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

J Am Chem Soc

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.

Published: June 2017

We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5531279PMC
http://dx.doi.org/10.1021/jacs.7b04364DOI Listing

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We report the first example of a silyl-Negishi reaction between secondary zinc organometallics and silicon electrophiles. This palladium-catalyzed process provides direct access to alkyl silanes. The delicate balance of steric and electronic parameters of the employed DrewPhos ligand is paramount to suppressing isomerization and promoting efficient and selective cross-coupling.

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