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Indium-Mediated Synthesis of Benzylic Hydroperoxides

Yuxuan Hou, Jinjin Hu, Ruigang Xu, Shulei Pan, Xiaofei Zeng*, Guofu Zhong*

*College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China, Email: chemzxfhznu.edu.cn, zgfhznu.edu.cn

Y. Hou, J. Hu, R. Xu, S. Pan, X. Zeng, G. Zhong, Org. Lett., 2019, 21, 4428-4432.

DOI: 10.1021/acs.orglett.9b01070 (free Supporting Information)


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Abstract

Indium(0) mediates an efficient synthesis of benzylic hydroperoxides in very good yields from a broad range of benzyl bromides under aerobic conditions at room temperature. In addition, a tandem hydroperoxidation-Michael addition of (E)-1-(bromomethyl)-2-(2-nitrovinyl)benzene was also demonstrated.

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proposed mechanism

synthetic utility of the hydroperoxidation reaction



Key Words

peroxides, indium


ID: J54-Y2019