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
› Institutsangaben
We thank the University of Toronto (UofT), the Natural Science and Engineering Research Council (NSERC), Alphora Research Inc. and Kennarshore Inc. for financial support.
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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

 
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