Iodine-Catalyzed Regioselective Sulfenylation of Indoles with Thiols in Water

被引：16

作者：

He, Yongqin ^{[1
]}

Liu, Shengkang ^{[1
]}

Wen, Ping ^{[2
]}

Tian, Wanfa ^{[1
]}

Ren, Xiaoyu ^{[1
]}

Zhou, Qiangxiao ^{[1
]}

Ma, Haojie ^{[1
]}

Huang, Guosheng ^{[1
]}

机构：

[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou, Peoples R China

[2] Baoji Univ Arts & Sci, Dept Chem Engn, Baoji 721016, Peoples R China

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 08期

关键词：

EFFICIENT SULFENYLATION; ARYLTHIOINDOLES; SYSTEM; OXONE; MONO;

D O I：

10.1002/slct.201600257

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel protocol of Iodine catalyzed oxidative 3-sulfenylation of indoles with thiols has been developed using cheap and environment friendly Hydrogen peroxide (30% H2O2) as oxidant. In addition, H2O was firstly used as solvent in this type of reaction, in this method, indoles react with multiple thiols smoothly and various 3-sulfanylindoles were obtained in good to excellent yields.. The extensive scope of substrates, the mild reaction conditions, and the high selection of reaction site delivery promising applications in drug discovery and functional materials. Especially, Indole-1-carboxamides were also compatible with this transformation, and the predictable products were obtained in good yields.

引用

页码：1567 / 1570

页数：4

共 50 条

[41] Iodine-Catalyzed Regioselective Sulfonylation of Quinoline N-Oxides with Sulfonyl Hydrazides
Yu, Haiyang
Pi, Chao
Wang, Yong
Cui, Xiuling
Wu, Yangjie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 124 - 130
[42] Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates
Pathare, Ramdas S.
Patil, Vikas
Kaur, Harpreet
Maurya, Antim K.
Agnihotri, Vijai K.
Khan, Shahnawaz
Devunuri, Nagaraju
Sharon, Ashoke
Sawant, Devesh M.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (37) : 8263 - 8266
[43] Flavin-iodine coupled organocatalysis for the aerobic oxidative direct sulfenylation of indoles with thiols under mild conditions
Ohkado, Ryoma
Ishikawa, Tatsuro
Iida, Hiroki
GREEN CHEMISTRY, 2018, 20 (05) : 984 - 988
[44] Combined experimental/theoretical study on D-glucosamine promoted regioselective sulfenylation of indoles catalyzed by copper
Ge, Xin
Sun, Fengli
Liu, Xuemin
Chen, Xinzhi
Qian, Chao
Zhou, Shaodong
NEW JOURNAL OF CHEMISTRY, 2017, 41 (21) : 13175 - 13180
[45] Iodine-catalyzed esterification of polysaccharides
Biswas, Atanu
Selling, G. S.
Shogren, R. L.
Willett, J. L.
Buchanan, C. M.
Cheng, H. N.
CHIMICA OGGI-CHEMISTRY TODAY, 2009, 27 (04): : 33 - 35
[46] Iodine-catalyzed disulfidation of alkenes
Wang, Xiu-Ren
Chen, Fan
TETRAHEDRON, 2011, 67 (25) : 4547 - 4551
[47] Iodine-Catalyzed Nazarov Cyclizations
Koenig, Jonas J.
Arndt, Thiemo
Gildemeister, Nora
Neudoerfl, Joerg-M.
Breugst, Martin
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 7587 - 7605
[48] Iodine-Catalyzed Etherification of Morroniside
Sunghwa, Fortunatus
Sakurai, Hiroaki
Saiki, Ikuo
Koketsu, Mamoru
CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (01) : 112 - 115
[49] IODINE-CATALYZED AROMATIZATION OF MENTHANES
HO, TL
CHEMISTRY & INDUSTRY, 1987, (08) : 295 - 296
[50] Copper-catalysed regioselective sulfenylation of indoles with sodium sulfinates
Luo, Xiaojun
Liu, Qiang
Zhu, Hongxia
Chen, Huoji
ROYAL SOCIETY OPEN SCIENCE, 2018, 5 (05):

← 1 2 3 4 5 →