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Birch‐Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
Author(s) -
Chatterjee Anamitra,
König Burkhard
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905485
Subject(s) - photochemistry , protonation , chemistry , electron transfer , hydrogen atom , aromaticity , birch reduction , photon , energy transfer , ion , molecule , organic chemistry , chemical physics , alkyl , physics , quantum mechanics
The direct reduction of arenes and heteroarenes by visible‐light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible‐light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy‐transfer and electron‐transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen‐atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.