Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00032269.xml
CC BY 4.0 · SynOpen 2025; 09(01): 25-63
DOI: 10.1055/a-2464-7776
DOI: 10.1055/a-2464-7776
graphical review
Neoteric Solvents for Metal-Catalyzed Coupling Reactions
This study was carried out within the Agritech National Research Center and received funding from the European Union NextGenerationEU (PIANO NAZIONALE DI RIPRESA E RESILIENZA (PNRR) MISSIONE 4 COMPONENTE 2, INVESTIMENTO 1.4-D.D. 1032 17/06/2022, CN00000022). The authors acknowledge financial support from the Ministero Italiano dell’Università e della Ricerca provided through the ‘LABSolve’ project (Progetti di Ricerca di Rilevante Interesse Nazionale–Bando 2022 Prot. 20229P7PPM).
Abstract
Catalysis is a green methodology aimed at optimizing synthetic procedures by simplifying the design of target molecules and reducing energy and material consumption. However, catalytic reactions often rely on polar aprotic solvents, such as dimethylformamide (DMF) or acetonitrile, which present environmental and health issues. In response, manufacturers and researchers are exploring greener alternatives derived from residual biomass, which reduce the negative environmental impact of traditional solvents. These new classes of solvents are termed ‘neoteric’ in order to distinguish them from traditional solvents with well-established applications. This graphical review highlights key findings on the use of these new solvents in metal-catalyzed coupling reactions.
Publication History
Received: 11 October 2024
Accepted after revision: 07 November 2024
Accepted Manuscript online:
08 November 2024
Article published online:
20 January 2025
© 2025. 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/)
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Byrne F, Jin S, Sherwood J, Rob McElroy C, Farmer TJ, Clark JH, Hunt AJ. Solvents from Waste . In Bio-Based Solvents . Jérôme F, Luque R. John Wiley & Sons; Hoboken: 2017. 49
- 1b Campos JF, Berteina-Raboin S. Catalysts 2022; 12: 48
- 1c Kong D, Dolzhenko AV. Sustainable Chem. Pharm. 2022; 25: 100591
- 1d Wang Y, Dai M, Luo G, Fan J, Clark JH, Zhang S. Chemistry 2023; 5: 2322
- 1e Ghorai S, Nanda D, Ghosh A, Dash PS. Mol. Catal. 2024; 553: 113720
- 1f Aricò F, Aldoshin AS, Tundo P. ChemSusChem 2017; 10: 53
- 1g Sajid M, Farooq U, Bary G, Azim MM, Zhao X. Green Chem. 2021; 23: 9198
- 1h Leita BA, Warden AC, Burke N, O’Shea MS, Trimm D. Green Chem. 2010; 12: 70
- 1i Zhang J, Zhu A, Xu W, Li D, Zhang Y, Duan Z, Wang Y. Chem. Eng. Res. Des. 2021; 174: 386
- 1j Watanabe K, Yamagiwa N, Torisawa Y. Org. Process Res. Dev. 2007; 11: 251
- 1k Shukla K, Srivastava VC. Catal. Rev. 2017; 59: 1
- 1l Melchiorre M, Esposito R, Di Serio M, Abbate G, Lampasi A, Balducci A, Ruffo F. Energies 2021; 14: 4250
- 1m Voutyritsa E, Triandafillidi I, Kokotos CG. Synthesis 2017; 49: 917
- 1n De Schouwer F, Adriaansen S, Claes L, De Vos DE. Green Chem. 2017; 19: 4919
- 1o Leal-Duaso A, Caballero M, Urriolabeitia A, Mayoral JA, García JI, Pires E. Green Chem. 2017; 19: 4176
- 1p Fache F, Jacquot L, Lemaire M. Tetrahedron Lett. 1994; 35: 3313
- 1q Ramachandran PV, Choudhary S. J. Org. Chem. 2023; 88: 15956
- 1r Haus MO, Winter B, Fleitmann L, Palkovits R, Bardow A. Green Chem. 2022; 24: 6671
- 1s Leiva K, Garcia R, Sepulveda C, Laurenti D, Geantet C, Vrinat M, Garcia-Fierro J, Escalona N. Catal. Today 2017; 296: 228
- 1t Rajabi F. Tetrahedron Lett. 2009; 50: 395
- 1u Hibbard JP, Yam JG, Alsalek EB, Bahamonde A. J. Org. Chem. 2022; 87: 12036
- 2a Wan J.-P, Wang C, Zhou R, Liu Y. RSC Adv. 2012; 2: 8789
- 2b Edwards GA, Trafford MA, Hamilton AE, Buxton AM, Bardeaux MC, Chalker JM. J. Org. Chem. 2014; 79: 2094
- 3 Ramgren SD, Hie L, Ye Y, Garg NK. Org. Lett. 2013; 15: 3950
- 4a Mondal M, Bora U. New J. Chem. 2016; 40: 3119
- 4b Campos JF, Scherrmann M.-C, Berteina-Raboin S. Green Chem. 2019; 21: 1531
- 5 Wilson KL, Murray J, Jamieson CWatson A. J. B. Synlett 2018; 29: 650
- 6a Sullivan C, Zhang Y, Xu G, Christianson L, Luengo F, Halkoski T, Gao P. Green Chem. 2022; 24: 7184
- 6b Gautam P, Gupta R, Bhanage BM. Eur. J. Org. Chem. 2017; 3431
- 7a Wilson KL, Murray J, Sneddon HF, Jamieson C, Watson AJ. B. Synlett 2018; 29: 2293
- 7b Valentini F, Di Erasmo B, Ciani M, Chen S, Gu Y, Vaccaro L. Green Chem. 2024; 26: 4871
- 8a Lei P, Mu Y, Wang Y, Wang Y, Ma Z, Feng J, Liu X, Szostak M. ACS Sustainable Chem. Eng. 2020; 9: 552
- 8b Hooshmand SE, Heidari B, Sedghi R, Varma RS. Green Chem. 2019; 21: 381
- 9a Smoleń M, Kędziorek M, Grela K. Catal. Commun. 2014; 44: 80
- 9b Smoleń M, Marczyk A, Kośnik W, Trzaskowski B, Kajetanowicz A, Grela K. Eur. J. Org. Chem. 2019; 640
- 9c Smoleń M, Kośnik W, Gajda R, Woźniak K, Skoczeń A, Kajetanowicz A, Grela K. Chem. Eur. J. 2018; 24: 15372
- 10a Planer S, Jana A, Grela K. ChemSusChem 2019; 12: 4655
- 10b Nienałtowski T, Krzesinski P, Baumert ME, Skoczen A, Suska-Kauf E, Pawlowska J, Kajetanowicz A, Grela K. ACS Sustainable Chem. Eng. 2020; 8: 18215
- 11 Granato AV, Santos AG, dos Santos EN. ChemSusChem 2017; 10: 1832
- 12a Shin HG, Lee HS, Hong EJ, Kim JG. Bull. Korean Chem. Soc. 2021; 42: 502
- 12b Dolzhenko AV. Sustainable Chem. Pharm. 2020; 18: 100322
- 13a Leitch JA, Wilson PB, McMullin CL, Mahon MF, Bhonoah Y, Williams IH, Frost CG. ACS Catal. 2016; 6: 5520
- 13b Leitch JA, Cook HP, Bhonoah Y, Frost CG. J. Org. Chem. 2016; 81: 10081
- 14a Matsidik R, Luzio A, Hameury S, Komber H, McNeill CR, Caironi M, Sommer M. J. Mater. Chem. C 2016; 4: 10371
- 14b Aldrich TJ, Dudnik AS, Eastham ND, Manley EF, Chen LX, Chang RP. H, Melkonyan FS, Facchetti A, Marks TJ. Macromolecules 2018; 51: 9140
- 14c Monks BM, Fruchey ER, Cook SP. Angew. Chem. Int. Ed. 2014; 53: 11065
- 15a Fruchey ER, Monks BM, Cook SP. J. Am. Chem. Soc. 2014; 136: 13130
- 15b Fumagalli F, Warratz S, Zhang S.-K, Rogge T, Zhu C, Stückl AC, Ackermann L. Chem. Eur. J. 2018; 24: 3984
- 15c Mo J, Messinis AM, Oliveira JC. A, Demeshko S, Meyer F, Ackermann L. ACS Catal. 2021; 11: 1053
- 15d Friis SD, Johansson MJ, Ackermann L. Nat. Chem. 2020; 12: 511
- 16a Messinis AM, Finger LH, Hu L, Ackermann L. J. Am. Chem. Soc. 2020; 142: 13102
- 16b Bu Q, Rogge T, Kotek V, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 765
- 16c Tabasso S, Calcio Gaudino E, Rinaldi L, Ledoux A, Larini P, Cravotto G. New J. Chem. 2017; 41: 9210
- 17a Bechtoldt A, Baumert ME, Vaccaro L, Ackermann L. Green Chem. 2018; 20: 398
- 17b Sauermann N, Mei R, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 5090
- 18a Bu Q, Gońka E, Kuciński K, Ackermann L. Chem. Eur. J. 2019; 25: 2213
- 18b Cabrero-Antonino JR, Adam R, Junge K, Beller M. Chem. Sci. 2017; 8: 6439
- 19a Ye L, Thompson BC. ACS Macro Lett. 2021; 10: 714
- 19b Santoro S, Ferlin F, Luciani L, Ackermann L, Vaccaro L. Green Chem. 2017; 19: 1601
- 19c Gandeepan P, Kaplaneris N, Santoro S, Vaccaro L, Ackermann L. ACS Sustainable Chem. Eng. 2019; 7: 8023
- 19d Dalton T, Faber T, Glorius F. ACS Cent. Sci. 2021; 7: 245
- 19e Bijoy R, Agarwala P, Roy L, Thorat BN. Org. Process Res. Dev. 2021; 26: 480
- 19f Deshmukh D, Vagadiya N, Jagtap S, Malasane P. Synthesis 2024; 56: 2329
- 19g Strappaveccia G, Luciani L, Bartollini E, Marrocchi A, Pizzo F, Vaccaro L. Green Chem. 2015; 17: 1071
- 20a Fodor D, Kégl T, Tukacs JM, Horváth AK, Mika LT. ACS Sustainable Chem. Eng. 2020; 8: 9926
- 20b Mahmoudi H, Valentini F, Ferlin F, Bivona LA, Anastasiou I, Fusaro L, Aprile C, Marrocchi A, Vaccaro L. Green Chem. 2019; 21: 355
- 20c Bagherzadeh M, Mahmoudi H, Ataie S, Bahjati M, Kia R, Raithby PR, Vaccaro L. Mol. Catal. 2019; 474: 110406
- 21 Stini NA, Gkizis PL, Kokotos CG. Org. Biomol. Chem. 2023; 21: 351
- 22a Parker HL, Sherwood J, Hunt AJ, Clark JH. ACS Sustainable Chem. Eng. 2014; 2: 1739
- 22b Melchiorre M, Budzelaar PH. M, Cucciolito ME, Esposito R, Santagata E, Ruffo F. Green Chem. 2023; 25: 2790
- 22c Sangon S, Supanchaiyamat N, Sherwood J, McElroy CR, Hunt AJ. React. Chem. Eng. 2020; 5: 1798
- 23a Leal-Duaso A, Mayoral JA, Pires E. ACS Sustainable Chem. Eng. 2020; 8: 13076
- 23b Ferrazzano L, Martelli G, Fantoni T, Daka A, Corbisiero D, Viola A, Ricci A, Cabri W, Tolomelli A. Org. Lett. 2020; 22: 3969
- 24a Fantoni T, Bernardoni S, Mattellone A, Martelli G, Ferrazzano L, Cantelmi P, Corbisiero D, Tolomelli A, Cabri W, Vacondio F, Ferlenghi F, Mor M, Ricci A. ChemSusChem 2021; 14: 2591
- 24b Ismalaj E, Strappaveccia G, Ballerini E, Elisei F, Piermatti O, Gelman D, Vaccaro L. ACS Sustainable Chem. Eng. 2014; 2: 2461
- 25a Liu Y, Voloshkin VA, Scattolin T, Peng M, Van Hecke K, Nolan SP, Cazin CS. J. Eur. J. Org. Chem. 2022; e202200309
- 25b Clark JS. K, Ferguson MJ, McDonald R, Stradiotto M. Angew. Chem. Int. Ed. 2019; 58: 6391
- 26a Liu Y, Scattolin T, Gobbo A, Beliš M, Van Hecke K, Nolan SP, Cazin CS. J. Eur. J. Inorg. Chem. 2021; e202100840
- 26b Pithani S, Malmgren M, Aurell C.-J, Nikitidis G, Friis SD. Org. Process Res. Dev. 2019; 23: 1752
- 27 Fine Nathel NF, Kim J, Hie L, Jiang X, Garg NK. ACS Catal. 2014; 4: 3289
- 28a Park NH, Teverovskiy G, Buchwald SL. Org. Lett. 2014; 16: 220
- 28b Clark JS. K, Voth CN, Ferguson MJ, Stradiotto M. Organometallics 2017; 36: 679
- 29 Zinser CM, Warren KG, Nahra F, Al-Majid A, Barakat A, Islam MS, Nolan SP, Cazin CS. J. Organometallics 2019; 38: 2812
- 30a Monguchi Y, Kitamoto K, Ikawa T, Maegawa T, Sajiki H. Adv. Synth. Catal. 2008; 350: 2767
- 30b Campos JF, Cailler M, Claudel R, Prot B, Besson T, Berteina-Raboin S. Molecules 2021; 26: 1074
- 31a Ostrowska S, Palio L, Czapik A, Bhandary S, Kwit M, Van Hecke K, Nolan SP. Catalysts 2023; 13: 559
- 31b Campos JF, Berteina-Raboin S. Catalysts 2019; 9: 840
- 32 Campos JF, Pacheco-Benichou A, Fruit C, Besson T, Berteina-Raboin S. Synthesis 2020; 52: 3071