Regiodivergent and Stereoselective Hydrosilylation of 1,3‐Disubstituted Allenes | Zendy

Miller Zachary D. | Zendy; Dorel Ruth | Zendy; Montgomery John | Zendy

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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.

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