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Divergent Synthesis of Vinyl‐, Benzyl‐, and Borylsilanes: Aryl to Alkyl 1,5‐Palladium Migration/Coupling Sequences
Author(s) -
Han JieLian,
Qin Ying,
Ju ChengWei,
Zhao Dongbing
Publication year - 2020
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.201914740
Subject(s) - organosilicon , palladium , aryl , alkyl , borylation , chemistry , combinatorial chemistry , surface modification , organic chemistry , catalysis
Abstract Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through‐space metal/hydrogen shifts allow functionalization of C−H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5‐palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl‐, benzyl‐, and borylsilanes, constituting a unique C(sp 3 )−H transformation based on a 1,5‐palladium migration process.