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Switching Over of the Chemoselectivity: I2-DMSO-Enabled α,α-Dichlorination of Functionalized Methyl Ketones

Jia-Chen Xiang, Jia-Wei Wang, Peng Yuan, Jin-Tian Ma, An-Xin Wu* and Zhi-Xin Liao*

*Central China Normal University, Wuhan 430079; Southeast University, Nanjing 211189, China, Email: chwuaxmail.ccnu.edu.cn, zxliaoseu.edu.cn

J.-C. Xiang, J.-W. Wang, P. Yuan, J.-T. Ma, A.-X. Wu, Z.-X. Liao, J. Org. Chem., 2022, 87, 15101-15113.

DOI: 10.1021/acs.joc.2c01591


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Abstract

Methyl ketones can undergo dichlorination to afford α,α-dichloroketones in good yields with precise control of the chemoselectivity. Enabled by the I2-dimethyl sulfoxide catalytic system, in which hydrochloric acid only acts as a nucleophilic Cl- donor, this straightforward dichlorination reaction is safe and operator-friendly and has high atomic economy and good functional-group tolerance.


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proposed mechanism



Key Words

chloroketones, DMSO, iodine


ID: J42-Y2022