Selective and efficient oxidation of sulfides to sulfoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water

被引：89

作者：

Surendra, K ^{[1
]}

Krishnaveni, NS ^{[1
]}

Kumar, VP ^{[1
]}

Sridhar, R ^{[1
]}

Rao, KR ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 27期

关键词：

sulfides; sulfoxides; oxidation; N-bromosuccinimide; beta-cyclodextrin; biomimetic; water;

D O I：

10.1016/j.tetlet.2005.05.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and highly selective oxidation of sulfides to sulfoxides with N-bromosuccinimide (NBS) catalyzed by beta-cyclodextrin in water has been developed. A series Of Sulfides were oxidized selectively at room temperature in excellent yields. This reaction proceeds without over-oxidation to sulfones under mild conditions using water as a solvent and has many advantages over the existing methodologies. (c) 2005 Published by Elsevier Ltd.

引用

页码：4581 / 4583

页数：3

共 50 条

[1] A simple and highly selective biomimetic oxidation of alcohols and epoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water
Krishnaveni, NS
Surendra, K
Rao, KR
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) : 346 - 350
[2] N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides
Wang, Jianqiang
Shi, Fangmin
Dai, Dongyan
Xiong, Liping
Yang, Yongpo
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2021, 196 (05) : 439 - 443
[3] Oxidation of sulfides with N-bromosuccinimide in the presence of hydrated silica gel
Ali, Mohammed Hashmat
Hartman, Melanie
Lamp, Kimberly
Schmitz, Chad
Wencewicz, Tim
SYNTHETIC COMMUNICATIONS, 2006, 36 (12) : 1769 - 1777
[4] KINETICS AND MECHANISM OF OXIDATION OF ALKYL ARYL SULFIDES BY N-BROMOSUCCINIMIDE
PERUMAL, S
ABBAS, KS
CHANDRASEKARAN, R
INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1989, 28 (07): : 592 - 594
[5] A mild, efficient and selective oxidation of sulfides to sulfoxides
Fraile, JM
García, JI
Lázaro, B
Mayoral, JA
CHEMICAL COMMUNICATIONS, 1998, (17) : 1807 - 1808
[6] An efficient and selective photocatalytic system for the oxidation of sulfides to sulfoxides
Zen, JM
Liou, SL
Kumar, AS
Hsia, MS
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (05) : 577 - +
[7] OXIDATION OF ACETALS WITH N-BROMOSUCCINIMIDE
PRUGH, JD
MCCARTHY, WC
TETRAHEDRON LETTERS, 1966, (13) : 1351 - &
[8] OXIDATION OF LYSOZYME BY N-BROMOSUCCINIMIDE
SRIVASTAVA, VK
BIGELOW, CC
BIOCHIMICA ET BIOPHYSICA ACTA, 1972, 285 (02) : 373 - 376
[9] Selective, metal-free oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with N-bromosuccinimide (NBS) under neutral buffered reaction conditions
Karimi, B.
Zareyee, D.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2008, 5 (Suppl 1) : S103 - S107
[10] REACTIONS OF BETA-HYDROXY SULFOXIDES WITH N-BROMOSUCCINIMIDE
TAGUCHI, H
YAMAMOTO, H
NOZAKI, H
TETRAHEDRON LETTERS, 1973, (27) : 2463 - 2464

← 1 2 3 4 5 →