A Method for the Synthesis of Thioindoles through Copper-Catalyzed C-S Bond Coupling Reaction

被引：2

作者：

Huang, Jie ^{[1
,2
]}

Li, Jin-Quan ^{[1
]}

Cui, Xin-Yue ^{[1
]}

Qin, Yi-Han ^{[1
]}

Ma, Shi-Jie ^{[1
]}

An, Zi-An ^{[1
]}

Sun, Wen-Wu ^{[1
]}

Wu, Bin ^{[1
,2
,3
]}

机构：

[1] South Cent Minzu Univ, Sch Pharmaceut Sci, Wuhan 430074, Peoples R China

[2] South Cent Minzu Univ, Sch Chem & Mat Sci, Wuhan 430074, Peoples R China

[3] South Cent Minzu Univ, Key Lab Analyt Chem, State Ethn Affairs Commiss, Wuhan 430074, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 01期

基金：

中国国家自然科学基金;

关键词：

REGIOSELECTIVE SULFENYLATION; POTENT INHIBITORS; ISATIS-INDIGOTICA; ACID CATALYST; METAL-FREE; INDOLES; ARYLTHIOINDOLES; DERIVATIVES; IODINE; THIOARYLATION;

D O I：

10.1021/acs.joc.3c02008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein report the copper-catalyzed C-S bond coupling reaction of indoles with N-thiosuccinimides, resulting in moderate to excellent yields of mono- and bis-sulfenylated compounds such as arylthioindoles, alkylthioindoles, selenylated indoles, and cysteine-substituted indoles. Thioarylation and thioglycosylation at the C2 position of indole alkaloids in the Radix Isatidis were achieved via structural modification. The first total syntheses of isatindigotindolosides III and IV have been successfully carried out. The electrophilic sulfenyl bromides generated in situ can play an important role in the catalytic cycle.

引用

页码：245 / 256

页数：12

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