Micelle-mediated multicomponent cross-coupling in water: general construction of 3-chalcogenylindoles

被引：11

作者：

He, Xi ^{[1
]}

Song, Weili ^{[1
]}

Liu, Xuemin ^{[1
]}

Huang, Jiamin ^{[3
]}

Feng, Ruilong ^{[1
]}

Zhou, Shaodong ^{[2
]}

Hong, Jianquan ^{[1
]}

Ge, Xin ^{[1
]}

机构：

[1] Jiangnan Univ, Sch Chem & Mat Engn, Key Lab Synthet & Biol Colloids, Minist Educ, Wuxi 214122, Peoples R China

[2] Zhejiang Univ, Coll Chem & Biol Engn, Zhejiang Prov Key Lab Adv Chem Engn Manufacture Te, Hangzhou 310007, Peoples R China

[3] Ningbo Zhongtian Engn Co Ltd, Ningbo 315048, Peoples R China

来源：

GREEN CHEMISTRY | 2023年 / 25卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CATALYZED SULFENYLATION; INDOLES; SULFUR; ARYL; THIOLS; FUNCTIONALIZATION; 3-SULFENYLINDOLES; HETEROCYCLES; THIOLATION; IODIDES;

D O I：

10.1039/d2gc03694k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and sustainable multicomponent cross-coupling for the construction of 3-chalcogenylindoles from indoles with aryl iodides and elemental sulfur under the aqueous micellar condition was developed. Elemental sulfur is employed as an eco-friendly and easy-handling sulfur source of thiyl radicals. The synergic effect between Cu catalysts and micelles formed by the sugar-based surfactant GluM can stabilize thiyl radicals, further initiating C-S coupling at the readily available indoles by single-electron transfer. Notably, the aqueous micellar system can not only be recycled and reused with good yields, but can also be extended to the conversion of elemental selenium.

引用

页码：1311 / 1321

页数：12

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