Issue 8, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
30 mar 2017
Accepted
23 apr 2017
First published
28 apr 2017
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2017,4, 1517-1521

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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