Reduction of sulfoxides catalyzed by oxo-complexes

被引：56

作者：

Cabrita, Ivania ^{[1
]}

Sousa, Sara C. A. ^{[1
]}

Fernandes, Ana C. ^{[1
]}

机构：

[1] Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 47期

关键词：

Sulfoxides; Oxo-complexes; Silanes; Boranes; OXYGEN-ATOM TRANSFER; EFFICIENT DEOXYGENATION; SELECTIVE DEOXYGENATION; N-OXIDES; MILD; SULFIDES; SYSTEM; RHENIUM; REAGENT; HYDROSILYLATION;

D O I：

10.1016/j.tetlet.2010.09.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work reports the catalytic activity of the oxo-complexes HReO4, MoO2(acac)(2), WO2Cl2, and VO(acac)(2) in the reduction of sulfoxides with PhSiH3 or HBcat. The results obtained showed that the catalyst systems PhSiH3/HReO4 (5 mol %) and HBcat/HReO4 (5 mol %) are highly efficient for the deoxygenation of sulfoxides. The complex MoO2(acac)(2) was also efficient, but the reactions required more time and heating. Finally, the complexes WO2Cl2 and VO(acac)(2) showed a moderate activity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6132 / 6135

页数：4

共 43 条

[1] Molecular rhenium(V) oxotransferases: Oxidation of thiols to disulfides with sulfoxides. The case of substrate-inhibited catalysis [J].

Abu-Omar, MM ;

Khan, SI .

INORGANIC CHEMISTRY, 1998, 37 (19) :4979-4985

[2] Oxygen-transfer reactions of methylrhenium oxides [J].

AbuOmar, MM ;

Appelman, EH ;

Espenson, JH .

INORGANIC CHEMISTRY, 1996, 35 (26) :7751-7757

[3] Rhenium catalyzed sulfoxide reduction [J].

Arterburn, JB ;

Perry, MC .

TETRAHEDRON LETTERS, 1996, 37 (44) :7941-7944

[4] Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Karimi, Ahmad .

SYNTHESIS-STUTTGART, 2008, (16) :2543-2546

[5] A novel method for the deoxygenation of sulfoxides with the PPh3/Br2/CuBr system [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Khedri, Mohammad .

CHEMISTRY LETTERS, 2007, 36 (11) :1324-1325

[6]

BALICKI R, 1991, SYNTHESIS-STUTTGART, P155

[7]

BROWN HC, 1973, SYNTHESIS-STUTTGART, P42

[8] 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

[9] SELECTIVE DEOXYGENATION OF SULFOXIDES WITH THEXYLCHLOROBORANE-METHYL SULFIDE COMPLEX [J].

CHA, JS ;

KIM, JE ;

KIM, JD .

TETRAHEDRON LETTERS, 1985, 26 (52) :6453-6456

[10] Catalyzing aldehyde hydrosilylation with a molybdenum(VI) complex: A density functional theory study [J].

Costa, Paulo Jorge ;

Romao, Carlos C. ;

Fernandes, Ana C. ;

Royo, Beatriz ;

Reis, Patricia M. ;

Calhorda, Maria Jose .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (14) :3934-3941

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