Three-component 1,2-carboamination of vinyl boronic esters<i>via</i>amidyl radical induced 1,2-migration
Cai You, Armido Studer
Abstract
-chloro-carbamates/carboxamides to give valuable 1,2-aminoboronic esters. These cascades proceed in the absence of any catalyst upon simple visible light irradiation. Amidyl radicals add to the vinylboron ate complexes followed by oxidation and 1,2-alkyl/aryl migration from boron to carbon to give the corresponding carboamination products. These practical cascades show high functional group tolerance and accordingly exhibit broad substrate scope. Gram-scale reaction and diverse follow-up transformations convincingly demonstrate the synthetic potential of this method.
Topics & Concepts
ChemistryComponent (thermodynamics)Combinatorial chemistryOrganic chemistryPhysicsThermodynamicsRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods