<scp>Iron‐Catalysed</scp> C(sp<sup>2</sup>)‐H Borylation with Expanded Functional Group Tolerance<sup>†</sup>
Luke Britton, Jamie H. Docherty, Gary S. Nichol, Andrew P. Dominey, Stephen P. Thomas
Abstract
Comprehensive Summary Arene C(sp 2 )‐H bond borylation offers direct and efficient access to aryl boronic esters. Using in situ catalyst activation and photoirradiation, the iron‐catalysed C(sp 2 )‐H borylation reaction of carboarenes, pyrroles, and indoles has been developed using only bench‐stable pre‐catalysts and reagents. Good functional group tolerance was observed including those not reported using previous methods (ArNH 2 , ArOH, ArSiR 3 , ArP(O)(OR) 2 , ArC(O)NR 2 ). Mechanistic studies revealed iron‐catalysed reductive deoxygenation, C—F protodefluorination, and a demethylation of aryl methyl ethers by C—O sigma bond hydroboration.
Topics & Concepts
ChemistryBorylationHydroborationDeoxygenationCatalysisFunctional groupArylMedicinal chemistryReagentDemethylationBoraneOrganic chemistryPolymerDNA methylationGene expressionGeneBiochemistryAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions