Photochemical Organocatalytic Aerobic Cleavage of C=C Bonds Enabled by Charge-Transfer Complex Formation

Yi-Xuan Chen, Jun-Tao He, Mei-Chun Wu, Zhi-Lin Liu, Kai Tang, Peng-Ju Xia, Kai Chen, Hao-Yue Xiang*, Xiao-Qing Chen* and Hua Yang*

*College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P.R. China, Email: xianghaoyuecsu.edu.cn, xqchencsu.edu.cn, hyangchemcsu.edu.cn

Y.-X. Chen, J.-T. He, M.-C. Wu, Z.-L. Liu, K. Tang, P.-J. Xia, K. Chen, H.-Y. Xiang, X.-Q. Chen, H. Yang, Org. Lett., 2022, 24, 3920-3925.

DOI: 10.1021/acs.orglett.2c01192

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Abstract

Sodium benzene sulfinate catalyzed a visible-light-driven aerobic oxidative cleavage of olefins to provide the corresponding aldehydes and ketones under transition-metal-free conditions. Notably, α-halo-substituted styrenes proceeded with photoinduced oxidation to finally afford α-halo-acetophenones with halogen migration.

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proposed mechanism

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Key Words

aldehydes, ketones, α-bromoketones, α-iodoketones, organocatalysis, photochemistry, oxygen

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ID: J54-Y2022