ArticleJournal of the American Chemical Society2017
Mechanistic Studies on Rhodium-Catalyzed Enantioselective Silylation of Aryl C-H Bonds.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds.Angewandte Chemie (International ed. in English) · 2022Review
- Catalytic Net Oxidative C-C Activation and Silylation of Cyclopropanols with a Traceless Acetal Directing Group.ACS catalysis · 2022Article
- HCoordination chemistry reviews · 2021Article
- Site-selective functionalization of remote aliphatic C-H bondsChemical science · 2020Review
- Comparative DFT study of metal-free Lewis acid-catalyzed C-H and N-H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope.RSC advances · 2019Article
- Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes.Chemical science · 2019Article
- A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.Chemical Society reviews · 2018Review
- Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.Journal of the American Chemical Society · 2018Article
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2 authors.
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Abstract
Several classes of enantioselective silylations of C-H bonds have been reported recently, but little mechanistic data on these processes are available. We report mechanistic studies on the rhodium-catalyzed, enantioselective silylation of aryl C-H bonds. A rhodium silyl dihydride and a rhodium norbornyl complex were prepared and determined to be interconverting catalyst resting states. Kinetic isotope effects indicated that the C-H bond cleavage step is not rate-determining, but the C-H bond cleavage and C-Si bond-forming steps together influence the enantioselectivity. DFT calculations indicate that the enantioselectivity originates from unfavorable steric interactions between the substrate and the ligand in the transition state leading to the formation of the minor enantiomer.
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