Issue 7, 2019

Aerobic conversion of benzylic sp3 C–H in diphenylmethanes and benzyl ethers to C[double bond, length as m-dash]O bonds under catalyst-, additive- and light-free conditions

Abstract

Catalyst-free, additive-free and light-free aerobic conversion of benzylic C–H to C[double bond, length as m-dash]O bonds is reported. A series of C–H bonds in diphenylmethanes and benzyl ethers underwent this transformation to give the targeted products in low to high yields. The reaction mechanism was also investigated using radical trapping, DFT calculations and 18O-labelled experiments, and the results suggested that the present reaction relied on an activation of oxygen by the π bond of the benzene ring.

Graphical abstract: Aerobic conversion of benzylic sp3 C–H in diphenylmethanes and benzyl ethers to C [[double bond, length as m-dash]] O bonds under catalyst-, additive- and light-free conditions

Supplementary files

Article information

Article type
Research Article
Submitted
02 Jan 2019
Accepted
14 Feb 2019
First published
15 Feb 2019

Org. Chem. Front., 2019,6, 952-958

Aerobic conversion of benzylic sp3 C–H in diphenylmethanes and benzyl ethers to C[double bond, length as m-dash]O bonds under catalyst-, additive- and light-free conditions

X. Tian, X. Cheng, X. Yang, Y. Ren, K. Yao, H. Wang and J. Wang, Org. Chem. Front., 2019, 6, 952 DOI: 10.1039/C9QO00004F

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