  CAS  Google Scholar 

  3. Jessop PG (2007) Homogeneous hydrogenation of carbon dioxide. In: Vries JG, Elsevier CJ (eds) The handbook of homogeneous hydrogenation. Wiley-VCH, Weinheim, p 489

    Google Scholar 

  4. Sakakura T, Choi J-C, Yasuda H (2007). Chem Rev 107:2365

    Article  CAS  PubMed  Google Scholar 

  5. Aresta M (2010) Carbon dioxide as chemical feedstock. Wiley-VCH, Weinheim

    Book  Google Scholar 

  6. Peters M, Köhler B, Kuckshinrichs W, Leitner W, Markewitz P, Müller TE (2011). ChemSusChem 4:1216

    Article  CAS  PubMed  Google Scholar 

  7. Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kühn FE (2011). Angew Chem Int Ed 50:8510

    Article  CAS  Google Scholar 

  8. Hölscher M, Keim W, Gürtler C, Müller TE, Peters M, Leitner W (2012). Z Naturforsch B 67:961

    Article  Google Scholar 

  9. Centi G, Quadrelli EA, Perathoner S (2013). Energy Environ Sci 6:1711

    Article  CAS  Google Scholar 

  10. Aresta M, Dibenedetto A, Angelini A (2014). Chem Rev 114:1709

    Article  CAS  PubMed  Google Scholar 

  11. Barbato L, Centi G, Iaquaniello G, Mangiapane A, Perathoner S (2014). Energ Technol 2:453

    Article  CAS  Google Scholar 

  12. Perathoner S, Centi G (2014). ChemSusChem 7:1274

    Article  CAS  PubMed  Google Scholar 

  13. Plass L, Bertau M, Linicus M, Heyde R, Weingart E (2014) Methanol as a hydrogen and energy carrier. In: Bertau M, Offermanns H, Plass L, Schmidt F, Wernicke H-J (eds) Methanol: the basic chemical and energy feedstock of the future. Springer, Heidelberg, p 619

    Chapter  Google Scholar 

  14. Bourasseau C, Guinot B (2015) Hydrogen: a storage means for renewable energies. In: Godula-Jopek A (ed) Hydrogen production. Wiley-VCH, Weinheim, p 311

    Google Scholar 

  15. Ausfelder F, Beilmann C, Bertau M, Bräuninger S, Heinzel A, Hoer R, Koch W, Mahlendorf F, Metzelthin A, Peuckert M, Plass L, Räuchle K, Reuter M, Schaub G, Schiebahn S, Schwab E, Schüth F, Stolten D, Teßmer G, Wagemann K, Ziegahn K-F (2015). Chem Ing Tech 87:17

    Article  CAS  Google Scholar 

  16. Junge H, Rockstroh N, Fischer S, Brückner A, Ludwig R, Lochbrunner S, Kühn O, Beller M (2017). Inorganics 5:14

    Article  CAS  Google Scholar 

  17. Duan J, Chen S, Zhao C (2017). Nat Commun 8:15341

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Yao S, Zhang X, Zhou W, Gao R, Xu W, Ye Y, Lin L, Wen X, Liu P, Chen B, Crumlin E, Guo J, Zuo Z, Li W, Xie J, Lu L, Kiely CJ, Gu L, Shi C, Rodriguez JA, Ma D (2017). Science 357:389

    Article  CAS  PubMed  Google Scholar 

  19. Leitner W, Quadrelli EA, Schlogl R (2017). Green Chem 19:2307

    Article  CAS  Google Scholar 

  20. Schieweck BG, Klankermayer J (2017). Angew Chem Int Ed 56:10854

    Article  CAS  Google Scholar 

  21. Deutz S, Bongartz D, Heuser B, Kätelhön A, Schulze Langenhorst L, Omari A, Walters M, Klankermayer J, Leitner W, Mitsos A, Pischinger S, Bardow A (2018). Energy Environ Sci 11:331

    Article  CAS  Google Scholar 

  22. Thenert K, Beydoun K, Wiesenthal J, Leitner W, Klankermayer J (2016). Angew Chem Int Ed 55:12266

    Article  CAS  Google Scholar 

  23. Hett R, Fang QK, Gao Y, Wald SA, Senanayake CH (1998). Org Process Res Dev 2:96

    Article  CAS  Google Scholar 

  24. Kazuhiro K, Satoshi N, Masataka K, Osamu M, Hisatoshi K (1995). Chem Lett 24:575

    Article  Google Scholar 

  25. Weissermel K, Arpe H-J (2008) Industrial organic chemistry3rd edn. Wiley-VCH, Weinheim

    Google Scholar 

  26. Jones S, Warner CJA (2012). Org Biomol Chem 10:2189

    Article  CAS  PubMed  Google Scholar 

  27. Bipp H, Kieczka H (2000) Formamides. Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  28. Wuts PGM (2014) Greene’s protective groups in organic synthesis5th edn. Wiley, Hoboken

    Google Scholar 

  29. Gerack C, McElwee-White L (2014). Molecules 19:7689

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  30. Olah GA, Ohannesian L, Arvanaghi M (1987). Chem Rev 87:671

    Article  CAS  Google Scholar 

  31. Arpe H-J (2010) Industrial organic chemistry, vol 5. Wiley-VCH, Weinheim

    Google Scholar 

  32. Choi Y-S, Shim YN, Lee J, Yoon JH, Hong CS, Cheong M, Kim HS, Jang HG, Lee JS (2011). Appl Catal A Gen 404:87

    Article  CAS  Google Scholar 

  33. Ortega N, Richter C, Glorius F (2013). Org Lett 15:1776

    Article  CAS  PubMed  Google Scholar 

  34. Tanaka S, Minato T, Ito E, Hara M, Kim Y, Yamamoto Y, Asao N (2013). Chem Eur J 19:11832

    Article  CAS  PubMed  Google Scholar 

  35. Kang B, Hong SH (2015). Adv Synth Catal 357:834

    Article  CAS  Google Scholar 

  36. Kothandaraman J, Kar S, Sen R, Goeppert A, Olah GA, Prakash GKS (2017). J Am Chem Soc 139:2549

    Article  CAS  PubMed  Google Scholar 

  37. Chakraborty S, Gellrich U, Diskin-Posner Y, Leitus G, Avram L, Milstein D (2017). Angew Chem Int Ed 56:4229

    Article  CAS  Google Scholar 

  38. Galindo Cifre P, Badr O (2007). Energy Convers Manag 48:519

    Article  CAS  Google Scholar 

  39. Dong B, Wang L, Zhao S, Ge R, Song X, Wang Y, Gao Y (2016). Chem Commun 52:7082

    Article  CAS  Google Scholar 

  40. Nale DB, Rath D, Parida KM, Gajengi A, Bhanage BM (2016). Cat Sci Technol 6:4872

    Article  CAS  Google Scholar 

  41. Molla RA, Bhanja P, Ghosh K, Islam SS, Bhaumik A, Islam SM (2017). ChemCatChem 9:1939

    Article  CAS  Google Scholar 

  42. Luo R, Chen Y, He Q, Lin X, Xu Q, He X, Zhang W, Zhou X, Ji H (2017). ChemSusChem 10:1526

    Article  CAS  PubMed  Google Scholar 

  43. He Z, Liu H, Liu H, Qian Q, Meng Q, Mei Q, Han B (2017). ChemCatChem 9:1947

    Article  CAS  Google Scholar 

  44. Ju P, Chen J, Chen A, Chen L, Yu Y (2017). ACS Sustain Chem Eng 5:2516

    Article  CAS  Google Scholar 

  45. Zhang Y, Wang H, Yuan H, Shi F (2017). ACS Sustain Chem Eng 5:5758

    Article  CAS  Google Scholar 

  46. Mitsudome T, Urayama T, Fujita S, Maeno Z, Mizugaki T, Jitsukawa K, Kaneda K (2017). ChemCatChem 9:3632

    Article  CAS  Google Scholar 

  47. Villiers C, Dognon J-P, Pollet R, Thuéry P, Ephritikhine M (2010). Angew Chem Int Ed 49:3465

    Article  CAS  Google Scholar 

  48. Hao L, Zhao Y, Yu B, Yang Z, Zhang H, Han B, Gao X, Liu Z (2015). ACS Catal 5:4989

    Article  CAS  Google Scholar 

  49. Maryanoff BE, Reitz AB (1989). Chem Rev 89:863

    Article  CAS  Google Scholar 

  50. Li A-H, Dai L-X, Aggarwal VK (1997). Chem Rev 97:2341

    Article  CAS  PubMed  Google Scholar 

  51. Sun X-L, Tang Y (2008). Acc Chem Res 41:937

    Article  CAS  PubMed  Google Scholar 

  52. Matthews CN, Driscoll JS, Birum GH (1966) Chem Commun 736. https://doi.org/10.1039/C19660000736

  53. Zhou H, Wang G-X, Zhang W-Z, Lu X-B (2015). ACS Catal 5:6773

    Article  CAS  Google Scholar 

  54. Chong CC, Kinjo R (2015). Angew Chem Int Ed 54:12116

    Article  CAS  Google Scholar 

  55. Lu Y, Gao Z-H, Chen X-Y, Guo J, Liu Z, Dang Y, Ye S, Wang Z-X (2017). Chem Sci 8:7637

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T (2012). J Am Chem Soc 134:2934

    Article  CAS  PubMed  Google Scholar 

  57. Saptal VB, Bhanage BM (2016). ChemSusChem 9:1980

    Article  CAS  PubMed  Google Scholar 

  58. Das S, Bobbink FD, Bulut S, Soudani M, Dyson PJ (2016). Chem Commun 52:2497

    Article  CAS  Google Scholar 

  59. Bobbink FD, Das S, Dyson PJ (2017). Nat Protoc 12:417

    Article  CAS  PubMed  Google Scholar 

  60. Piel I, Pawelczyk MD, Hirano K, Fröhlich R, Glorius F (2011). Eur J Org Chem 2011:5475

    Article  CAS  Google Scholar 

  61. Hulla M, Bobbink FD, Das S, Dyson PJ (2016). ChemCatChem 8:3338

    Article  CAS  Google Scholar 

  62. Revunova K, Nikonov GI (2015). Dalton Trans 44:840

    Article  CAS  PubMed  Google Scholar 

  63. Liu X-F, Li X-Y, Qiao C, Fu H-C, He L-N (2017). Angew Chem Int Ed 56:7425

    Article  CAS  Google Scholar 

  64. Xie W, Zhao M, Cui C (2013). Organometallics 32:7440

    Article  CAS  Google Scholar 

  65. Zhao M, Xie W, Cui C (2014). Chem Eur J 20:9259

    Article  CAS  PubMed  Google Scholar 

  66. Liu X-F, Qiao C, Li X-Y, He L-N (2017). Green Chem 19:1726

    Article  CAS  Google Scholar 

  67. Aue DH, Webb HM, Bowers MT (1976). J Am Chem Soc 98:318

    Article  CAS  Google Scholar 

  68. Reichardt C (1994). Chem Rev 94:2319

    Article  CAS  Google Scholar 

  69. Lv H, Xing Q, Yue C, Lei Z, Li F (2016). Chem Commun 52:6545

    Article  CAS  Google Scholar 

  70. Song J, Zhou B, Liu H, Xie C, Meng Q, Zhang Z, Han B (2016). Green Chem 18:3956

    Article  CAS  Google Scholar 

  71. Zhao T-X, Zhai G-W, Liang J, Li P, Hu X-B, Wu Y-T (2017). Chem Commun 53:8046

    Article  CAS  Google Scholar 

  72. Zhang X, Kam L, Trerise R, Williams TJ (2017). Acc Chem Res 50:86

    Article  CAS  PubMed  Google Scholar 

  73. Hao L, Zhang H, Luo X, Wu C, Zhao Y, Liu X, Gao X, Chen Y, Liu Z (2017). J CO2 Util 22:208

    Article  CAS  Google Scholar 

  74. Frogneux X, Jacquet O, Cantat T (2014). Cat Sci Technol 4:1529

    Article  CAS  Google Scholar 

  75. Pouessel J, Jacquet O, Cantat T (2013). ChemCatChem 5:3552

    Article  CAS  Google Scholar 

  76. Motokura K, Takahashi N, Kashiwame D, Yamaguchi S, Miyaji A, Baba T (2013). Cat Sci Technol 3:2392

    Article  CAS  Google Scholar 

  77. Itagaki S, Yamaguchi K, Mizuno N (2013). J Mol Catal A Chem 366:347

    Article  CAS  Google Scholar 

  78. Zhang S, Mei Q, Liu H, Liu H, Zhang Z, Han B (2016). RSC Adv 6:32370

    Article  CAS  Google Scholar 

  79. Motokura K, Takahashi N, Miyaji A, Sakamoto Y, Yamaguchi S, Baba T (2014). Tetrahedron 70:6951

    Article  CAS  Google Scholar 

  80. Shintani R, Nozaki K (2013). Organometallics 32:2459

    Article  CAS  Google Scholar 

  81. Lu X-B (2016) Carbon dioxide and organometallics. Springer, Cham

    Book  Google Scholar 

  82. González-Sebastián L, Flores-Alamo M, Garcıa JJ (2013). Organometallics 32:7186

    Article  CAS  Google Scholar 

  83. Motokura K, Kashiwame D, Miyaji A, Baba T (2012). Org Lett 14:2642

    Article  CAS  PubMed  Google Scholar 

  84. Sattler W, Parkin G (2012). J Am Chem Soc 134:17462

    Article  CAS  PubMed  Google Scholar 

  85. Nguyen TV, Yoo WJ, Kobayashi S (2015). Angew Chem Int Ed 54:9209

    Article  CAS  Google Scholar 

  86. Luo R, Lin X, Chen Y, Zhang W, Zhou X, Ji H (2017). ChemSusChem 10:1224

    Article  CAS  PubMed  Google Scholar 

  87. Luo R, Lin X, Lu J, Zhou X, Ji H (2017). Chin J Catal 38:1382

    Article  CAS  Google Scholar 

  88. Jessop PG, Ikariya T, Noyori R (1995). Chem Rev 95:259

    Article  CAS  Google Scholar 

  89. Schmid L, Schneider MS, Engel D, Baiker A (2003). Catal Lett 88:105

    Article  CAS  Google Scholar 

  90. Farlow MW, Adkins H (1935). J Am Chem Soc 57:2222

    Article  CAS  Google Scholar 

  91. Haynes P, Slaugh LH, Kohnle JF (1970) Tetrahedron Lett 365

    Google Scholar 

  92. Jessop PG, Hsiao Y, Ikariya T, Noyori R (1994). J Am Chem Soc 116:8851

    Article  CAS  Google Scholar 

  93. Kröcher O, Köppel RA, Baiker A (1997) Chem Commun 453. https://doi.org/10.1039/A608150I

  94. Munshi P, Heldebrant DJ, McKoon EP, Kelly PA, Tai C-C, Jessop PG (2003). Tetrahedron Lett 44:2725

    Article  CAS  Google Scholar 

  95. Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller M (2010). Angew Chem Int Ed 49:9777

    Article  CAS  Google Scholar 

  96. Jayarathne U, Hazari N, Bernskoetter WH (2018). ACS Catal 8:1338

    Article  CAS  Google Scholar 

  97. Federsel C, Ziebart C, Jackstell R, Baumann W, Beller M (2012). Chem Eur J 18:72

    Article  CAS  PubMed  Google Scholar 

  98. Ziebart C, Federsel C, Anbarasan P, Jackstell R, Baumann W, Spannenberg A, Beller M (2012). J Am Chem Soc 134:20701

    Article  CAS  PubMed  Google Scholar 

  99. Kröcher O, Köppel RA, Baiker A (1996) Chem Commun 1497. https://doi.org/10.1039/CC9960001497

  100. Schmid L, Rohr M, Baiker A (1999) Chem Commun 2303. https://doi.org/10.1039/A906956I

  101. Kayaki Y, Shimokawatoko Y, Ikariya T (2003). Adv Synth Catal 345:175

    Article  CAS  Google Scholar 

  102. Baffert M, Maishal TK, Mathey L, Copéret C, Thieuleux C (2011). ChemSusChem 4:1762

    Article  CAS  PubMed  Google Scholar 

  103. Zhang L, Han Z, Zhao X, Wang Z, Ding K (2015). Angew Chem Int Ed 54:6186

    Article  CAS  Google Scholar 

  104. Liu H, Mei Q, Xu Q, Song J, Liu H, Han B (2017). Green Chem 19:196

    Article  CAS  Google Scholar 

  105. Daw P, Chakraborty S, Leitus G, Diskin-Posner Y, Ben-David Y, Milstein D (2017). ACS Catal 7:2500

    Article  CAS  Google Scholar 

  106. Kar S, Goeppert A, Kothandaraman J, Prakash GKS (2017). ACS Catal 7:6347

    Article  CAS  Google Scholar 

  107. Dubey A, Nencini L, Fayzullin RR, Nervi C, Khusnutdinova JR (2017). ACS Catal 7:3864

    Article  CAS  Google Scholar 

  108. Affan MA, Jessop PG (2017). Inorg Chem 56:7301

    Article  CAS  PubMed  Google Scholar 

  109. Jessop PG, Hsiao Y, Ikariya T, Noyori R (1996). J Am Chem Soc 118:344

    Article  CAS  Google Scholar 

  110. Schmid L, Canonica A, Baiker A (2003). Appl Catal A Gen 255:23

    Article  CAS  Google Scholar 

  111. Kröcher O, Köppel RA, Fröba M, Baiker A (1998). J Catal 178:284

    Article  Google Scholar 

  112. Kröcher O, Köppel RA, Baiker A (1999). J Mol Catal A Chem 140:185

    Article  Google Scholar 

  113. Behr A, Ebbinghaus P, Naendrup F (2004). Chem Eng Technol 27:495

    Article  CAS  Google Scholar 

  114. Liu F, Abrams MB, Baker RT, Tumas W (2001) Chem Commun 433. https://doi.org/10.1039/B009701M

  115. Pazicky M, Schaub T, Paciello R, Lissner A (2013) DE102012019441A1, 11 Apr 2013

    Google Scholar 

  116. Seayad J, Tillack A, Hartung CG, Beller M (2002). Adv Synth Catal 344:795

    Article  CAS  Google Scholar 

  117. Pohlki F, Doye S (2003). Chem Soc Rev 32:104

    Article  CAS  PubMed  Google Scholar 

  118. Lygaitis R, Getautis V, Grazulevicius JV (2008). Chem Soc Rev 37:770

    Article  CAS  PubMed  Google Scholar 

  119. Fuglseth E, Otterholt E, Høgmoen H, Sundby E, Charnock C, Hoff BH (2009). Tetrahedron 65:9807

    Article  CAS  Google Scholar 

  120. Song L, Jiang X, Wang L (2011). J Chromatogr B Anal Technol Biomed Life Sci 879:3658

    Article  CAS  Google Scholar 

  121. van Gysel AB, Musin W (2000) Methylamines. Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  122. Farkas E, Sunman CJ (1985). J Org Chem 50:1110

    Article  CAS  Google Scholar 

  123. Hailes HC (2001). Appl Organomet Chem 15:315

    Article  CAS  Google Scholar 

  124. Tundo P, Selva M (2002). Acc Chem Res 35:706

    Article  CAS  PubMed  Google Scholar 

  125. Zhao Y, Foo SW, Saito S (2011). Angew Chem Int Ed 50:3006

    Article  CAS  Google Scholar 

  126. Cabrero-Antonino JR, Adam R, Junge K, Beller M (2016). Cat Sci Technol 6:7956

    Article  CAS  Google Scholar 

  127. Das D, Khan HPA, Shivahare R, Gupta S, Sarkar J, Siddiqui MI, Ampapathi RS, Chakraborty TK (2017). Org Biomol Chem 15:3337

    Article  CAS  PubMed  Google Scholar 

  128. Zheng J, Darcel C, Sortais J-B (2014). Chem Commun 50:14229

    Article  CAS  Google Scholar 

  129. Eschweiler W (1905). Ber Dtsch Chem Ges 38:880

    Article  Google Scholar 

  130. Clarke HT, Gillespie HB, Weisshaus SZ (1933). J Am Chem Soc 55:4571

    Article  CAS  Google Scholar 

  131. Schreiner S, Yu JY, Vaska L (1988). Inorg Chim Acta 147:139

    Article  CAS  Google Scholar 

  132. Vaska L, Schreiner S, Felty RA, Yu JY (1989). J Mol Catal 52:11

    Article  Google Scholar 

  133. Klankermayer J, Leitner W (2015). Science 350:629

    Article  CAS  PubMed  Google Scholar 

  134. Gredig SV, Koeppel RA, Baiker A (1995) J Chem Soc Chem Commun 73

    Google Scholar 

  135. Gredig SV, Koeppel R, Baiker A (1996). Catal Today 29:339

    Article  CAS  Google Scholar 

  136. Gredig SV, Koeppel R, Baiker A (1997). Appl Catal A Gen 162:249

    Article  CAS  Google Scholar 

  137. Cui X, Dai X, Zhang Y, Deng Y, Shi F (2014). Chem Sci 5:649

    Article  CAS  Google Scholar 

  138. Cui X, Zhang Y, Deng Y, Shi F (2014). Chem Commun 50:13521

    Article  CAS  Google Scholar 

  139. Kon K, Siddiki SM, Onodera W, Shimizu K (2014). Chem Eur J 20:6264

    Article  CAS  PubMed  Google Scholar 

  140. Du XL, Tang G, Bao HL, Jiang Z, Zhong XH, Su DS, Wang JQ (2015). ChemSusChem 8:3489

    Article  CAS  PubMed  Google Scholar 

  141. Tamura M, Miura A, Gu Y, Nakagawa Y, Tomishige K (2017). Chem Lett 46:1243

    Article  CAS  Google Scholar 

  142. Toyao T, Siddiki S, Morita Y, Kamachi T, Touchy AS, Onodera W, Kon K, Furukawa S, Ariga H, Asakura K, Yoshizawa K, Shimizu KI (2017). Chemistry 23:14848

    Article  CAS  PubMed  Google Scholar 

  143. Hardy S, de Wispelaere IM, Leitner W, Liauw MA (2013). Analyst 138:819

    Article  CAS  PubMed  Google Scholar 

  144. Jacquet O, Frogneux X, Das Neves Gomes C, Cantat T (2013). Chem Sci 4:2127

    Article  CAS  Google Scholar 

  145. Blondiaux E, Pouessel J, Cantat T (2014). Angew Chem Int Ed 53:12186

    Article  CAS  Google Scholar 

  146. Riduan SN, Zhang Y, Ying JY (2009). Angew Chem Int Ed 48:3322

    Article  CAS  Google Scholar 

  147. Das S, Bobbink FD, Laurenczy G, Dyson PJ (2014). Angew Chem Int Ed 53:12876

    Article  CAS  Google Scholar 

  148. Yang Z, Yu B, Zhang H, Zhao Y, Ji G, Ma Z, Gao X, Liu Z (2015). Green Chem 17:4189

    Article  CAS  Google Scholar 

  149. Fang C, Lu C, Liu M, Zhu Y, Fu Y, Lin B-L (2016). ACS Catal 6:7876

    Article  CAS  Google Scholar 

  150. Niu H, Lu L, Shi R, Chiang CW, Lei A (2017). Chem Commun 53:1148

    Article  CAS  Google Scholar 

  151. Yang Z-Z, Yu B, Zhang H, Zhao Y, Ji G, Liu Z (2015). RSC Adv 5:19613

    Article  CAS  Google Scholar 

  152. Santoro O, Lazreg F, Minenkov Y, Cavallo L, Cazin CSJ (2015). Dalton Trans 44:18138

    Article  CAS  PubMed  Google Scholar 

  153. Li Y, Fang X, Junge K, Beller M (2013). Angew Chem Int Ed 52:9568

    Article  CAS  Google Scholar 

  154. González-Sebastián L, Flores-Alamo M, García JJ (2015). Organometallics 34:763

    Article  CAS  Google Scholar 

  155. Morris DS, Weetman C, Wennmacher JTC, Cokoja M, Drees M, Kuhn FE, Love JB (2017). Cat Sci Technol 7:2838

    Article  CAS  Google Scholar 

  156. Beydoun K, vom Stein T, Klankermayer J, Leitner W (2013). Angew Chem Int Ed 52:9554

    Article  CAS  Google Scholar 

  157. Klankermayer J, Beydoun K, vom Stein T, Leitner W (2015) WO2015000753A1, 8 Jan 2015

    Google Scholar 

  158. Bianchini C, Meli A, Peruzzini M, Vizza F, Zanobini F (1992). Coord Chem Rev 120:193

    Article  CAS  Google Scholar 

  159. vom Stein T, Weigand T, Merkens C, Klankermayer J, Leitner W (2013). ChemCatChem 5:439

    Article  CAS  Google Scholar 

  160. Nunez Magro AA, Eastham GR, Cole-Hamilton DJ (2007) Chem Commun 3154. https://doi.org/10.1039/B706635J

  161. Coetzee J, Dodds DL, Klankermayer J, Brosinski S, Leitner W, Slawin AMZ, Cole-Hamilton DJ (2013). Chem Eur J 19:11039

    Article  CAS  PubMed  Google Scholar 

  162. Li Y, Sorribes I, Yan T, Junge K, Beller M (2013). Angew Chem Int Ed 52:12156

    Article  CAS  Google Scholar 

  163. He Z, Liu H, Qian Q, Lu L, Guo W, Zhang L, Han B (2017) Sci China Chem 1

    Google Scholar 

  164. Beydoun K, Thenert K, Streng ES, Brosinski S, Leitner W, Klankermayer J (2016). ChemCatChem 8:135

    Article  CAS  Google Scholar 

  165. Beydoun K, Ghattas G, Thenert K, Klankermayer J, Leitner W (2014). Angew Chem Int Ed 53:11010

    Article  CAS  Google Scholar 

  166. McNeely W, Spencer CM (1998). Drugs 55:405

    Article  CAS  PubMed  Google Scholar 

  167. Singal A (2008). Expert Opin Drug Metab Toxicol 4:999

    Article  CAS  PubMed  Google Scholar 

  168. Maeda T, Yamamoto T, Takase M, Sasaki K, Arika T, Yokoo M, Hashimoto R, Amemiya K, Koshikawa S (1991) US patent 5021458, 4 June 1991

    Google Scholar 

  169. Lahaye J, Prado G (1983) Soot in combustion systems and its toxic properties. Nato conference series, series VI: material science. Plenum Press, New York, p 433

    Google Scholar 

  170. Burger J, Siegert M, Ströfer E, Hasse H (2010). Fuel 89:3315

    Article  CAS  Google Scholar 

  171. Lumpp B, Rothe D, Pastötter C, Lämmermann R, Jacob E (2011). MTZ Worldwide 72:34

    Article  Google Scholar 

  172. Burger J, Ströfer E, Hasse H (2012). Ind Eng Chem Res 51:12751

    Article  CAS  Google Scholar 

  173. Burger J, Ströfer E, Hasse H (2013). Chem Eng Res Des 91:2648

    Article  CAS  Google Scholar 

  174. Dubois J-L (2011) EP 2306816, 13 Apr 2011

    Google Scholar 

  175. Ströfer E, Schelling H, Hasse H, Blagov S (2006) WO2006134081, 21 Dec 2006

    Google Scholar 

  176. Zhu Z, Zhang J, Chen Z, He J (2012) China Patent 102557899A, 11 July 2012

    Google Scholar 

  177. Friedrich H, Neugebauer W (1974) US Patent 3843562, 22 Oct 1974

    Google Scholar 

  178. Sato S, Tanigawa Y (2000) Japan Patent 2000109443, 18 Apr 2000

    Google Scholar 

  179. Hasse H, Drunsel JO, Burger J, Schmidt U, Renner M, Blagov S (2012) WO2012062822, 18 May 2012

    Google Scholar 

  180. Hasse H, Drunsel JO, Burger J, Schmidt U, Renner M, Blagov S (2014) US Patent 20140187823, 3 July 2014

    Google Scholar 

  181. Fu Y, Shen J (2007) Chem Commun 2172

    Google Scholar 

  182. Zhan E, Li Y, Liu J, Huang X, Shen W (2009). Catal Commun 10:2051

    Article  CAS  Google Scholar 

  183. Prado NT, Nogueria FGE, Nogueira AE, Nunes CA, Diniz R, Oliveira LCA (2010). Energy Fuel 24:4793

    Article  CAS  Google Scholar 

  184. Guo H, Li D, Jiang D, Li W, Sun Y (2010). Catal Commun 11:396

    Article  CAS  Google Scholar 

  185. Zhao H, Bennici S, Shen J, Auroux A (2010). J Catal 272:176

    Article  CAS  Google Scholar 

  186. Chen S, Wang S, Ma X, Gong J (2011). Chem Commun 47:9345

    Article  CAS  Google Scholar 

  187. Lu X, Qin Z, Dong M, Zhu H, Wang G, Zhao Y, Fan W, Wang J (2011). Fuel 90:1335

    Article  CAS  Google Scholar 

  188. Nikonova OA, Capron M, Fang G, Faye J, Mamede A-S, Jalowiecki-Duhamel L, Dumeignil F, Seisenbaeva GA (2011). J Catal 279:310

    Article  CAS  Google Scholar 

  189. Thavornprasert K-a, Capron M, Jalowiecki-Duhamel L, Gardoll O, Trentesaux M, Mamede A-S, Fang G, Faye J, Touati N, Vezin H, Dubois J-L, Couturier J-L, Dumeignil F (2014). Appl Catal B Environ 145:126

    Article  CAS  Google Scholar 

  190. Li M, Long Y, Deng Z, Zhang H, Yang X, Wang G (2015). Catal Commun 68:46

    Article  CAS  Google Scholar 

  191. Zhang Q, Zhao H, Lu B, Zhao J, Cai Q (2016). J Mol Catal A Chem 421:117

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Aachen, Germany

    Kassem Beydoun & Jürgen Klankermayer

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  1. Kassem Beydoun
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  2. Jürgen Klankermayer
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Correspondence to Jürgen Klankermayer .

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  1. Organométalliques, matériaux et Catalyse, Univ Rennes, CNRS, (UMR 6226), Institut Sciences Chimiques, Rennes, France

    Pierre H. Dixneuf

  2. Organométalliques, matériaux et Catalyse, Univ Rennes, CNRS, (UMR 6226), Institut Sciences Chimiques, Rennes, France

    Jean-François Soulé

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Beydoun, K., Klankermayer, J. (2018). Recent Advances on CO2 Utilization as C1 Building Block in C-N and C-O Bond Formation. In: Dixneuf, P., Soulé, JF. (eds) Organometallics for Green Catalysis. Topics in Organometallic Chemistry, vol 63. Springer, Cham. https://doi.org/10.1007/3418_2018_16

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