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

Organic Chemistry Frontiers Pub Date: 2017-04-28 DOI: 10.1039/C7QO00250E

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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