Journal of the American Chemical Society · 2017 · 158 citations · 70 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisOrganic SynthesisReaction MechanismsRedox CatalysisRedox ChemistryRedox ReactionsC - H Bond FunctionalizationC-h Bond ActivationCarbon-carbon Bond FormationHeterocycle FunctionalizationMild Reaction ConditionsSelective Bond CleavageTransition-metal-catalyzed Functionalization
Using α,α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.
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