Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 8, Pages 1517-1521Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7qo00250e
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Funding
- National Natural Science Foundation of China [21272255, 21121062]
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A phosphine-iminopyridine ((PNN)-N-C) cobalt-catalyzed Z-selective hydrosilylation of terminal alkynes with Ph2SiH2 has been developed for the synthesis of (Z)-beta-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)-beta-vinylsilane products are further applied to Pd-catalyzed Hiyama-Denmark cross-couplings for stereoselective synthesis of (Z)-disubstituted alkenes.
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