Electrochemical borylation of carboxylic acids
Lisa M. Barton, Longrui Chen, Donna G. Blackmond, Phil S. Baran
Abstract
Significance Boronic acids are one of the most useful functional groups in organic chemistry and can be used as intermediates in synthesis or as key motifs in medicines. This work describes an extremely simple and economical way to use electrochemistry to convert carboxylic acids, through the intermediacy of redox-active esters, to boronic acids. The scope of this reaction is broad, the mechanism has been thoroughly studied, and it can be easily scaled up. Finally, application to the synthesis of a complex polycyclopropane natural product is demonstrated.
Topics & Concepts
BorylationNatural productModular designElectrochemistrySubstrate (aquarium)ScalabilityCombinatorial chemistryCyclopropaneScope (computer science)Carboxylic acidChemistryReagentAlkylOrganic chemistryComputer scienceNanotechnologyMaterials scienceElectrodeEcologyBiologyProgramming languageDatabaseArylPhysical chemistryRing (chemistry)Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques