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Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives

Hetao Xu, Mingxing Ye, Kai Yang, Qiuling Song

2021Organic Letters24 citationsDOI

Abstract

Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron "ate" complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, which exhibit operational simplicity, good functional group tolerance, and a broad substrate scope.

Topics & Concepts

RegioselectivityChemistryFunctional groupBoronCombinatorial chemistryCoupling reactionReaction conditionsSubstrate (aquarium)Coupling (piping)Computational chemistryOrganic chemistryCatalysisGeologyMechanical engineeringEngineeringPolymerOceanographyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods