Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C-H Bonds with NaCl/Oxone at Room Temperature

被引：61
|
作者：
Zhao, Mengdi [1 ]
Lu, Wenjun [1 ]
机构：
[1] Shanghai Jiao Tong Univ, Dept Chem, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 17期
基金：
中国国家自然科学基金;
关键词：
POSITIVE HALOGEN COMPOUNDS; TERT-BUTYL HYPOCHLORITE; RADICAL CHLORINATION; HYDROCARBONS; ALKANES; PEROXYMONOSULFATE; ACTIVATION; CATALYST; OXONE(R); BROMINE;
D O I：
10.1021/acs.orglett.7b02153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible light-induced monochlorination of cyclohexane with sodium chloride (5:1) has been successfully accomplished to afford chlorocyclohexane in excellent yield by using Oxone as the oxidant in H2O/CF3CH2OH at room temperature. Other secondary and primary alkyl sp(3) C-H bonds of cycloalkanes and functional branch/linear alkanes can also be chlorinated, respectively, under similar conditions. The selection of a suitable organic solvent is crucial in these efficient radical chlorinations of alkanes in two-phase solutions. It is studied further by the achievement of high chemoselectivity in the chlorination of the benzyl sp(3) C-H bond or the aryl sp(2) C-H bond of toluene.
引用
收藏
页码：4560 / 4563
页数：4
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