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A Chiral Nitrogen Ligand for Enantioselective, Iridium‐Catalyzed Silylation of Aromatic C−H Bonds
Author(s) -
Su Bo,
Zhou TaiGang,
Li XianWei,
Shao XiaoRu,
Xu PeiLin,
Wu WenLian,
Hartwig John F.,
Shi ZhangJie
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609939
Subject(s) - enantioselective synthesis , silylation , regioselectivity , chemistry , iridium , intramolecular force , catalysis , ligand (biochemistry) , borylation , chiral ligand , bond cleavage , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , alkyl , receptor , aryl
Iridium catalysts containing dative nitrogen ligands are highly active for the borylation and silylation of C−H bonds, but chiral analogs of these catalysts for enantioselective silylation reactions have not been developed. We report a new chiral pyridinyloxazoline ligand for enantioselective, intramolecular silylation of symmetrical diarylmethoxy diethylsilanes. Regioselective and enantioselective silylation of unsymmetrical substrates was also achieved in the presence of this newly developed system. Preliminary mechanistic studies imply that C−H bond cleavage is irreversible, but not the rate‐determining step.