Flavin-iodine coupled organocatalysis for the aerobic oxidative direct sulfenylation of indoles with thiols under mild conditions

被引：67

作者：

Ohkado, Ryoma ^{[1
]}

Ishikawa, Tatsuro ^{[1
]}

Iida, Hiroki ^{[1
]}

机构：

[1] Shimane Univ, Interdisciplinary Grad Sch Sci & Engn, Dept Chem, 1060 Nishikawatsu, Matsue, Shimane 6908504, Japan

来源：

GREEN CHEMISTRY | 2018年 / 20卷 / 05期

关键词：

CATALYZED REGIOSELECTIVE SULFENYLATION; METAL-FREE; MOLECULAR-OXYGEN; VISIBLE-LIGHT; ARYLSULFONYL CHLORIDES; CONTROLLABLE SYNTHESIS; HYDROGEN-PEROXIDE; CATIONIC MICELLE; SULFIDES; 3-SULFENYLATION;

D O I：

10.1039/c8gc00117k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unique coupled redox organocatalysis system using flavin and iodine catalysts efficiently promoted the metal-free aerobic oxidative direct sulfenylation of indoles with thiols at ambient temperature without any sacrificial reagents, except environmentally benign molecular oxygen. Biomimetic flavin catalysis plays multiple roles in aerobic oxidative transformations, not only regenerating I-2 from in situ generated I-, but also converting thiols into disulfides.

引用

页码：984 / 988

页数：5

共 72 条

[1]

Backvall J.-E., 2010, MODERN OXIDATION MET

[2] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[3] A new coupled catalytic system for dihydroxylation of olefins by H2O2 [J].

Bergstad, K ;

Jonsson, SY ;

Bäckvall, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10424-10425

[4] MONOOXYGEN DONATION POTENTIAL OF 4A-HYDROPEROXYFLAVINS AS COMPARED WITH THOSE OF A PERCARBOXYLIC ACID AND OTHER HYDROPEROXIDES - MONOOXYGEN DONATION TO OLEFIN, TERTIARY AMINE, ALKYL SULFIDE, AND IODIDE-ION [J].

BRUICE, TC ;

NOAR, JB ;

BALL, SS ;

VENKATARAM, UV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2452-2463

[5] A new synthesis of 3-arylthioindoles as selective COX-2 inhibitors using PIFA [J].

Campbell, JA ;

Broka, CA ;

Gong, L ;

Walker, KAM ;

Wang, JH .

TETRAHEDRON LETTERS, 2004, 45 (21) :4073-4075

[6] Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides [J].

Chen, Min ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu .

CHEMICAL COMMUNICATIONS, 2012, 48 (95) :11686-11688

[7] Bioinspired Oxidative Aromatizations: One-Pot Syntheses of 2-Substituted Benzothiazoles and Pyridines by Aerobic Organocatalysis [J].

Chen, Shuai ;

Hossain, Mohammad S. ;

Foss, Frank W., Jr. .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08) :1045-1051

[8] Aerobic Organocatalytic Oxidation of Aryl Aldehydes: Flavin Catalyst Turnover by Hantzsch's Ester [J].

Chen, Shuai ;

Foss, Frank W., Jr. .

ORGANIC LETTERS, 2012, 14 (19) :5150-5153

[9] Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts [J].

Chen, Shuai ;

Hossein, Mohammad S. ;

Foss, Frank W., Jr. .

ORGANIC LETTERS, 2012, 14 (11) :2806-2809

[10] Recent Developments in Flavin-based Catalysis [J].

de Gonzalo, Gonzalo ;

Fraaije, Marco W. .

CHEMCATCHEM, 2013, 5 (02) :403-415

← 1 2 3 4 5 6 7 8 →