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JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds.
Journal of the American Chemical Society 2017 September 7
We report highly enantioselective intramolecular, silylations of unactivated, primary C(sp3 )-H bonds. The reactions form dihydrobenzosiloles in high yields with excellent enantioselectivities by functionalization of enantiotopic methyl groups under mild conditions. The reaction is catalyzed by an iridium complex generated from [Ir(COD)OMe]2 and chiral dinitrogen ligands that we recently disclosed. The C-Si bonds in the enantioenriched dihydrobenzosiloles were further transformed to C-Cl, C-Br, C-I, and C-O bonds in final products. The potential of this reaction was illustrated by sequential C(sp3 )-H and C(sp2 )-H silylations and functionalizations, as well as diastereoselective C-H silylations of a chiral, natural-product derivative containing multiple types of C-H bonds. Preliminary mechanistic studies suggest that C-H cleavage is the rate-determining step.
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