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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
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)
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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
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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: