Difluorocarbene-Enabled Synthesis of 3-Alkenyl-2-oxindoles from <i>ortho</i>-Aminophenylacetylenes
Shanglin Chen, Hua Huang, Xin Li, Xingxing Ma, Jianke Su, Qiuling Song
Abstract
Herein, we report a transition-metal-free [4 + 1] cyclization pathway from difluorocarbene and ortho -amino aryl alkynone, rendering an effective and universal strategy for the construction of 3-alkenyl-2-oxindoles. Our strategy starts from cheap and accessible ortho -amino aryl alkynone instead of the direct indole skeleton; moreover, in situ generated difluorocarbene from commercially available halogenated difluoroalkylative reagents enables the cleavage of a C–N bond and formation of new C–N bonds and C–C bonds.
Topics & Concepts
DifluorocarbeneReagentChemistryIndole testArylCycloadditionStereochemistryBond cleavageCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisAlkylFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods