Organic Letters · 2022 · 47 citations · 42 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCatalytic MechanismsOrganic SynthesisArylation ReactionsEnantioselective SynthesisFunctional Group ToleranceIndole ChemistryIndole DerivativesIndole SynthesisMild Reaction ConditionsSubstrate Scope
The Rh(III)-catalyzed highly enantioselective C2-arylation of indole derivatives with 1-diazonaphthoquinones is reported. In the presence of 2.5 mol % SCpRh complex and 20 mol % AgNO3, the C2-arylation reactions of indoles proceeded smoothly, affording a wide range of C2-arylated indole atropisomers in good yields and enantioselectivity (≤96% yield, ≤97% ee) under mild conditions. The method displays a broad substrate scope and good functional group tolerance.
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Biotinylated Rh(III) Complexes in Engineered Streptavidin for Accelerated Asymmetric C–H Activation
Todd K. Hyster, Livia Knörr, Thomas R. Ward et al. · Science · 2012 · 806 citations · Full text