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Azolium/Hydroquinone Organo‐Radical Co‐Catalysis: Aerobic C−C‐Bond Cleavage in Ketones
Author(s) -
Nakatsuji Yuya,
Kobayashi Yusuke,
Masuda Sakyo,
Takemoto Yoshiji
Publication year - 2021
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.202004943
Subject(s) - hydroquinone , chemistry , catalysis , bond cleavage , cyclic voltammetry , cleavage (geology) , photochemistry , radical ion , organocatalysis , polymer chemistry , organic chemistry , electrochemistry , materials science , enantioselective synthesis , ion , electrode , composite material , fracture (geology)
Organo‐radical catalysts have recently attracted great interest, and the development of this field can be expected to broaden the applications of organocatalysis. Herein, the first example of a radical‐generating system is reported that does not require any photoirradiation, radical initiators, or preactivated substrates. The oxidative C−C‐bond cleavage of 2‐substituted cyclohexanones was achieved using an azolium salt and a hydroquinone as co‐catalysts. A catalytic mechanism was proposed based on the results of diffusion‐ordered spectroscopy and cyclic voltammetry measurements, as well as computational studies.