Rhenium catalyzed sulfoxide reduction

被引：48

作者：

Arterburn, JB

Perry, MC

机构：

[1] Dept. of Chem. and Biochemistry, New Mexico State University, Box 30001 / 3C, Las Cruces

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 44期

关键词：

D O I：

10.1016/0040-4039(96)01836-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient method for the catalytic reduction of sulfoxides to sulfides with triphenylphosphine and the catalyst ReOCl3(PPh(3))(2) (I) is reported. Aryl sulfoxides are reduced faster than alkyl, and the reaction is successful for sterically hindered sulfoxides and those with common organic functional groups. Copyright (C) 1996 Elsevier Science Ltd

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页码：7941 / 7944

页数：4

相关论文

共 26 条

[1] OXIDATIONS OF ER(3) (E=P, AS, OR SB) BY HYDROGEN-PEROXIDE - METHYLRHENIUM TRIOXIDE AS CATALYST [J].

ABUOMAR, MM ;

ESPENSON, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :272-280

[2] SULPHOXIDES .I. OXIDATION OF TERVALENT PHOSPHORUS COMPOUNDS BY DIMETHYL SULPHOXIDE [J].

AMONOONEIZER, EH ;

RAY, SK ;

SHAW, RA ;

SMITH, BC .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (AUG) :4296-+

[3] POLYSTYRYLDIPHENYLPHOSPHINE AS A DEOXYGENATION REAGENT FOR SULFOXIDES [J].

AMOS, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1311-1313

[4] Rhenium-catalyzed oxidation of sulfides with phenyl sulfoxide [J].

Arterburn, JB ;

Nelson, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2260-2261

[5] OXYGEN-EXCHANGE BETWEEN SULFOXIDES AND SULFIDES - HYDROGEN-CHLORIDE CATALYZED REACTION BETWEEN PARA-CHLOROPHENYL METHYL SULFOXIDE AND DIBUTYL SULFIDE [J].

BOVIO, A ;

MIOTTI, U .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (02) :172-177

[6] OXYGEN ATOM TRANSFER BETWEEN RHENIUM, SULFUR, AND PHOSPHORUS - CHARACTERIZATION AND REACTIVITY OF RE(O)CL3(ME2S)(OPPH3) AND RE(O)CL3(CNCME3)2 [J].

BRYAN, JC ;

STENKAMP, RE ;

TULIP, TH ;

MAYER, JM .

INORGANIC CHEMISTRY, 1987, 26 (14) :2283-2288

[7] DEOXYGENATION OF SULFOXIDES - REVIEW [J].

DRABOWICZ, J ;

NUMATA, T ;

OAE, S .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1977, 9 (02) :63-83

[8] METAL-CENTERED OXYGEN ATOM TRANSFER-REACTIONS [J].

HOLM, RH .

CHEMICAL REVIEWS, 1987, 87 (06) :1401-1449

[9] A THERMODYNAMIC SCALE FOR OXYGEN ATOM TRANSFER-REACTIONS [J].

HOLM, RH ;

DONAHUE, JP .

POLYHEDRON, 1993, 12 (06) :571-589

[10] Effects of conjugation and aromaticity on the sulfoxide bond [J].

Jenks, WS ;

Matsunaga, N ;

Gordon, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1275-1283