Regioselective Chlorolactonization of Styrene-Type Carboxylic Esters and Amides via PhICl2-Mediated Oxidative C-O/C-Cl Bond Formations

被引：11
|
作者：
Xing, Linlin [1 ]
Zhang, Yong [1 ]
Zhang, Yilin [2 ]
Ai, Zhenkang [1 ]
Li, Xuemin [1 ]
Du, Yunfei [1 ]
Deng, Jun [3 ]
Zhao, Kang [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China
[2] West Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
[3] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
基金：
中国国家自然科学基金;
关键词：
POLYVALENT IODINE; TRANS-STILBENE-2-CARBOXYLIC ACIDS; HYPERVALENT IODINE(III); ALKENES; HALOFUNCTIONALIZATION; DIFUNCTIONALIZATION; HALOLACTONISATION; BROMOCYCLIZATION; DICHLORINATION; HALOGENATION;
D O I：
10.1021/acs.joc.9b02022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile method employing styrene-type carboxylic esters or amides in the presence of PhICl2 in CH3CN was developed to achieve the synthesis of 6-endo products 3,4-dihydroisocoumarins or 3,4-dihydroisocoumarin-l-imines in good to high yields. This metal-free regioselective intramolecular chlorolactonization process was proposed to involve a PhICl2-mediated oxidative C-O bond formation followed by C-Cl bond formation.
引用
收藏
页码：13832 / 13840
页数：9
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