Oxygenation of organic sulfides catalyzed by simple Fe(III) salts

被引:20
作者
Villalobos, Leslie [1 ]
Ren, Tong [1 ]
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
关键词
Catalytic oxygenation; Organic sulfide; Fe(III) halides; Hydrogen peroxide; HYDROGEN-PEROXIDE; OXIDATION; SELECTIVITY; EPOXIDATION; SULFOXIDES; H2O2;
D O I
10.1016/j.inoche.2012.11.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Organic sulfide oxygenation by hydrogen peroxide (H2O2) was effectively accomplished by using iron(III) chloride or iron(III) bromide as the catalyst. The distribution of products between sulfoxide and sulfone is strongly solvent-dependent, and a 100% selectivity for sulfoxide was achieved with FeCl3 in a 1:1 methanol/water mixture. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:52 / 54
页数:3
相关论文
共 25 条
[1]   Facile oxygenation of organic sulfides with H2O2 catalyzed by Mn-Me3TACN compounds [J].
Barker, JE ;
Ren, T .
TETRAHEDRON LETTERS, 2004, 45 (24) :4681-4683
[2]   Diruthenium(II,III) bis(tetramethyl-1,3-benzenedipropionate) as a novel catalyst for tert-butyl hydroperoxide oxygenation [J].
Barker, Julia E. ;
Ren, Tong .
INORGANIC CHEMISTRY, 2008, 47 (07) :2264-2266
[3]   pH-induced mechanistic changeover from hydroxyl radicals to iron(IV) in the Fenton reaction [J].
Bataineh, Hajem ;
Pestovsky, Oleg ;
Bakac, Andreja .
CHEMICAL SCIENCE, 2012, 3 (05) :1594-1599
[4]   Recent developments in the synthesis and utilization of chiral sulfoxides [J].
Fernández, I ;
Khiar, N .
CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705
[5]  
Garcia-Ruano J.L., 2002, ORG LETT, V5, P75
[6]   Iron-catalyzed epoxidation of olefins using hydrogen peroxide [J].
Hasan, Kamrul ;
Brown, Nicole ;
Kozak, Christopher M. .
GREEN CHEMISTRY, 2011, 13 (05) :1230-1237
[7]   Oxygen Atom Transfer Reactions from Isolated (Oxo)manganese(V) Corroles to Sulfides [J].
Kumar, Anil ;
Goldberg, Israel ;
Botoshansky, Mark ;
Buchman, Yekaterina ;
Gross, Zeev .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15233-15245
[8]   Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions [J].
Legros, J ;
Bolm, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (32) :4225-4228
[9]   Catalytic Reactivity of a Meso-N-Substituted Corrole and Evidence for a High-Valent Iron-Oxo Species [J].
McGown, Amanda J. ;
Kerber, William D. ;
Fujii, Hiroshi ;
Goldberg, David P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :8040-8048
[10]   Iron-catalyzed olefin cis-dihydroxylation using a bio-inspired N,N,O-ligand [J].
Oldenburg, PD ;
Shteinman, AA ;
Que, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15672-15673