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Heterobimetallic Control of Regioselectivity in Alkyne Hydrostannylation: Divergent Syntheses of α- and (E)-β-Vinylstannanes via Cooperative Sn-H Bond Activation

Li-Jie Cheng, Neal P. Mankad*

*Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, Illinois 60607, United States, Email: npmuic.edu

L.-J. Cheng, N. P. Mankad, J. Am. Chem. Soc., 2019, 141, 3710-3716.

DOI: 10.1021/jacs.9b00068 (free Supporting Information)



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Abstract

Heterobimetallic (NHC)Cu-[MCO] catalysts enable the catalytic hydrostannylation of terminal alkynes with Bu3SnH under mild conditions, with Markovnikov/anti-Markovnikov selectivity controlled by the Cu/M pairing. MeIMesCu-FeCp(CO)2 as catalyst provides challenging α-vinylstannanes, whereas IMesCu-Mn(CO)5 as catalyst provides (E)-β-vinylstannanes.

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Key Words

vinylstannanes


ID: J48-Y2019