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Metal-Free Difunctionalization of Alkynes with 2-Chlorodithiane for Synthesis of β-Ketodithianes

Junshan Lai, Lixia Tian, Xing Huo, Yuan Zhang, Xingang Xie and Shouchu Tang*

*School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China, Email:

J. Lai, L. Tian, X. Huo, Y. Zhang, X. Xie, S. Tang, J. Org. Chem., 2015, 80, 5894-5899.

DOI: 10.1021/acs.joc.5b00187

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An oxidative coupling method for alkyne difunctionalization under metal-catalyst-free conditions affords various β-ketodithianes in very good yields with high regioselectivities. The reaction provides valuable dithianes with controlled formation of a new C-C bond and a C-O bond via a radical coupling pathway.

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Key Words

oxidation, C-C coupling, 1,3-dithianes, oxygen

ID: J42-Y2015