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

Austin D. Marchese, Bijan Mirabi, Egor M. Larin, Mark Lautens*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Email:

A. D. Marchese, B. Mirabi, E. M. Larin, M. Lautens, Synthesis, 2020, 52, 311-319.

DOI: 10.1055/s-0039-1690717

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The use of NiI2 as an air-stable Ni(II) precatalyst, and P(OiPr)3 as a cheap and commercially available ligand enables a scalable and robust cross-coupling of various thiophenols with styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.

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Key Words

nickel, cross-coupling, vinyl sulfides, scalable, heterocycles

ID: J66-Y2020