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Synthesis
DOI: 10.1055/a-2626-7083
DOI: 10.1055/a-2626-7083
Review
Published as part of the Special Topic Dedicated to Prof. Paul Knochel
Cross-Coupling Reactions Between Alkynyl Metals and (Pseudo)Halides Induced by Earth-Abundant Transition Metals (Mn, Fe, Co, Ni, Cu)
Dedication
Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.
Abstract
In this review, we describe the synthesis of substituted alkynes by C–C bond formation, using cross-coupling reactions between alkynyl metals (alkynyl Grignard reagents and alkynyl zinc derivatives) with (pseudo)halides, catalyzed by abundant and inexpensive transition metals such as manganese, iron, cobalt, nickel, and copper. These cross-coupling reactions are chemo- and stereoselective.
Keywords
Alkynyl Grignard reagents - Alkynylzinc derivatives - (Pseudo)halides - Cross-couplings - Transition metalsPublication History
Received: 02 May 2025
Accepted after revision: 03 June 2025
Article published online:
07 August 2025
© 2025. Thieme. All rights reserved.
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References
- 1a Chinchilha R, Najera C. Chem Rev 2007; 107: 874-922
- 1b Liu J, Lam WY, Tang BZ. Chem Rev 2009; 109: 5799-5867
- 2a For ex, see. Cossy J, Pete J-P. Tetrahedron Lett 1986; 26: 573-574
- 2b Cossy J, Pete J-P. Tetrahedron Lett 1986; 26: 2369-2370
- 3a See for ex. Eckhard M, Fu GC. J Am Chem Soc 2003; 125: 13642-13643
- 3b Altenhoff G, Wurtz S, Glorius F. Tetrahedron Lett 2006; 47: 2925-2928
- 3c Vechorkin O, Barmaz D, Proust V, Hu XL. J Am Chem Soc 2009; 131: 12078-12079
- 4a See for ex. Zhao YS, Wang HB, Hou XH. et al. J Am Chem Soc 2006; 128: 15048-15049
- 4b Chen M, Zheng XL, Li WQ, He J, Lei AW. J Am Chem Soc 2010; 132: 4101-4103
- 4c Shi W, Liu C, Lei AW. Chem Soc Rev 2011; 40: 2761-2776
- 4d Liu C, Zhang H, Shi W, Lei AW. Chem Rev 2011; 111: 1780-1824
- 5a See for ex. Smith SW, Fu GC. J Am Chem Soc 2008; 130: 12645-12647
- 5b Smith SW, Fu GC. Angew Chem Int Ed 2008; 47: 9334-9336
- 5c Cahiez G, Gager O, Buendia J. Angew Chem Int Ed 2010; 49: 1278-1281
- 5d Thaler T, Guo LN, Mayer P, Knochel P. Angew Chem Int Ed 2011; 50: 2174-2177
- 6 Cahiez G, Moyeux A, Buendia J, Duplais C. J Am Chem Soc 2007; 129: 13788-13789
- 7 Zhou Z, Xue W. J Organomet Chem 2009; 694: 599-603
- 8 Mastropierro P, Platten AWJ, Kennedy AR, Hevia E, Uzelac M. Chem – Eur J 2023; 29: e202300593
- 9 Cahiez G, Duplais C, Buendia J. Angew Chem Int Ed 2009; 48: 6731-6734
- 10a Kude J, Hayase S, Kawatsura M, Itoh T. Heteroat Chem 2011; 22: 397-404
- 10b Itoh T. Heterocycles 2016; 92: 1373-1395
- 11 Hatajuyama T, Yoshimoto Y, Gabriel T, Nakamura M. Org Lett 2008; 10: 5341-5344
- 12 Berben LA, Long JR. Inorg Chem 2005; 44: 8459-8468
- 13a Kochi JK. Acc Chem Res 1974; 7: 351-360
- 13b Kauffmann T. Angew Chem Int Ed 1996; 35: 386-403
- 13c Bogdanovic B, Schwichardi M. Angew Chem Int Ed 2000; 39: 4610-4612
- 13d Uchiyazma M, Matsumoto Y, Nakamura S. et al. J Am Chem Soc 2004; 126: 8755-8759
- 13e Furstner A, Martin R, Krause H, Siedel G, Goddard R, Lehmann C. J Am Chem Soc 2008; 130: 8773-8787
- 14 Hatakeyama T, Okada Y, Yoshimoto Y, Nakamura M. Angew Chem Int Ed 2011; 50: 10973-10976
- 15 Nast R, Urban FZ. Z Anorg Allg Chem 2005; 44: 8459-8468
- 16a For review see. Sawamoto M, Ando I, Sawamoto M. Chem Rev 2001; 101: 3689-3746
- 16b Uchiike C, Terashima T, Ouchi M, Ando T, Kamigaito M, Sawamoto M. Macromolecules 2007; 40: 8658-8662
- 16c Kawamura M, Sunada Y, Kai H. et al. Adv Synth Catal 2009; 351: 2086-2090
- 17a Formation of radicals by cleavage of C-halide bonds in iron-catalyzed reactions, see. Asahara T, Seno M, Ohtani N. Bull Chem Soc Jpn 1973; 46: 3193-3197
- 17b Davis R, Durrant JLA, Khazai NMS. J Organomet Chem 1990; 386: 229-239
- 17c Forti L, Ghelti F, Pagnoni UM. Tetrahedron 1997; 53: 4419-4426
- 17d Vallée F, Mousseau JJ, Charrette AB. J Am Chem Soc 2010; 132: 1514-1516
- 17e Liu W, Cao H, Lei A. Angew Chem Int Ed 2010; 49: 2004-2008
- 18 Kneebone JL, Brennessel WW, Neidig ML. J Am Chem Soc 2017; 139: 6988-7003
- 19 Cheung CW, Pen P, Hu X. Org Lett 2014; 16: 2566-2569
- 20 Smith JM, Qin T, Merchant RR. et al. Angew Chem Int Ed 2017; 56: 11906-11910
- 21 Schlubach HH, Franzen V. Justus Liebigs Ann Chem 1951; 572: 115-121
- 22 Black HK, Horn DHS, Weedon BCL. J Chem Soc 1954; 1704-1709
- 23 Shirakawa E, Sato T, Imazaki Y, Kimura T, Hayashi T. Chem Commun 2007; 4513-4515
- 24a Wakabayashi K, Yorimitsu H, Oshima K. J Am Chem Soc 2001; 123: 5374-5375
- 24b Ohmiya H, Wakabazyashi K, Yorimitsu H, Oshima K. Tetrahedron 2006; 62: 2207-2213
- 25 Kuno A, Saino N, Kamachi T, Okamoto S. Tetrahedron Lett 2006; 47: 2591-2594
- 26 Ohmiya H, Yorimitsu H, Oshima K. Org Lett 2006; 8: 3093-3096
- 27 Hsu SF, Ko C-W, Wu Y-T. Adv Synth Catal 2011; 353: 1756-1762
- 28 Hamman JM, Haas D, Tüllmann C-P, Karaghiosoff K, Knochel P. Org Lett 2016; 18: 4778-4781
- 29a Someya H, Ohmiyaz H, Oshima K. Org Lett 2007; 9: 1565-1567
- 29b Someya H, Ohmiyaz H, Oshima K. Tetrahedron 2007; 63: 8609-8618
- 30 Fang K, Xie M, Zhang Z, Ning P, Shu G. Tetrahedron Lett 2013; 54: 3819-3821
- 31 Clayden J, Cooney JJA, Julia M. J Chem Soc Perkin Trans 1995; 7-14
- 32 Tobisu M, Takahira T, Ohtsuki A, Chatani N. Org Lett 2015; 17: 680-683
- 33 Madec M, Pujol S, Henryon V, Férézou J-P. Synlett 1995; 435-438
- 34 Vechorkin O, Godinat A, Scopelliti R, Hu X. Angew Chem Int Ed 2011; 50: 11777-11781
- 35 Hua S-K, Hu Q-P, Ren J, Zeng B-B. Synthesis 2013; 45: 518-526
- 36 Zhu Y, Xiong T, Han W, Shi Y. Org Lett 2014; 16: 6144-6147
- 37a Chen Y-H, Ellwart M, Malakhov V, Knochel P. Synthesis 2017; 49: 3215-3223
- 37b Liu X, Wang J, Li J. Synlett 2022; 33: 1688-1694
- 37c Stathakis CI, Monolikakes SM, Knochel P. Org Lett 2013; 15: 1302-1305
- 37d For ex. Chen Y-H, Tüllmann CP, Ellwart M, Knochel P. Angew Chem Int Ed 2017; 56: 9236-9239
- 37e Osano M, Kida T, Yonekura K, Tsuchimoto T. Adv Synth Catal 2019; 361: 2825-2831
- 38 Hung TT, Huang CM, Tsai FY. ChemCatChem 2012; 4: 540-545
- 39 Hammann JM, Thomas L, Chen Y-H, Haas D, Knochel P. Org Lett 2017; 19: 3847-3850
- 40 Thomas L, Lutter FH, Hofmayer MS, Karaghiosoff K, Knochel P. Org Lett 2018; 20: 2441-2444
- 41 Liu X-G, Zhou C-J, Lin E. et al. Angew Chem Int Ed 2018; 57: 13096-13100
- 42 Zhu D-L, Xu P, Wu Q, Li H-Y, Lang J-P, Li H-X. J Org Chem 2020; 85: 9201-9212
- 43 Penney JM, Miller JA. Tetrahedron Lett 2004; 45: 4989-4992
- 44 Hofmayer MS, Lutter FH, Grokenberger L, Hammann JM, Knochel P. Org Lett 2019; 21: 36-39
- 45 Aukland MH, Talbot FJT, Fernadez-Sams JA, Ball M, Puliis AP, Procter DJ. Angew Chem Int Ed 2018; 57: 9785-9789
- 46 He X-Y, Wang ZX. Chem Commun 2021; 11988-11991
- 47a Yang B, Wang Z-X. J Org Chem 2017; 82: 4542-4549
- 47b Yang B, Wang Z-X. Org Lett 2020; 22: 1599-1604
- 48 Thapa S, Kafle A, Gurung SK, Montoya A, Riedel P, Giri R. Angew Chem Int Ed 2015; 54: 8236-8240