Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 31, Pages 12876-12884Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915619
Keywords
borylations; N-heterocyclic carbenes; organoborons; photocatalysis; radicals
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Funding
- University of Science and Technology of China
- NSFC [21672195, 21702201, 21971226]
- Fundamental Research Funds for the Central Universities [WK2060190082]
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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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