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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Copper-catalyzed monochloromethylazidation to access transformable terminal alkyl chlorides using stoichiometric
Ya-Xuan Zhang1, Kang-Jie Bian1, Ruo-Xing Jin1
1Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China. xswang77@ustc.edu.cn.
Abstract:
Efficient copper-catalyzed 1,2-difunctionalization of alkenes with commercially available BrCH2Cl as a chloromethylating source was carried out, in which mild conditions, high reactivity, excellent functional-group tolerance, and late-stage modification of a bioactive molecule are demonstrated. This strategy offers a solution for the diverse syntheses of nitrogen-containing terminal alkyl chlorides, a common synthetic handle that is promising for multiple derivatizations. Mechanistic studies indicate that a chloromethyl radical is involved in the catalytic cycle.
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