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A Free‐Radical‐Promoted Stereospecific Decarboxylative Silylation of α,β‐Unsaturated Acids with Silanes
Author(s) -
Zhang Lizhi,
Hang Zhaojia,
Liu ZhongQuan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509537
Subject(s) - silanes , organosilicon , silylation , stereospecificity , chemistry , organic chemistry , electron paramagnetic resonance , catalysis , silane , physics , nuclear magnetic resonance
A stereospecific decarboxylative silylation of acrylic and propiolic acids with silanes was developed. This reaction represents the first example of decarboxylative CSi bond formation and provides an efficient and convenient approach to various synthetically useful alkenyl and alkynyl organosilicon compounds through the reaction of α,β‐unsaturated acids with silanes. Spin‐trapping and EPR experiments support a radical addition/elimination process.