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Issue 8, 2017
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Pincer cobalt complex-catalyzed Z-selective hydrosilylation of terminal alkynes

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Abstract

A phosphine-iminopyridine (PCNN) cobalt-catalyzed Z-selective hydrosilylation of terminal alkynes with Ph2SiH2 has been developed for the synthesis of (Z)-β-vinylsilanes with high regio- and stereoselectivity and wide functional group tolerance. Furthermore, the Co-catalyzed hydrosilylations of unsymmetrical arylalkyl disubstituted internal alkynes afford syn-addition products with unique regioselectivity: the silyl group is added to the alkyl-substituted carbon, instead of the aryl-substituted carbon. The (Z)-β-vinylsilane products are further applied to Pd-catalyzed Hiyama–Denmark cross-couplings for stereoselective synthesis of (Z)-disubstituted alkenes.

Graphical abstract: Pincer cobalt complex-catalyzed Z-selective hydrosilylation of terminal alkynes

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Supplementary files

Article information


Submitted
30 Mar 2017
Accepted
23 Apr 2017
First published
28 Apr 2017

This article is Open Access

Org. Chem. Front., 2017,4, 1517-1521
Article type
Research Article

Pincer cobalt complex-catalyzed Z-selective hydrosilylation of terminal alkynes

X. Du, W. Hou, Y. Zhang and Z. Huang, Org. Chem. Front., 2017, 4, 1517
DOI: 10.1039/C7QO00250E

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