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Metal‐free Photocatalytic Aerobic Oxidative Cleavage of C−C Bonds in 1,2‐Diols
Author(s) -
Zhu Rui,
Zhou Gongyu,
Teng Jianan,
Li Xinglong,
Fu Yao
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202001466
Subject(s) - photocatalysis , chemistry , catalysis , bond cleavage , oxidative cleavage , stoichiometry , oxidative phosphorylation , reaction mechanism , photochemistry , metal , density functional theory , cleavage (geology) , diol , organic chemistry , combinatorial chemistry , computational chemistry , materials science , biochemistry , fracture (geology) , composite material
The preparation of carbonyl compounds by the aerobic oxidative cleavage of C−C bonds in 1,2‐diols under mild reaction conditions is a very significant reaction and is widely employed in various scenarios. Avoiding the use of harmful stoichiometric oxidants and adopting a greener chemical process remain a challenge for this reaction to date. In this manuscript, a heterogeneous metal‐free photocatalytic strategy without any additive was developed for aerobic oxidative cleavage of C−C bonds in 1,2‐diols at ambient conditions with visible light. The reaction mechanism was further studied through a series of control experiments and density functional theory (DFT) calculations. In addition, the catalytic system showed a broad substrates scope, including aliphatic (linear or cyclic) 1,2‐diols, benzylic, alkenyl 1,2‐diols, and α‐hydroxy acids (such as lactic acid). Thus, this strategy could serve as a method for the transformation of 1,2‐diols to corresponding carbonyl compounds by the aerobic oxidative cleavage of C−C bonds.