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Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction

Andrew P. Cinderella, Bojan Vulovic and Donald A. Watson*

*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: dawatsonudel.edu

A. P. Cinderella, B. Vulovic, D. A. Watson, J. Am. Chem. Soc., 2017, 139, 7741-7744.

DOI: 10.1021/jacs.7b04364 (free Supporting Information)


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Abstract

A palladium-catalyzed silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles provides direct access to alkyl silanes. The balance of steric and electronic parameters of the employed DrewPhos ligand suppresses isomerization and promotes efficient and selective cross-coupling.


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proposed mechanism



Key Words

Negishi coupling, alkylsilanes


ID: J48-Y2017