使用原位生成的ICl、IBr、BrCl、I₂和Br₂对1,2-二卤代烯烃进行区域和立体选择性合成。
Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.
作者信息
Zeng Xiaojun, Liu Shiwen, Yang Yuhao, Yang Yi, Hammond Gerald B, Xu Bo
机构信息
Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China.
出版信息
Chem. 2020 Apr 9;6(4):1018-1031. doi: 10.1016/j.chempr.2020.03.011.
Abstract
We describe a catalyst-free 1,2--dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system-a combination of NXS electrophile and alkali metal halide (MX) in acetic acid-is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the generation of XX electrophile, including ICl, IBr, BrCl, I and Br.
摘要
我们描述了一种无催化剂的炔烃1,2-二卤化反应，该反应具有前所未有的底物范围以及独特的区域和立体选择性。这种通用的二卤化体系——NXS亲电试剂与碱金属卤化物（MX）在乙酸中的组合——适用于多种类型的炔烃（富电子或贫电子炔烃、内炔和端炔，或O-、N-、S-取代炔烃等杂原子取代的炔烃）。氢键供体溶剂乙酸对于生成包括ICl、IBr、BrCl、I₂和Br₂在内的XX亲电试剂至关重要。
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