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Regiodivergent and Stereoselective Hydrosilylation of 1,3‐Disubstituted Allenes
Author(s) -
Miller Zachary D.,
Dorel Ruth,
Montgomery John
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503521
Subject(s) - hydrosilylation , stereoselectivity , chemistry , catalysis , palladium , allene , nickel , organic chemistry , stereochemistry , combinatorial chemistry
Methods for the highly stereoselective and regiodivergent hydrosilylation of 1,3‐disubstituted allenes have been developed. The synthesis of E allylsilanes is accomplished with palladium NHC catalysts, and trisubstituted Z alkenylsilanes are accessed with nickel NHC catalysts. Unsymmetrically substituted allenes are well tolerated with nickel catalysis and afford Z alkenylsilanes. Evidence for a plausible mechanism was obtained through an isotopic double‐labeling crossover study.