Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions

被引：422
|
作者：
Sato, K
Hyodo, M
Aoki, M
Zheng, XQ
Noyori, R [1 ]
机构：
[1] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan
来源：
TETRAHEDRON | 2001年 / 57卷 / 13期
关键词：
green chemistry; hydrogen peroxide; oxidation; phase-transfer catalyst; quaternary ammonium salts; sulfides; sulfones; sulfoxides;
D O I：
10.1016/S0040-4020(01)00068-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aromatic and aliphatic sulfides are oxidized to sulfoxides or sulfones in high yield with 30% hydrogen peroxide under organic solvent- and halogen-free conditions. Dialkyl and alkyl aryl sulfides are cleanly oxidized to sulfoxides using aqueous hydrogen peroxide without catalysts. The best catalyst for the sulfone synthesis consists of sodium tungstate, phenylphosphonic acid, and methyltrioctyl-ammonium hydrogensulfate. Go-existing primary or secondary alcohol or olefinic moieties are unaffected under such conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2469 / 2476
页数：8
相关论文
共 50 条
  • [1] SELECTIVE OXIDATION OF SULFIDES TO SULFOXIDES/SULFONES BY 30% HYDROGEN PEROXIDE
    He, Ying
    Ma, Xiaoyun
    Ji, Hai Feng
    Zha, Xin Bing
    Jiang, Hongliang
    Lu, Ming
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2012, 187 (07) : 822 - 830
  • [2] Oxidation of Sulfides with Hydrogen Peroxide to Sulfoxides and Sulfones
    Sharipov, A.Kh., 1600, Maik Nauka-Interperiodica Publishing (76):
  • [3] Oxidation of Sulfides with Hydrogen Peroxide to Sulfoxides and Sulfones
    A. Kh. Sharipov
    Russian Journal of Applied Chemistry, 2003, 76 : 108 - 113
  • [4] Oxidation of sulfides with hydrogen peroxide to sulfoxides and sulfones
    Sharipov, AK
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2003, 76 (01) : 108 - 113
  • [5] Selective hydrogen peroxide oxidation of sulfides to sulfoxides or sulfones with MWW-type titanosilicate zeolite catalyst under organic solvent-free conditions
    Kon, Yoshihiro
    Yokoi, Toshiyuki
    Yoshioka, Masato
    Tanaka, Shinji
    Uesaka, Yumiko
    Mochizuki, Takehisa
    Sato, Kazuhiko
    Tatsumi, Takashi
    TETRAHEDRON, 2014, 70 (41) : 7584 - 7592
  • [6] Organic Solvent- and Halide-Free Oxidation with Hydrogen Peroxide
    Chishiro, Takefumi
    Kon, Yoshihiro
    Sato, Kazuhiko
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (11) : 1085 - 1092
  • [7] CaF2 Catalyzed Chemoselective Oxidation of Sulfides to Sulfoxides with Hydrogen Peroxide Under Solvent-Free Conditions
    Rostami, Amin
    Pourshiani, Omid
    Gheisarzade, Sajede
    LETTERS IN ORGANIC CHEMISTRY, 2016, 13 (03) : 201 - 205
  • [8] Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide
    Kirihara, Masayuki
    Yamamoto, Junya
    Noguchi, Takuya
    Hirai, Yoshiro
    TETRAHEDRON LETTERS, 2009, 50 (11) : 1180 - 1183
  • [9] Effective oxidation of sulfides to sulfoxides with hydrogen peroxide under transition-metal-free conditions
    Golchoubian, Hamid
    Hosseinpoor, Farideh
    MOLECULES, 2007, 12 (03): : 304 - 311
  • [10] A practical method for alcohol oxidation with aqueous hydrogen peroxide under organic solvent- and halide-free conditions
    Sato, K
    Aoki, M
    Takagi, J
    Zimmermann, K
    Noyori, R
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (10) : 2287 - 2306
12345