Abstract
In recent years, with the rapid development of polymer science, the application of classical named reactions has transferred from small-molecule compounds to polymers. The versatility of named reactions in terms of monomer selection, solvent envi-ronment,reaction temperature, and post-modification permits the synthesis of sophisticated macromolecular structures under conditions where other reaction processes will not operate. In this review, we divided the named reactions employed in polymer-chain synthesis into three types: transition metal-catalyzed cross-coupling reactions, metal-free cross-coupling reactions,and multi-components reactions. Thus, we focused our discussion on the progress in the utilization of these named reactionsin polymer synthesis
Similar content being viewed by others
References
Kürti L, Czakó B. Strategic Applications of Named Reaction in Organic Synthesis. Amsterdam: Elsevier, 2005
Lutz JF. A controlled sequence of events. Nat Chem, 2010, 2: 84–85
Szwarc M. “Living” polymers. Nature, 1956, 176: 1168–1169
Webster OW. The discovery and commercialization of group transfer polymerization. J Polym Sci Polym Chem, 2000, 38: 2855–2860
Endo T. General mechanisms in ring-opening polymerization. In:Dubois P, Coulembier O, Raquez JM, Eds. Handbook of Ring-Opening Polymerization K GaA. Weinheim: Wiley-VCH VerlagGmbH & Co., 2009. 53
Goethals EJ, Du Prez F. Carbocationic polymerizations. Prog Polym Sci, 2007, 32: 220–246
Bielawski CW, Grubbs RH. Living ring-opening metathesis polymerization. Prog Polym Sci, 2007, 32: 1–29
Braunecker WA, Matyjaszewski K. Controlled/living radical polymerization:features, developments, and perspectives. Prog Polym Sci, 2007, 32: 93–146
Jiang XY, Jiang X, Lu GL, Feng C, Huang XY. The first amphiphilicgraft copolymer bearing a hydrophilic poly(2-hydroxylethyl acrylate)backbone synthesized by successive RAFT and ATRP. Polym Chem, 2014, 5: 4915–4925
Jiang X, Feng C, Lu GL, Huang XY. Thermoresponsive homopolymertunable by pH and CO2. ACS Macro Lett, 2014, 3: 1121–1125
Zhang YN, Wang GW, Huang JL. Synthesis of macrocyclicpoly(ethylene oxide) and polystyrene via Glaser coupling reaction. Macromolecules, 2010, 43: 10343–10347
Yao WQ, Li YJ, Feng C, Lu GL, Huang XY. Synthesis of a sunshapedamphiphilic copolymer consisting of a cyclic perfluorocyclobutylaryl ether-based backbone and lateral PMAA side chains. RSC Adv, 2014, 4: 52105–52116
Lu GL, Liu H, Gao HF, Feng C, Li YJ, Huang XY. Construction ofsemi-fluorinated amphiphilic graft copolymer bearing poly(2-methyl-1,4-bistrifluoro-vinyloxybenzene) backbone and poly(ethylene glycol)side chains via the grafting-onto strategy. RSC Adv, 2015, 5: 39668–39676
Ma H, Jen AKY, Dalton LR. Polymer-based optical waveguides:materials, processing, and devices. Adv Mater, 2002, 14: 1339–1365
Yang L, Zhou H, Price SC, You W. Parallel-like bulk heterojunctionpolymer solar cells. J Am Chem Soc, 2012, 134: 5432–5435
Zalar P, Kamkar D, Naik R, Ouchen F, Grote JG, Bazan GC, Nguyen TQ. DNA Electron injection interlayers for polymer light-emittingdiodes. J Am Chem Soc, 2011, 133: 11010–11013
Wang S, Kappl M, Liebewirth I, Müller M, Kirchhoff K, Pisula W, Müllen K. Organic field-effect transistors based on gighly orderedsingle polymer fibers. Adv Mater, 2012, 24: 417–420
Günes S, Neugebauer H, Sariciftci NS. Conjugated polymer-basedorganic solar cells. Chem Rev, 2007, 107: 1324–1338
Chochos CL, Choulis SA. How the structural deviations on thebackbone of conjugated polymers influence their optoelectronicproperties and photovoltaic performance. Prog Polym Sci, 2011, 36: 1326–1414
Yokozawa T, Yokoyama A. Chain-growth condensation polymerizationfor the synthesis of well-defined condensation polymers and?-conjugated polymers. Chem Rev, 2009, 109: 5595–5619
Xu S, Kim EH, Wei A, Negishi EI. Pd-and Ni-catalyzed crosscouplingreactions in the synthesis of organic electronic materials. SciTechnol Adv Mater, 2014, 15: 1–23
Sheina EE, Liu J, Iovu MC, Laird DW, McCullough RD. Chaingrowth mechanism for regioregular nickel-initiated cross-couplingpoly merizations. Macromolecules, 2004, 37: 3526–3528
Iovu MC, Sheina EE, Gil RR, McCullough RD. Experimental evidencefor the quasi-“living” nature of the grignard metathesis methodfor the synthesis of regioregular poly(3-alkylthiophenes). Macromolecules, 2005, 38: 8649–8656
Yokoyama A, Miyakoshi R, Yokozawa T. Chain-growth polymerizationfor poly(3-hexylthiophene) with a defined molecular weight anda low polydispersity. Macromolecules, 2004, 37: 1169–1171
Miyakoshi R, Yokoyama A, Yokozawa T. Catalyst-transfer polycondensation.Mechanism of Ni-catalyzed chain-growth polymerizationleading to well-defined poly(3-hexylthiophene). J Am Chem Soc, 2005, 127: 17542–17547
Tamao K, Sumitani K, Kumada M. Selective carbon-carbon bondformation by cross-coupling of Grignard reagents with organic halides.Catalysis by nickel-phosphine complexes. J Am Chem Soc, 1972, 94: 4374–4376
Corriu RJP, Masse JP. Activation of Grignard reagents by transitionmetalcomplexes. A new and simple synthesis of trans-stilbenes andpolyphenyls. J Chem Soc Chem Commun, 1972: 144a
Kiriy A, Senkovskyy V, Sommer M. Kumada catalyst-transfer polycondensation:mechanism, opportunities, and challenges. MacromolRapid Commun, 2011, 32: 1503–1517
Pammer F, Passlack U. Head-to-tail regioregular polythiazole preparedvia Kumada-coupling polycondensation. ACS Macro Lett, 2014, 3: 170–174
Miyaura N, Yamada K, Suzuki A. A new stereospecific crosscouplingby the palladium-catalyzed reaction of 1-alkenylboraneswith 1-alkenyl or 1-alkynyl halides. Tetrahedron Lett, 1979, 20: 3437–3440
Rehahn M, Schlüter AD, Wegner G, Feast WJ. Soluble poly(paraphenylene)s. 2. Improved synthesis of poly(para-2,5-di-n-hexylphenylene)via Pd-catalysed coupling of 4-bromo-2,5-di-n-hexylbenzeneboronicacid. Polymer, 1989, 30: 1060–1062
Sakamoto J, Rehahn M, Wegner G, Schlüter AD. Suzuki polycondensation: polyarylenes. Macromol Rapid Commun, 2009, 30: 653–687
Tsao HN, Cho D, Andreasen JW, Rouhanipour A, Breiby DW, Pisula W, Müllen K. The influence of morphology on high-performancepolymer field-effect transistors. Adv Mater, 2009, 21: 209–212
Tsao HN, Cho DM, Park I, Hansen MR, Mavrinskiy A, Yoon DY, Graf R, Pisula W, Spiess HW, Müllen K. Ultrahigh mobility in polymerfield-effect transistors by design. J Am Chem Soc, 2011, 133: 2605–2612
Dong CG, Hu QS. Preferential oxidative addition in palladium(0)-catalyzed Suzuki cross-coupling reactions of dihaloarenes with arylboronicacids. J Am Chem Soc, 2005, 127: 10006–10007
Yokoyama A, Suzuki H, Kubota Y, Ohuchi K, Higashimura H, Yokozawa T. Chain-growth polymerization for the synthesis ofpolyfluorene via Suzuki-Miyaura coupling reaction from externallyadded initiator unit. J Am Chem Soc, 2007, 129: 7236–7237
Zhang HH, Xing CH, Hu QS, Hong K. Controlled Pd(0)/t-Bu3PcatalyzedSuzuki cross-coupling polymerization of AB-type monomerswith ArPd(t-Bu3P)X or Pd2(dba)3/t-Bu3P/ArX as the initiator. Macromolecules, 2015, 48: 967–978
Azarian D, Dua SS, Eaborn C, Walton DRM. Reactions of organichalides with R3 MMR3 compounds (M=Si,Ge,Sn) in the presence oftetrakis (triarylphosphine) palladium. J Organomet Chem, 1976, 117: C55–C57
Kosugi M, Sasazawa K, Shimizu Y, Migita T. Reactions of allyltincompounds III. Allylation of aromatic halides with allyltributyltin inthe research of tetrakis (triphenylphosphine) palladium(0). Chem Lett, 1977: 301–302
Milstein D, Stille JK. A general, selective, and facile method for ketonesynthesis from acid chlorides and organotin compounds catalyzedby palladium. J Am Chem Soc, 1978, 100: 3636–3638
Carsten B, He F, Son JH, Xu T, Yu L. Stille polycondensation forsynthesis of functional materials. Chem Rev, 2011, 111: 1493–1528
Kranthiraja K, Gunasekar K, Cho W, Song M, Park YG, Lee JY, Shin Y, Kang IN, Kim A, Kim H, Kim BS, Jin SH. Alkoxyphenylthiophenelinked benzodithiophene based medium band gap polymersfor organic photovoltaics: efficiency improvement upon methanoltreatment depends on the planarity of backbone. Macromolecules, 2014, 47: 7060–7069
Qiu Y, Mohin J, Tsai CH, Tristram-Nagle S, Gil RR. Kowalewski T, Noonan KJT. Stille catalyst-transfer polycondensation using Pd-PEPPSI-IPr for high-molecular-weight regioregular poly(3-hexylthiophene). Macromol Rapid Commun, 2015, 36: 840–844
King AO, Okukado N, Negishi E. Highly general stereo-, regio-, andchemo-selective synthesis of terminal and internal conjugated enynesby the Pd-catalysed reaction of alkynylzinc reagents with alkenylhalides. J Chem Soc Chem Commun, 1977: 683–684
Tkachov R, Senkovskyy V, Beryozkina T, Boyko K, Bakulev V, Lederer A, Sahre K, Voit B, Kiriy A. Palladium-catalyzed chain-growthpolycondensation of AB-type monomers: high catalyst turnover andpolymerization rates. Angew Chem Int Ed, 2014, 53: 2402–2407
Mizoroki T, Mori K, Ozaki A. Arylation of olefin with aryl iodidecatalyzed by palladium. Bull Chem Soc Jpn, 1971, 44: 581
Heck RF, Nolley JP. Palladium-catalyzed vinylic hydrogen substitutionreactions with aryl, benzyl, and styryl halides. J Org Chem, 1972, 37: 2320–2322
Beletskaya IP, Cheprakov AV. The Heck reaction as a sharpeningstone of palladium catalysis. Chem Rev, 2000, 100: 3009–3066
Tierze LF, Kettschau G, Heuschert U, Nordmann G. Highly efficientsynthesis of linear pyrrole oligomers by twofold Heck reactions. Chem Eur J, 2001, 7: 368–373
Nicolaou KC, Bulger PG, Sarlah D. Palladium-catalyzed crosscouplingreactions in total synthesis. Angew Chem Int Ed, 2005, 44: 4442–4489
Li J, Jeong S, Esser L, Harran PG. Total synthesis of nominal diazonamides-part 1: convergent preparation of the structure proposed for(-)-diazonamide A. Angew Chem Int Ed, 2001, 40: 4765–4769
Parvez MM, Haraguchi N, Itsuno S. Synthesis of cinchona alkaloidderivedchiral polymers by Mizoroki-Heck polymerization and theirapplication to asymmetric catalysis. Macromolecules, 2014, 47: 1922–1928
Littke AF, Fu GC. A versatile catalyst for Heck reactions of arylchlorides and aryl bromides under mild conditions. J Am Chem Soc, 2001, 123: 6989–7000
Nojima M, Saito R, Ohta Y, Yokozawa T. I nvestigation of Mizoroki-Heck coupling polymerization as a catalyst-transfer condensationpolymerization for synthesis of poly(p-phenylenevinylene). J PolymSci Polym Chem, 2015, 53: 543–551
Sonogashira K, Tohda Y, Hagihara N. A convenient synthesis ofacetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes,iodoarenes and bromopyridines. Tetrahedron Lett, 1975, 16: 4467–4470
Sogawa H, Shiotsuki M, Sanda F. Synthesis and photoresponse ofhelically folded poly(phenyleneethynylene)s bearing azobenzenemoieties in the main chains. Macromolecules, 2013, 46: 4378–4387
Michael A. On the addition of sodium acetacetic ether and analogoussodium compounds to unsaturated organic ethers. Am Chem J, 1887, 9: 115
Mather BD, Viswanathan K, Miller KM, Long TE. Michael additionreactions in macromolecular design for emerging technologies. ProgPolym Sci, 2006, 31: 487–531
Ferrui P. Poly(amidoamine)s: past, present, and perspectives. J PolymSci Polym Chem, 2013, 51: 2319–2353
Cohen S, Coue G, Beno D, Korenstein R, Engbersen JFJ. Bioreduciblepoly(amidoamine)s as carriers for intracellular protein delivery tointestinal cells. Biomaterials, 2012, 33: 614–623
Fang L, Zhang H, Li Z, Zhang Y, Zhang Y, Zhang H. Synthesis ofreactive azobenzene main-chain liquid crystalline polymers via Michaeladdition polymerization and photomechanical effects of theirsupramolecular hydrogen-bonded fibers. Macromolecules, 2013, 46: 7650–7660
Martineau C, Blanchard P, Rondeau D, Delaunay J, Roncali J. Synthesisand electronic properties of adducts of oligothienylenevinylenesand fullerene C60. Adv Mater, 2002, 14: 283–287
Wetering KVD, Brochon C, Ngov C, Hadziioannou G. Design andsynthesis of a low band gap conjugated macroinitiator: toward rodcoildonor-acceptor block copolymers. Macromolecules, 2006, 39: 4289–4297
Intemann JJ, Mike JF, Cai M, Bose S, Xiao T, Mauldin TC, Roggers RA, Shinar J, Shinar R, Jeffries-EL M. Synthesis and characterizationof poly(9,9-dialkylfluorenevinylene benzobisoxazoles): new solutionprocessableelectron-accepting conjugated polymers. Macromolecules, 2011, 44: 248–255
Gandini A. The furan/maleimide Diels-Alder reaction: a versatileclick-unclick tool in macromolecular synthesis. Prog Polym Sci, 2013,38: 1–29
Satoh H, Mineshima A, Nakamura T, Teramoto N, Shibata M. Thermo-reversible Diels-Alder polymerization of difurfurylidene diglyceroland bismaleimide. React Funct Polym, 2014, 76: 49–56
Chen Z, Amara JP, Thomas SW, Swager TM. Synthesis of a novelpoly(iptycene) ladder polymer. Macromolecules, 2006, 39: 3202–3209
Dibble DJ, Umerani MJ, Mazaheripour A, Park YS, Ziller JW, Gorodetsky AA. An aza-Diels-Alder route to polyquinolines. Macromolecules, 2015, 48: 557–561
Ji S, Bruchmann B, Klok HA. Synthesis of side-chain functionalpolyesters via Baylis-Hillman polymerization. Macromolecules, 2011,44: 5218–5226
Jones RR, Bergman RG. p-Benzyne. Generation as an intermediate ina thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure. J Am Chem Soc, 1972, 94: 660–661
Kar M, Basak A. Design, synthesis, and biological activity ofunnatural enediynes and related analogues equipped with pHdependentor phototriggering Devices. Chem Rev, 2007, 107: 2861–2890
John JA, Tour JM. Synthesis of polyphenylenes and polynaphthalenesby thermolysis of enediynes and dialkynylbenzenes. J AmChem Soc, 1994, 116: 5011–5012
Xiao Y, Hu A. Bergman cyclization in polymer chemistry and materialscience. Macromol Rapid Commun, 2011, 32: 1688–1698
Cheng X, Ma J, Zhi J, Yang X, Hu A. Synthesis of novel “Rod-Coil”brush polymers with conjugated backbones through Bergmancyclization. Macromolecules, 2010, 43: 909–913
Ma J, Ma X, Deng S, Li F, Hu A. Synthesis of dendronized polymersthrough Bergman cyclization of enediyne-containing Frechet-typedendrimers. J Polym Sci Polym Chem, 2011, 49: 1368–1375
Sun S, Zhu C, Song D, Li F, Hu A. Preparation of conjugated polyphenylenesfrom maleimide-based enediynes through thermaltriggeredBergman cyclization polymerization. Polym Chem, 2014, 5: 1241–1247
Miao C, Zhi J, Sun S, Yang X, Hu A. Formation of conjugated polynaphthalenevia Bergman cyclization. J Polym Sci Polym Chem, 2010, 48: 2187–2193
Sun Q, Zhang C, Li Z, Kong H, Tan Q, Hu A, Xu W. On-surfaceformation of one-dimensional polyphenylene through Bergman cyclization. J Am Chem Soc, 2013, 135: 8448–8451
Zhu J, Bienaymé H. Multicomponent Reactions. Weinheim: Wiley-VCH, 2005
Brauch S, van Berkel SS, Westermann B. Higher-order multicomponentreactions: beyond four reactants. Chem Soc Rev, 2013, 42: 4948–4962
Zhu C, Yang B, Zhao Y, Fu C, Tao L, Wei Y. A new insight into theBiginelli reaction: the dawn of multicomponent click chemistry. Polym Chem, 2013, 4: 5395–5400
Zhang Y, Zhao Y, Yang B, Zhu C, Wei Y, Tao L. “ One pot” synthe sis of well-defined poly(aminophosphonate)s: time for the Kabachnik-Fields reaction on the stage of polymer chemistry. Polym Chem, 2014, 5: 1857–1862
Zhang Q, Zhang Y, Zhao Y, Yang B, Fu C, Wei Y, Tao L. Multicomponentpolymerization system combining Hantzsch reaction andreversible addition-fragmentation chain transfer to efficiently synthesizewell-defined poly(1,4-dihydropyridine)s. ACS Macro Lett, 2015,4: 128–132
Kakuchi P. Multicomponent reactions in polymer synthesis. AngewChem Int Ed, 2014, 53: 46–48
Passerini M. Isonitriles. II. Compounds with aldehydes or with ketonesand monobasic organic acids. Gazz Chem Ital, 1921, 51: 181–189
Kreye O, Tóth T, Meier MAR. Introducing multicomponent reactionsto polymer science: Passerini reactions of renewable monomers. J AmChem Soc, 2011, 133: 1790–1792
Deng XX, Li L, Li ZL, Lv A, Du FS, Li ZC. Sequence regulatedpoly(ester-amide)s based on Passerini reaction. ACS Macro Lett, 2012, 1: 1300–1303
Wang YZ, Deng XX, Li L, Li ZL, Du FS, Li ZC. One-pot synthesisof polyamides with various functional side groups via Passerini reaction. Polym Chem, 2013, 4: 444–448
Li L, Deng XX, Li ZL, Du FS, Li ZC. Multifunctional photodegradablepolymers for reactive micropatterns. Macromolecules, 2014, 47: 4660–4667
Zhang LJ, Deng XX, F Du FS, Li ZC. Chemical synthesis of functionalpoly(4-hydroxybutyrate) with controlled degradation via intramolecularcyclization. Macromolecules, 2013, 46: 9554–9562
Kreye O, Türünç O, Sehlinger A, Rackwitz J, Meier MAR. Structurallydiverse polyamides obtained from monomers derived via the Ugimulticomponent reaction. Chem Eur J, 2012, 18: 5767–5776
Sehlinger A, Dannecker PK, Kreye O, and Meier MAR. Diverselysubstituted polyamides: macromolecular design using the Ugifour-component reaction. Macromolecules, 2014, 47: 2774–2783
Sehlinger A, Schneider R, Meier MAR. Ugi reactions with CO2: accessto functionalized polyurethanes, polycarbonates, polyamides,and polyhydantoins. Macromol Rapid Commun, 2014, 35: 1866–1871
Hulme C, Ma L, Romano JJ, Morton G, Tang SY, Cherrier MP, Choi S, Salvino J, Labaudiniere R. Novel application of carbon dioxide/MeOH for synthesis of hydantoins and cyclic ureas via the Ugi reaction. Tetrahedron Lett, 2000, 41: 1889–1893
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Jiang, X., Feng, C., Lu, G. et al. Application of named reactions in polymer synthesis. Sci. China Chem. 58, 1695–1709 (2015). https://doi.org/10.1007/s11426-015-5447-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-015-5447-1