Synthesis 2020; 52(02): 311-319
DOI: 10.1055/s-0039-1690717
paper
© Georg Thieme Verlag Stuttgart · New York

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C–S Vinylation Using NiX2 Salts and Alkyl Phosphites

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Mark Lautens
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada   Email: mark.lautens@utoronto.ca
› Author Affiliations
We thank the University of Toronto (UofT), the Natural Science and Engineering Research Council (NSERC), Alphora Research Inc. and Kennarshore Inc. for financial support.
Further Information

Publication History

Received: 22 August 2019

Accepted after revision: 28 September 2019

Publication Date:
24 October 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