Alkylboronic acids as alkylating agents: photoredox-catalyzed alkylation reactions assisted by K3PO4† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc05521j

ABSTRACT: Despite the ubiquity of alkylboronic acids in organic synthesis, their utility as alkyl radical precursors in visible-light-induced photocatalytic reactions is limited by their high oxidation potentials. In this study, we demonstrated that an inorganophosphorus compound can modulate the oxidation potentials of alkylboronic acids so that they can act as alkyl radical precursors. We propose a mechanism based on the results of fluorescence quenching experiments, electrochemical experiments, 11B and 31P NMR spectroscopy, and other techniques. In addition, we describe a simple and reliable alkylation method that has good functional group tolerance and can be used for direct C–B chlorination, cyanation, vinylation, alkynylation, and allylation, as well as late-stage functionalization of derivati

SUBMITTER: Yue F 

PROVIDER: S-EPMC9683010 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature