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  • Title: New Radical Borylation Pathways for Organoboron Synthesis Enabled by Photoredox Catalysis.
    Author: Qi J, Zhang FL, Jin JK, Zhao Q, Li B, Liu LX, Wang YF.
    Journal: Angew Chem Int Ed Engl; 2020 Jul 27; 59(31):12876-12884. PubMed ID: 32232933.
    Abstract:
    Radical borylation using N-heterocyclic carbene (NHC)-BH3 complexes as boryl radical precursors has emerged as an important synthetic tool for organoboron assembly. However, the majority of reported methods are limited to reaction modes involving carbo- and/or hydroboration of specific alkenes and alkynes. Moreover, the generation of NHC-boryl radicals relies principally on hydrogen atom abstraction with the aid of radical initiators. A distinct radical generation method is reported, as well as the reaction pathways of NHC-boryl radicals enabled by photoredox catalysis. NHC-boryl radicals are generated via a single-electron oxidation and subsequently undergo cross-coupling with the in-situ-generated radical anions to yield gem-difluoroallylboronates. A photoredox-catalyzed radical arylboration reaction of alkenes was achieved using cyanoarenes as arylating components from which elaborated organoborons were accessed. Mechanistic studies verified the oxidative formation of NHC-boryl radicals through a single-electron-transfer pathway.
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