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CC BY 4.0 · SynOpen 2023; 07(04): 580-614
DOI: 10.1055/s-0040-1720096
DOI: 10.1055/s-0040-1720096
review
A Decade of Exploration of Transition-Metal-Catalyzed Cross-Coupling Reactions: An Overview
S.K. is thankful to Council of Scientific and Industrial Research (CSIR) for his fellowship.
Abstract
During the previous couple of decades, transition-metal (Fe, Co, Cu, Ni, Ru, Rh, Pd, Ag, Au) catalyzed inter- and intramolecular coupling reactions have attracted huge attention for the construction of C–C and C–heteroatom (like C–N, C–P, C–O, C–S, etc.) bonds to synthesize a diverse range of polymers, fine chemicals, and agrochemicals (mainly fungicides, herbicides, and insecticides), as well as biologically and pharmaceutically important organic molecules. Furthermore, the employment of lower cost and easily available metals such as first-row transition-metal salts or metal complexes of Fe, Co, Cu, Ni as catalysts compared to the precious metals such as Pd, Ag, Au in cross-coupling reactions have led to major advances in applications within the fields of synthesis. A number of cross-coupling reactions catalyzed by transition metals have been explored, including Suzuki, Heck, Sonogashira, Stille, Kumada, Kochi, Murahashi, Corriu, and Negishi reactions, as well as carbonylative, decarboxylative, reactions and α-arylations. In this review, we offer a comprehensive summary of the cross-coupling reaction catalyzed by different transition metals from the year 2009 to date.
1 Introduction
2 Pd-Catalyzed Reactions
2.1 C–C Cross-Coupling Reactions
2.2 C–N Cross-Coupling Reactions
2.3 C–P Cross-Coupling Reactions
3 Ni-Catalyzed Cross-Coupling Reactions
3.1 C–C Cross-Coupling Reactions
4 Cu-Catalyzed Cross-Coupling Reactions
4.1 C–C Cross-Coupling Reactions
4.2 C–O Cross-Coupling Reactions
4.2 C–N Cross-Coupling Reactions
4.4 C–P Cross-Coupling Reactions
4.5 C–Se Cross-Coupling Reactions
4.6 C–S Cross-Coupling Reactions
5 Fe-Catalyzed Reactions
5.1 C–C Cross-Coupling Reactions
5.2 C–S Cross-Coupling Reactions
6 Co-Catalyzed Reactions
7 Transition-Metal Nanoparticle-Promoted Reactions
7.1 Pd Nanoparticles
7.2 Cu Nanoparticles
8 Miscellaneous Reactions
9 Perspectives and Future Directions
Publication History
Received: 01 August 2023
Accepted after revision: 21 September 2023
Article published online:
13 November 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 2 Heck RF. Org. React. 1982; 27: 345
- 3 Sonogashira K. In Comprehensive Organic Synthesis, Vol. 3. Trost BM, Fleming I. Pergamon; Oxford: 1991: 521
- 4a Milstein D, Stille JK. J. Am. Chem. Soc. 1979; 101: 4981
- 4b Milstein D, Stille JK. J. Am. Chem. Soc. 1979; 101: 4992
- 4c Milstein D, Stille JK. J. Org. Chem. 1979; 44: 1613
- 5a Negishi E. Acc. Chem. Res. 1982; 15: 340
- 5b Erdik E. Tetrahedron 1992; 48: 9577
- 5c Negishi EI, Liu F. In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 1-47
- 6 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
- 7 Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
- 8 Schlummer B, Scholz U. Adv. Synth. Catal. 2004; 346: 1599
- 9 Beletskaya IP, Ananikov VP. Chem. Rev. 2011; 111: 1596
- 10 Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
- 11 Zweig JE, Kim DE, Newhouse TR. Chem. Rev. 2017; 117: 11680
- 12 Torborg C, Beller M. Adv. Synth. Catal. 2009; 351: 3027
- 13 Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
- 14 Bao Z, Chen Y, Cai R, Yu L. Macromolecules 1993; 26: 5281
- 15 Yang S.-H, Hsu C.-S. J. Polym. Sci., Part A: Polym. Chem. 2009; 47: 2713
- 16 Chang N.-H, Kinoshita M, Nishihara Y. Liquid Crystals . In Applied Cross-Coupling Reactions . Nishihara Y. Lecture Notes in Chemistry; Springer; Berlin: 2013: 111-135
- 17 Naso F, Babudri F, Farinola GM. Pure Appl. Chem. 1999; 71: 1485
- 18 Figueira-Duarte TM, Müllen K. Chem. Rev. 2011; 111: 7260
- 19 Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 34: 2174
- 20 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
- 21 Corriu RJ. P, Masse JP. J. Chem. Soc., Chem. Commun. 1972; 144a
- 22 Heck RF. Palladium-Catalyzed Vinylation of Organic Halides. In Organic Reactions. John Wiley & Sons Inc; Hoboken: 1982: 345-390
- 23 Mizoroki T, Mori K, Ozaki A. Bull. Chem. Soc. Jpn. 1971; 44: 581
- 24 Heck RF, Nolley JP. J. Org. Chem. 1972; 37: 2320
- 25 Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 4467
- 26 Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N. Synthesis 1980; 627
- 27 Baba S, Negishi E. J. Am. Chem. Soc. 1976; 98: 6729
- 28 Negishi E. Acc. Chem. Res. 1982; 15: 340
- 29 Milstein D, Stille JK. J. Am. Chem. Soc. 1978; 100: 3636
- 30 Milstein D, Stille JK. J. Am. Chem. Soc. 1979; 101: 4992
- 31 Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 3437
- 32 Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 33 Miyaura N, Yanagi T, Suzuki A. Synth. Commun. 1981; 11: 513
- 34 Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
- 35 Hatanaka Y, Hiyama T. J. Org. Chem. 1988; 53: 918
- 36 Hiyama T. J. Organomet. Chem. 2002; 653: 58
- 37 Old DW, Wolfe JP, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 9722
- 38 Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
- 39 Kohei T, Miyaura N. Introduction to Cross-Coupling Reactions. In Cross-Coupling Reactions. Miyaura N. Topics in Current Chemistry, Vol. 219; Springer; Berlin: 2002: 1-9
- 40 Negishi EJ. Organomet. Chem. 2002; 653: 34
- 41 Seechurn JC. C. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 42 Suzuki A., Heck R. F., Negishi E., The Nobel Prize in Chemistry, 2010 (accessed Feb15, 2018): http://image.sciencenet.cn/olddata/kexue.com.cn/upload/blog/file/2010/10/2010106224251568280.pd
- 43 Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
- 44 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 45 Wu X.-F, Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
- 46 Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 47 Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
- 48 Schlummer B, Scholz U. Adv. Synth. Catal. 2004; 346: 1599
- 49 Czaplik W. M., Mayer M., Cvengros J., von Wangelin A. J. 2009, 2: 396
- 50 Fürstner A, Leitner A, Mendez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
- 51 Piontek A, Bisz E, Szostak M. Angew. Chem. Int. Ed. 2018; 57: 11116
- 52 Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
- 53 Li B, Wu Z.-H, Gu Y.-F, Sun C.-L, Wang B.-Q, Shi Z.-J. Angew. Chem. 2011; 123: 1141
- 54 Gensch T, Klauck FJ. R, Glorius F. Angew. Chem. Int. Ed. 2016; 55: 11287
- 55 Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435
- 56 Gosmini C, Moncomble A. Isr. J. Chem. 2010; 50: 568
- 57 Netherton MR, Fu GC. Adv. Synth. Catal. 2004; 346: 1525
- 58 Wang Q, Chen C. Tetrahedron Lett. 2008; 49: 2916
- 59 Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
- 60 Phapale VB, Cardenas DJ. Chem. Soc. Rev. 2009; 38: 1598
- 61 Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
- 62 Thapa S, Shrestha B, Gurung SK, Giri R. Org. Biomol. Chem. 2015; 13: 4816
- 63 Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
- 64 Yang C.-T, Zhang Z.-Q, Liu Y.-C, Liu L. Angew. Chem. 2011; 123: 3990
- 65 Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
- 66 Modern Rhodium-Catalyzed Organic Reactions . Evans PA. Wiley-VCH Verlag GmbH; Weinheim: 2005
- 67 Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
- 68 Kuhl N, Schröder N, Glorius F. Adv. Synth. Catal. 2014; 356: 1443
- 69 Lautens M, Roy A, Fukuoka K, Fagnou K, Martín-Matute B. J. Am. Chem. Soc. 2001; 123: 5358
- 70 Farrington EJ, Brown JM, Barnard CF. J, Rowsell E. Angew. Chem. Int. Ed. 2002; 41: 169
- 71 Oi S, Aizawa E, Ogino Y, Inoue Y. J. Org. Chem. 2005; 70: 3113
- 72 Koike T, Du X, Sanada T, Danda Y, Mori A. Angew. Chem. Int. Ed. 2003; 42: 89
- 73 Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
- 74 Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
- 75 Miao J, Ge H. Eur. J. Org. Chem. 2015; 7859
- 76 Balasubramanian M. Industrial Scale Palladium Chemistry . In Palladium in Heterocyclic Chemistry, Vol. 26. Li JJ, Gribble GW. Elsevier; Amsterdam: 2007: 587-620
- 77 Torborg C, Beller M. Adv. Synth. Catal. 2009; 351: 3027
- 78a Yu D.-G, Li B.-J, Shi Z.-J. Acc. Chem. Res. 2010; 43: 1486
- 78b Mesganaw T, Garg NK. Org. Process Res. Dev. 2013; 17: 29
- 79a Zhao Y.-L, Wu G.-J, Han F.-S. Chem. Commun. 2012; 48: 5868
- 79b Zhao Y.-L, Wu G.-J, Li Y, Gao L.-X, Han F.-S. Chem. Eur. J. 2012; 18: 9622
- 80a Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
- 80b Li B.-J, Yu D.-G, Sun C.-L, Shi Z.-J. Chem. Eur. J. 2011; 17: 1728
- 81a Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
- 81b Shinokubo H, Oshima K. Eur. J. Org. Chem. 2004; 2071
- 81c Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
- 81d Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
- 81e Cahiez G, Duplais C. The Chemistry of Organomagnesium Compounds . Wiley VCH; Weinheim: 2008
- 81f Plietker B. Iron Catalysis in Organic Synthesis . Wiley-VCH; Weinheim: 2008
- 81g Correa A, Mancheno OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
- 81h Czaplik WM, Mayer M, Cvengros J, von Wangelin AJ. ChemSusChem 2009; 2: 396
- 81i Sun C.-L, Li B.-J, Shi Z.-J. Chem. Rev. 2011; 111: 1293
- 81j Nakamura E, Hatakeyama T, Ito S, Ishizuka K, Ilies L, Nakamura M. Org. React. 2014; 83: 1
- 82a Bauer E. Iron Catalysis II . Springer International Publishing; Switzerland: 2015
- 82b Plietker B. Iron Catalysis in Organic Chemistry: Reactions and Applications. Wiley-VCH; New York: 2008
- 82c Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
- 82d Kuzmina OM, Steib AK, Moyeux A, Cahiez G, Knochel P. Synthesis 2015; 1696
- 82e Bedford RB, Brenner PB. Top. Organomet. Chem. 2015; 50: 19
- 82f Bauer I, Knölker H.-J. Chem. Rev. 2015; 115: 3170
- 82g Gopalaiah K. Chem. Rev. 2013; 113: 3248
- 83 Kharasch MS, Fields EK. J. Am. Chem. Soc. 1941; 63: 2316
- 84a Tamura M, Kochi JK. J. Am. Chem. Soc. 1971; 93: 1487
- 84b Tamura M, Kochi JK. Synthesis 1971; 303
- 84c Kwan CL, Kochi JK. J. Am. Chem. Soc. 1976; 98: 4903
- 84d Smith RS, Kochi JK. J. Org. Chem. 1976; 41: 502
- 85 Fabre J.-L, Julia M, Verpeaux J.-N. Tetrahedron Lett. 1982; 23: 2469
- 86 Molander GA, Rahn BJ, Shubert DC, Bonde SE. Tetrahedron Lett. 1983; 24: 5449
- 87a Cahiez G, Marquais S. Pure Appl. Chem. 1996; 68: 53
- 87b Cahiez G, Marquais S. Tetrahedron Lett. 1996; 37: 1773
- 87c Cahiez G, Avedissian H. Synthesis 1998; 1199
- 87d Dohle W, Kopp F, Cahiez G, Knochel P. Synlett 2001; 1901
- 88a Fürstner A, Leitner A, Mendez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
- 88b Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2002; 41: 609
- 88c Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2003; 42: 308
- 88d Martin R, Fürstner A. Angew. Chem. Int. Ed. 2004; 43: 3955
- 89 Nagano T, Hayashi T. Org. Lett. 2004; 6: 1297
- 90 Nakamura M, Matsuo K, Ito S, Nakamura E. J. Am. Chem. Soc. 2004; 126: 3686
- 91 Itami K, Higashi S, Mineno M, Yoshida J.-i. Org. Lett. 2005; 7: 1219
- 92a Bedford RB, Bruce DW, Frost RM, Goodby JW, Hird M. Chem. Commun. 2004; 2822
- 92b Bedford RB, Bruce DW, Frost RM, Hird M. Chem. Commun. 2005; 4161
- 92c Bedford RB, Betham M, Bruce DW, Danopoulos AA, Frost RM, Hird M. J. Org. Chem. 2006; 71: 1104
- 93 Dunet G, Knochel P. Synlett 2006; 407
- 94 Li B.-J, Xu L, Wu Z.-H, Guan B.-T, Sun C.-L, Wang B.-Q, Shi Z.-J. J. Am. Chem. Soc. 2009; 131: 14656
- 95 Bouissane L, Sestelo JP, Sarandeses LA. Org. Lett. 2009; 6: 1285
- 96 Raju J, Vance R, Goodman JA, Reeder AJ, Liao MR, Maust J, Irish MT, Espino PA, Andrews PD. R. Org. Lett. 2009; 11: 1463
- 97 Cai M, Zheng G, Ding G. Green Chem. 2009; 11: 1687
- 98 Basu B, Biswas K, Kundu S, Ghosh S. Green Chem. 2010; 12: 1734
- 99 Lee D.-H, Jung J.-Y, Jin M.-J. Green Chem. 2010; 12: 2024
- 100 Milton EJ, Clarke ML. Green Chem. 2010; 12: 381
- 101 Peng Y.-Y, Liu J, Lei X, Yin Z. Green Chem. 2010; 12: 1072
- 102 Marziale AN, Faul SH, Reiner T, Schneider S, Eppinger J. Green Chem. 2010; 12: 35
- 103 Long B, Yang Y, Wang L, He W, Xiang J. Synth. Commun. 2010; 40: 1202
- 104 Chen Y, Cao W, Wu K, Chen J, Lee AW. M. Synth. Commun. 2010; 40: 984
- 105 Molander GA, Hiebel M.-A. Org. Lett. 2010; 2: 4876
- 106 Liu C, Ni Q, Bao F, Qiu J. Green Chem. 2011; 13: 1260
- 107 Islam M, Mondal P, Roy AS, Tuhina K, Mondal S, Hossain D. Synth. Commun. 2011; 41: 2583
- 108 Lee PH, Mo J, Kang D, Eom D, Park C, Lee C.-H, Jung YM, Hwang H. J. Org. Chem. 2011; 76: 312
- 109 Ali H, Ait-Mohand S, Gosselin S, van Lier JE, Guerin B. J. Org. Chem. 2011; 76: 1887
- 110 Modak A, Mondal J, Sasidharan M, Bhaumik A. Green Chem. 2011; 13: 1317
- 111 Modak A, Mondal J, Bhaumik A. Green Chem. 2012; 14: 2840
- 112 Susanto W, Chu C.-Y, Ang WJ, Chou T.-C, Lo L.-C, Lam Y. Green Chem. 2012; 14: 77
- 113 Mondal M, Bora U. Green Chem. 2012; 14: 1873
- 114 Wang L, Welker ME. J. Org. Chem. 2012; 77: 8280
- 115 Liu C, Zhang Y, Liu N, Qiu J. Green Chem. 2012; 14: 2999
- 116 Keller M, Hameau A, Spataro G, Ladeira S, Caminade A.-M, Majoral J.-P, Ouali A. Green Chem. 2012; 14: 2807
- 117 Saha P, Mondal S, Hazra A, Naskar S, Maity A, Sahu KB, Paira R, Das S, Banerjee S, Mondal NB. Synth. Commun. 2012; 42: 3166
- 118 Lu G.-P, Caib C, Lipshutz BH. Green Chem. 2013; 15: 105
- 119 Oberholzera M, Frech CM. Green Chem. 2013; 15: 1678
- 120 Yang J, Wang D, Liu W, Zhang X, Bian F, Yu W. Green Chem. 2013; 15: 3429
- 121 Ding G, Wang W, Jiang T, Han B. Green Chem. 2013; 15: 3396
- 122 Yan H, Sun P, Qu X, Lu L, Zhu Y, Yang H, Mao J. Synth. Commun. 2013; 43: 2773
- 123 Zhang G, Luan Y, Han X, Wang Y, Wen X, Ding C, Gao J. Green Chem. 2013; 15: 2081
- 124 Yuan H, Shen Y, Yu S, Shan L, Sun Q, Zhang W. Synth. Commun. 2013; 43: 2817
- 125 Cheng K, Hu S, Zhao B, Zhang X.-M, Qi C. J. Org. Chem. 2013; 78: 5022
- 126 Sakashita S, Takizawa M, Sugai J, Ito H, Yamamoto Y. Org. Lett. 2013; 15: 4308
- 127 Ojha DP, Prabhu KR. J. Org. Chem. 2013; 78: 12136
- 128 Liu L, Dong Y, Tang N. Green Chem. 2014; 16: 2185
- 129 Zhao H, Cheng M, Zhang J, Cai M. Green Chem. 2014; 16: 2515
- 130 Nehra P, Khungar B, Pericherla K, Sivasubramanian SC, Kumar A. Green Chem. 2014; 16: 4266
- 131 Li L, Zhao S, Joshi-Pangu A, Diane M, Biscoe MR. J. Am. Chem. Soc. 2014; 136: 14027
- 132 Nadaf RN, Seapy DG. Synth. Commun. 2014; 44: 2012
- 133 Strueben J, Gates PJ, Staubitz A. J. Org. Chem. 2014; 79: 1719
- 134 Sun F, Lv L, Huang M, Zhou Z, Fang X. Org. Lett. 2014; 16: 5024
- 135 Tan J, Chen Y, Li H, Yasuda N. J. Org. Chem. 2014; 79: 8871
- 136 Shen C, Shen H, Yang M, Xia C, Zhang P. Green Chem. 2015; 17: 225
- 137 da Silva JF. M, Perez AF. Y, de Almeida NP. Synth. Commun. 2015; 17: 1995
- 138 Boruah PR, Ali AA, Saikia B, Sarma D. Green Chem. 2015; 17: 1442
- 139 Strappaveccia G, Ismalaj E, Petrucci C, Lanari D, Marrocchi A, Drees M, Facchetti A, Vaccaro L. Green Chem. 2015; 17: 365
- 140 Strappaveccia G, Luciani L, Bartollini E, Marrocchi A, Pizzo F, Vaccaro L. Green Chem. 2015; 17: 1071
- 141 Khana RI, Pitchumani K. Green Chem. 2016; 18: 5518
- 142 Jadhav SN, Kumbhar AS, Rode CV, Salunkhe RS. Green Chem. 2016; 18: 1898
- 143 Wang J, Zong Y, Wang X, Hu Y, Yuea G, Pan Y. Green Chem. 2016; 18: 967
- 144 Nambo M, Keske EC, Rygus JP. G, Yim JC.-H, Crudden CM. Green Chem. 2017; 7: 1108
- 145 Pulipati Y, Gurram V, Laxmi SV, Satyanarayana Y, Singh K, Kumar V, Sharma S, Pottabathini N, Iska VB. R. Synth. Commun. 2017; 12: 1142
- 146 Chen X, Zhou X.-Y, Wang L.-G. Synth. Commun. 2017; 22: 2096
- 147 Jadhav SN, Rode CV. Green Chem. 2017; 19: 5958
- 148 Clavé G, Pelissier F, Campidellib S, Grison C. Green Chem. 2017; 19: 4093
- 149 Markovic T, Murray PR. D, Rocke BN, Shavnya A, Blakemore DC, Willism MC. J. Am. Chem. Soc. 2018; 140: 15916
- 150 Sharma S, Sarkar BR. Synth. Commun. 2018; 8: 906
- 151 Landstrom EB, Handa S, Aue DH, Gallou F, Lipshutz BH. Green Chem. 2018; 20: 3436
- 152 Gong X, Wu J, Meng Y, Zhang Y, Ye L.-W, Zhu C. Green Chem. 2019; 21: 995
- 153 Chehrouri M, Othman AA, Jiménez-Cecilia S, Cabrerizo CM, Sansano JM. Synth. Commun. 2019; 10: 1301
- 154 Balfour MN, Zukerman-Schpector J, Rodriguez MJ. D, Reis JS, Esteves CH. A, Stefani HA. Synth. Commun. 2019; 3: 351
- 155 Liu X, Xu W, Xiang D, Zhang Z, Chen D, Hu Y, Li Y, Ouyang Y, Lin H. New J. Chem. 2019; 43: 12206
- 156 Zhou Z, Li J, Xu Z, Cai M. Synth. Commun. 2020; 13: 2015
- 157 Bangar PG, Nahide PD, Meroliya HK, Waghmode SA, Iyer S. Synth. Commun. 2021; 2: 308
- 158 Fors BP, Buchwald SL. J. Am. Chem. Soc. 2010; 45: 15914
- 159 Dooleweerdt K, Fors BP, Buchwald SL. Org. Lett. 2010; 10: 2350
- 160 Perez F, Minatti A. Org. Lett. 2011; 8: 1984
- 161 Tambade PJ, Patil YP, Qureshi ZS, Dhake KP, Bhanage BM. Synth. Commun. 2012; 1: 176
- 162 Zhang G, Wang X, Li C, Yin D. Synth. Commun. 2013; 43: 456
- 163 Wagner P, Bollenbach M, Doebelin C, Bihel F, Bourguignon J.-J, Salomé C, Schmitt M. Green Chem. 2014; 16: 4170
- 164 Fan A, Peng J, Zhou D, Li X, Chen C. Synth. Commun. 2020; 20: 3113
- 165 Feng T, Luo X, Dong J, Mo J. Synth. Commun. 2021; 51 (08) 1284
- 166 Patel JJ, Patel AP, Chikhalia KH. Synth. Commun. 2021; 1: 81
- 167 Xu K, Yang F, Zhang G, Wu Y. Green Chem. 2013; 15: 1055
- 168 Hayashi M, Matsuura T, Tanaka I, Ohta H, Watanabe Y. Org. Lett. 2013; 13: 628
- 169 Taylor BL. H, Jarvo ER. J. Org. Chem. 2011; 76: 7573
- 170 Liu H, Liang Z, Qian Q, Lin K. Synth. Commun. 2014; 20: 2999
- 171 Tollefson EJ, Dawson DD, Osborne CA, Jarvo ER. J. Am. Chem. Soc. 2014; 136: 14951
- 172 Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344
- 173 Dawson DD, Jarvo ER. Org. Process Res. Dev. 2015; 19: 1356
- 174 Funicello M, Chiummiento L, Lupattelli P, Tramutola F. Synth. Commun. 2015; 15: 1799
- 175 Liao Y, Yang W, Wei T, Cai M. Synth. Commun. 2019; 9: 1134
- 176 Yalavarty M, Paradise CM, Klein TA. L, Miles DH. Synth. Commun. 2010; 11: 1625
- 177 Chen G, Xie J, Weng J, Zhu X, Zheng Z, Cai J, Wan Y. Synth. Commun. 2011; 21: 3123
- 178 Wang B, Zhu J, Wei Y, Luo G, Qu H, Liu LX. Synth. Commun. 2015; 24: 2841
- 179 Sagadevan A, Lyub P.-C, Hwang KC. Green Chem. 2016; 18: 4526
- 180 Ali I, Nighot D, Lone MN, Jain A. Synth. Commun. 2017; 12: 1175
- 181 Charpe VP, Hande AA, Sagadevan A, Hwang KC. Green Chem. 2018; 20: 4859
- 182 Xu H, Wu K, Tian J, Zhu L, Yao X. Green Chem. 2018; 20: 793
- 183 Liao M, Zhang X, Yue P. Synth. Commun. 2018; 13: 1694
- 184 Baig RB. N, Vaddula BR, Nadagouda MN, Varma RS. Green Chem. 2015; 17: 1243
- 185 Zhang J, Chen J, Liu M, Zheng X, Ding J, Wu H. Green Chem. 2012; 14: 912
- 186 Xiong W, Qi C, Guo T, Zhang M, Chena K, Jiang H. Green Chem. 2017; 19: 1642
- 187 Saranya TV, Sruthi PR, Anas S. Synth. Commun. 2019; 2: 297
- 188 Chen J, Wang J, Chen X, Huang Y, Shouzhi P. Synth. Commun. 2019; 6: 836
- 189 Wang F.-H, Liu Z.-Y, Yang S, Shi L, Lin D.-Z, Liu H.-Y, Yuan G.-Q. Synth. Commun. 2021; 13: 2053
- 190 Li X, Yang D, Jiang Y, Fu H. Green Chem. 2010; 12: 1097
- 191 Liu Z.-J, Vors J.-P, Gesing ER. F, Bolm C. Green Chem. 2011; 13: 42
- 192 Cao C, Lu Z, Cai Z, Pang G, Shi Y. Synth. Commun. 2012; 2: 279
- 193 Sagadevan A, Ragupathi A, Lin C.-C, Hwu JR, Hwang KC. Green Chem. 2015; 17: 1113
- 194 Wang X, Wang M, Xie J. Synth. Commun. 2017; 19: 1797
- 195 Bai D.-X, Lim RS.-E, Ng H.-F, Teo Y.-C. Synth. Commun. 2021; 9: 1398
- 196 Chen W, Ma D, Hu G, Hong Z, Gao Y, Zhao Y. Synth. Commun. 2016; 14: 1175
- 197 Ricordi VG, Freitas CS, Perin G, Lenardão EJ, Jacob RG, Savegnago L, Alves D. Green Chem. 2012; 14: 1030
- 198 Yang Y, Dong W, Guo Y, Rioux RM. Green Chem. 2013; 15: 3170
- 199 Shen C, Xu J, Yu W, Zhang P. Green Chem. 2014; 16: 3007
- 200 Yu S, Liu Y, Wang J, Luo F, Cheng H, Jiang Y. Synth. Commun. 2018; 19: 2566
- 201 Chen J, Zhang K, Zhao Y, Pu S. Synth. Commun. 2018; 11: 1316
- 202 Ghodsinia SS. E, Akhlaghinia B. Green Chem. 2019; 21: 3029
- 203 Ning Z, Xu Z, Liu R, Du Z. Synth. Commun. 2021; 51: 3492
- 204 Colacino E, Benakki H, Guenoun F, Martinez J, Lamaty F. Synth. Commun. 2009; 9: 1583
- 205 Liu S, Chen R, Guo X, Yang H, Deng G, Li C.-J. Green Chem. 2012; 14: 1577
- 206 Adams CJ, Bedford RB, Carter E, Gower NJ, Haddow MF, Harvey JN, Huwe M, Cartes MÁ, Mansell SM, Mendoza C, Murphy DM, Neeve EC, Nunn J. J. Am. Chem. Soc. 2012; 134: 10333
- 207 Yang J, Shen G, Chen D. Synth. Commun. 2013; 6: 837
- 208 Agrawal T, Cook SP. Org. Lett. 2013; 1: 96
- 209 Hajipour AR, Azizi G. Green Chem. 2013; 15: 1030
- 210 Bisz E, Szostak M. Green Chem. 2017; 19: 5361
- 211 Crockett MP, Tyrol CC, Wong AS, Li B, Byers JA. Org. Lett. 2018; 20: 5233
- 212 Wu W.-Y, Wang J.-C, Tsai F.-Y. Green Chem. 2009; 11: 326
- 213 Duong HA, Wu W, Teo Y.-Y. Organometallics 2017; 36: 4363
- 214 Prastaro A, Ceci P, Chiancone E, Boffi A, Cirilli R, Colone M, Fabrizi G, Stringaroe A, Cacchi S. Green Chem. 2009; 11: 1929
- 215 Søbjerg LS, Gauthier D, Lindhardt AT, Bunge M, Finster K, Meyer RL, Skrydstrup T. Green Chem. 2009; 11: 2041
- 216 Zhou C, Wang J, Li L, Wang R, Hong M. Green Chem. 2011; 13: 2100
- 217 Khalafi-Nezhad A, Panahi F. Green Chem. 2011; 13: 2408
- 218 Bej A, Srimani D, Sarkar A. Green Chem. 2012; 14: 661
- 219 Cacchi S, Caponetti E, Casadei MA, Giulio AD, Fabrizi G, Forte G, Goggiamani A, Moreno S, Paolicelli P, Petrucci F, Prastaroa A, Saladino ML. Green Chem. 2012; 14: 317
- 220 Huang S.-H, Liua C.-H, Yang C.-M. Green Chem. 2014; 16: 2706
- 221 Puthiaraja P, Pitchumani K. Green Chem. 2014; 16: 4223
- 222 Mandegani Z, Asadi M, Asadi Z, Mohajeri A, Iranpoor N, Omidvar A. Green Chem. 2015; 17: 3326
- 223 Gautam P, Dhiman M, Polshettiwar V, Bhanage BM. Green Chem. 2016; 18: 5890
- 224 Yamada M, Shio Y, Akiyama T, Honma T, Ohki Y, Takahashi N, Murai K, Arisawa M. Green Chem. 2019; 21: 4541
- 225 Mohazzab BF, Jaleh B, Issaabadi Z, Nasrollahzadeh M, Varma RS. Green Chem. 2019; 21: 3319
- 226 Dhara K, Parasar B, Patil AJ, Dash J. Synth. Commun. 2019; 6: 859
- 227 Blanco M, Mosconi D, Tubaro C, Biffis A, Badocco D, Pastore P, Otyepka M, Bakandritsos A, Liu Z, Ren W, Agnoli S, Granozzi G. Green Chem. 2019; 21: 5238
- 228 Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T. J. Org. Chem. 2009; 74: 1971
- 229 Sun W, Wang Y, Wu X, Yao X. Green Chem. 2013; 15: 2356
- 230 Wang K, Yang L, Zhao W, Cao L, Sun Z, Zhang F. Green Chem. 2017; 19: 1949
- 231 Guo D, Huang H, Zhou Y, Xu J, Jiang H, Chena K, Liu H. Green Chem. 2010; 12: 276
- 232 Vaddula BR, Saha A, Leazer J, Varma RS. Green Chem. 2012; 14: 2133
- 233 Al-Amin M, Akimoto M, Tameno T, Ohki Y, Takahashi N, Hoshiya N, Shutoa S, Arisawa M. Green Chem. 2013; 15: 1142
- 234 Akiyama T, Taniguchi T, Saito N, Doi R, Honma T, Tamenori Y, Ohki Y, Takahashi N, Fujioka H, Sato Y, Arisawa M. Green Chem. 2017; 19: 3357
- 235 Zolfigol MA, Khakyzadeh V, Moosavi-Zare AR, Rostami A, Zare A, Iranpoor N, Beyzavie MH, Luque R. Green Chem. 2013; 15: 2132
- 236 Steib AK, Kuzmina OM, Fernandez S, Flubacher D, Knochel P. J. Am. Chem. Soc. 2013; 135: 15346
- 237 Karimi B, Mansouria F, Valib H. Green Chem. 2014; 16: 2587
- 238 Baig RB. N, Nadagouda MN, Varma RS. Green Chem. 2014; 19: 4333
- 239 Rathi AK, Gawande MB, Pechousek J, Tucek J, Aparicio C, Petr M, Tomanec O, Krikavova R, Travnicek Z, Varma RS, Zboril R. Green Chem. 2016; 18: 2363
- 240 Mohammadinezhad A, Akhlaghinia B. Green Chem. 2017; 19: 5625
- 241 Kaur N, Kaur G, Bhalla A, Dhaub JS, Chaudhary GR. Green Chem. 2018; 20: 1506
- 242 Kazemnejadi M, Alavi SA, Rezazadeh Z, Nasseri MA, Allahresania A, Esmaeilpour M. Green Chem. 2019; 21: 1718
For recent reviews containing Ni-catalyzed cross-couplings involving C–O bond, see: