Premium
Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides
Author(s) -
Park Gyurim,
Yi Seung Yeon,
Jung Jaehun,
Cho Eun Jin,
You Youngmin
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603517
Subject(s) - bibenzyl , catalysis , chemistry , photoredox catalysis , photochemistry , quantum yield , combinatorial chemistry , photocatalysis , organic chemistry , fluorescence , physics , quantum mechanics
The photoredox catalytic coupling of halomethyl arenes to bibenzyl derivatives has been demonstrated. The catalytic protocol employed the Hantzsch ester, potassium phosphate, and a photoactive cyclometalated Ir III complex catalyst. A photochemical quantum yield as high as 20 % was obtained. The catalytic mechanism was investigated in detail by performing photophysical and electrochemical measurements, as well as by quantum chemical calculations. The results suggest that two‐electron mediation might be responsible for the improved photon economy. The reaction protocol was compatible with halomethyl arenes that contain a variety of functional groups. Finally, the synthetic utility of our protocol was demonstrated by the preparation of a natural dihydrostilbenoid, brittonin A.