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Synthesis 2020; 52(02): 311-319
DOI: 10.1055/s-0039-1690717
DOI: 10.1055/s-0039-1690717
paper
A Simplified Protocol for the Stereospecific Nickel-Catalyzed C–S Vinylation Using NiX2 Salts and Alkyl Phosphites
Autor*innen
We thank the University of Toronto (UofT), the Natural Science and Engineering Research Council (NSERC), Alphora Research Inc. and Kennarshore Inc. for financial support.
Weitere Informationen
Publikationsverlauf
Received: 22. August 2019
Accepted after revision: 28. September 2019
Publikationsdatum:
24. Oktober 2019 (online)

Abstract
A Ni-catalyzed C–S cross-coupling using only NiI2 (0.5–2.5 mol%) and P(OiPr)3 (2.0–10.0 mol%) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690717.
- Supporting Information (PDF) (opens in new window)
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References
- 1a Gandeepam P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
- 1b Petrone DA, Ye J, Lautens M. Chem. Rev. 2016; 116: 8003
- 1c Miao J, Ge H. Eur. J. Org. Chem. 2015; 7859
- 1d Jana R, Pathak TP, Sigman MP. Chem. Rev. 2011; 111: 1417
- 2a Jones KD, Power DJ, Bierer D, Gericke KM, Stewart SG. Org. Lett. 2018; 20: 208
- 2b Xu X.-B, Liu J, Zhang J.-J, Wang Y.-W, Peng Y. Org. Lett. 2013; 15: 550
- 2c Jammi S, Barua P, Rout L, Saha P, Punniyamurthy T. Tetrahedron Lett. 2008; 49: 1484
- 2d Yatsumonji Y, Okada O, Tsubouchi A, Takeda T. Tetrahedron 2006; 62: 9981
- 2e Gendre F, Yand M, Diaz P. Org. Lett. 2005; 7: 2719
- 2f Cristau HJ, Chabaud B, Labaudiniere R, Christol H. J. Org. Chem. 1986; 51: 875
- 3a Marchese A, Kersting L, Lautens M. Org. Lett. 2019; 21: 7163
- 3b Marchese AD, Lind F, Mahon Á, Yoon H, Lautens M. Angew. Chem. Int. Ed. 2019; 58: 5095
- 3c Yoon H, Marchese AD, Lautens M. J. Am. Chem. Soc. 2018; 140: 10950
- 4 Yatsumonji Y, Ishida Y, Tsubouchi A, Takeda T. Org. Lett. 2007; 9: 4603
- 5a Mandal B, Basu B. RSC Adv. 2014; 4: 13854
- 5b Saxena A, Kumar A, Mozumdar S. J. Mol. Catal. A: Chem. 2007; 269: 35
- 6a Burns JA, Butler JC, Moran J, Whitesides GM. J. Org. Chem. 1991; 56: 2648
- 6b Schäfer K, Asmus A.-D. J. Phys. Chem. 1980; 84: 2156
- 7a Zhang M, Weng Z. Org. Lett. 2019; 21: 5838
- 7b Bryan CS, Braunger JA, Lautens M. Angew. Chem. Int. Ed. 2009; 48: 7064
- 7c Newman SG, Aureggi V, Bryan CS, Lautens M. Chem. Commun. 2009; 5236
- 7d Fang YQ, Lautens M. Org. Lett. 2005; 7: 3549
- 7e Zeidan N, Bognar S, Lee S, Lautens M. Org. Lett. 2017; 19: 5058
- 7f Newman SG, Lautens M. J. Am. Chem. Soc. 2010; 132: 11416
- 8 You H.-Y, Lee K.-J. Synlett 2001; 105
- 9 Qiu C, Yao K, Zhang X, Gong H. Org. Biomol. Chem. 2016; 14: 11332
- 10 Tu H.-Y, Hu B.-L, Deng C.-L, Zhang X.-G. Chem. Commun. 2015; 51: 15558
- 11 Choudhuri K, Pramanik M, Mandal A, Mal P. Asian J. Org. Chem. 2018; 7: 1849
- 12 Yong Y, Rioux RM. Chem. Commun. 2011; 47: 6557
- 13 Savarin C, Srogl J, Liebeskind LS. Org. Lett. 2002; 4: 4309
- 14 Kabir MS, Lorenz M, Van Linn ML, Namjoshi OA, Ara S, Cook JM. J. Org. Chem. 2010; 75: 3626
- 15 Chu C.-M, Tu Z, Wu P, Wang C.-C, Liu J.-T, Kuo C.-W, Shin Y.-H, Yao C.-F. Tetrahedron 2009; 65: 3978
- 16 He L, Guo H, Li Y.-Z, Du G.-F, Dai B. Chem. Commun. 2014; 50: 3719
- 17 Cristau HJ, Chabaud B, Labaudiniere R, Christol H. J. Org. Chem. 1985; 51: 875
- 18 Sim JU, Son HS, Yong J, Baek YM. (Doosan Corp.) Patent KR20150027443 (A), 2015
- 19 Li X, Xu Y, Wu W, Jiang C, Qi C, Jiang H. Chem. Eur. J. 2014; 20: 7911
For select reviews and references therein, see:
Relevant Ni-catalyzed C–S coupling reactions:
Metal-catalyzed oxidative coupling of thiols to disulfides, thus reducing the metal, may be a potential method. For a review of metal-catalyzed oxidative coupling of thiols using metals, see:
For a specific example pertaining to Ni, see:
For an example of disulfide reduction using phosphines or phosphites, see:
For intra-inter molecular cyclizations with Pd generating benzothiophenes, see:
For recent examples of Pd cyclizations of gem-dibromo olefins generating indoles, see: