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Photoinduced Single‐Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane
Author(s) -
Xia PengJu,
Song Dan,
Ye ZhiPeng,
Hu YuanZhuo,
Xiao JunAn,
Xiang HaoYue,
Chen XiaoQing,
Yang Hua
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913398
Subject(s) - borylation , boranes , photoinduced electron transfer , chemistry , borane , photochemistry , electron transfer , molecule , hydrogen atom , combinatorial chemistry , radical , alkene , organic chemistry , catalysis , boron , alkyl , aryl
A photoinduced SET process enables the direct B−H bond activation of NHC–boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC–boranes, thus obviating the need for extra radical initiators. The resulting NHC–boryl radical was used for the borylation of a wide range of α‐trifluoromethylalkenes and alkenes with diverse electronic and structural features, providing facile access to highly functionalized borylated molecules. Labeling and photoquenching experiments provide insight into the mechanism of this photoinduced SET pathway.