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Visible-Light-Promoted Desulfurative Alkylation of Alkyl Thianthrenium Salts with Activated Olefins

Xin Li, Weili Si, Zhanhui Liu, Haitao Qian, Tingxue Wang, Shengnan Leng, Jinwei Sun, Yan Jiao and Xuan Zhang*

*School of Chemistry and Materials Science, Institute of Advanced Materials and Flexible Electronics (IAMFE), Nanjing University of Information Science and Technology, 219 Ningliu Road, Nanjing 210044, China, Email:

X. Li, W. Si. Z. Liu, H. Qian, T. Wang, S. Leng, J. Sun, Y. Jiao, X. Zhang, Org. Lett., 2022, 24, 4070-4074.

DOI: 10.1021/acs.orglett.2c01525


The formation of an alkyl thianthrenium salt/Hantzsch ester electron donor-acceptor complex enables a photocatalyst- and metal-free generation of an alkyl radical and a subsequent C(sp3)-C(sp3) bond formation with activated olefins. This protocol tolerates a broad range of functionality and can successfully be used in late-stage functionalization of pharmaceuticals.

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proposed mechanism

Key Words

alkylation, Hantzsch ester, photochemistry

ID: J54-Y2022