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

共 72 条

[41] Copper-Catalyzed Three-Component Reaction for Regioselective Aryl- and Heteroarylselenation of Indoles using Selenium Powder [J].

Luo, Dongping ;

Wu, Ge ;

Yang, Hang ;

Liu, Miaochang ;

Gao, Wenxia ;

Huang, Xiaobo ;

Chen, Jiuxi ;

Wu, Huayue .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) :4485-4493

[42] Vanadium-catalyzed sulfenylation of indoles and 2-naphthols with thiols under molecular oxygen [J].

Maeda, Y ;

Koyabu, M ;

Nishimura, T ;

Uemura, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) :7688-7693

[43] Gold Catalysis in Micellar Systems [J].

Minkler, Stefan R. K. ;

Lipshutz, Bruce H. ;

Krause, Norbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (34) :7820-7823

[44] Synthesis and odour evaluation of novel sulfur-containing cyclic acetals [J].

Miyazawa, Yamato ;

Masuda, Yui ;

Ohmori, Yuichiro ;

Katsuta, Ryo ;

Nukada, Tomoo ;

Ishigami, Ken .

FLAVOUR AND FRAGRANCE JOURNAL, 2019, 34 (01) :43-51

[45] Efficient hydroxyl radical production with Sodium salts of surfactants ozonation for treatment of organic acid pollutants in wastewater [J].

Nawaz, Faheem ;

Khan, Barkat Ullah ;

Ullah, Hamid ;

Islam, Zia Ul ;

Khan, Ghulam Ullah ;

Khayam, Muhammad ;

Waseem, Muhammad ;

Khan, Gohram ;

Khan, Muhammad Amjad .

ENVIRONMENTAL TECHNOLOGY & INNOVATION, 2021, 22

[46] Ternary copper(II)-polypyridyl enantiomers: aldol-type condensation, characterization, DNA-binding recognition, BSA-binding and anticancer property [J].

Ng, Chew-Hee ;

Wang, Wai-San ;

Chong, Kok-Vei ;

Win, Yip-Foo ;

Neo, Kian-Eang ;

Lee, Hong-Boon ;

San, Swee-Lan ;

Abd Rahmand, Raja Noor Zaliha Raja ;

Leonge, Weng Kee .

DALTON TRANSACTIONS, 2013, 42 (28) :10233-10243

[47] Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals [J].

Oderinde, Martins S. ;

Frenette, Mathieu ;

Robbins, Daniel W. ;

Aquila, Brian ;

Johannes, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) :1760-1763

[48] Flavin-iodine coupled organocatalysis for the aerobic oxidative direct sulfenylation of indoles with thiols under mild conditions [J].

Ohkado, Ryoma ;

Ishikawa, Tatsuro ;

Iida, Hiroki .

GREEN CHEMISTRY, 2018, 20 (05) :984-988

[49] Iodine-Catalyzed Synthesis of 3-Arylthioindoles Employing a 1-Aryltriazene/CS2 Combination as a New Sulfenylation Source [J].

Pandey, Anand Kumar ;

Chand, Shiv ;

Singh, Rahul ;

Kumar, Saurabh ;

Singh, Krishna Nand .

ACS OMEGA, 2020, 5 (13) :7627-7635

[50] Using the Thiyl Radical for Aliphatic Hydrogen-Atom Transfer: Thiolation of Unactivated C-H Bonds [J].

Panferova, Liubov, I ;

Zubkov, Mikhail O. ;

Kokorekin, Vladimir A. ;

Levin, Vitalij V. ;

Dilman, Alexander .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) :2849-2854

← 1 2 3 4 5 6 7 8 →