DMSO-catalyzed chlorination of alcohols using N-phenylbenzimidoyl chloride |
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Authors: | Qiang Wang Jian Xu Zhou-Qing Xu Ji-Dan Yan |
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Institution: | 1. Department of Chemistry, School of Physics-Chemistry, Henan Polytechnic University, Jiao Zuo, 454003, People’s Republic of China 2. Pharmaron Beijing Limited Co., 6 Taihe Road, BDA, Beijing, 100176, People’s Republic of China 3. Junior Section of Tianjin Nankai Xiangyu School, Tianjin, 300100, People’s Republic of China
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Abstract: | N-phenylbenzimidoyl chloride has been demonstrated as an efficient chlorination reagent catalyzed by dimethyl sulfoxide (DMSO) in conversion of alcohols to corresponding chlorides. The reaction conditions were mild, and most of the substrates gave satisfactory yields. The configuration inversion of the chlorination was proved using optically active phenyl alcohols. The amount of DMSO can be as low as 0.001 eq without reducing the efficiency of the chlorination. A plausible mechanism for the reaction was proposed and proved by experiments. The reaction is stereoselective and potentially chemoselective among primary benzyl alcohols, secondary benzyl alcohols, and unactivated aliphatic alcohols. |
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