A gentle and efficient route for the deoxygenation of sulfoxides using catecholborane (HBcat; cat 1,2-O2C6H4)

被引：59

作者：

Harrison, DJ

Tam, NC

Vogels, CM

Langler, RF

Baker, RT ^{[1
]}

Decken, A

Westcott, SA

机构：

[1] Mt Allison Univ, Dept Chem, Sackville, NB E4L 1G8, Canada

[2] Los Alamos Natl Lab, Div Chem, Los Alamos Catalysis Initiat, Los Alamos, NM 87545 USA

[3] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 46期

基金：

加拿大自然科学与工程研究理事会;

关键词：

catalysis; catecholborane; deoxygenation; Lewis acid; sulfoxides;

D O I：

10.1016/j.tetlet.2004.09.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of catecholborane (HBcat; cat = 1,2-O2C6H4) to a wide range of sulfoxides affords the corresponding sulfides, dihydrogen, and catBOBcat. The diboron compound catBOBcat acts like a Lewis acid and will coordinate one molecule of the starting sulfoxide. Although deoxygenations with bulky or electron withdrawing sulfoxides are slow, these reactions can be greatly accelerated with the use of excess HBcat or by employing a rhodium catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8493 / 8496

页数：4

共 31 条

[1] Electrochemical enzymatic deoxygenation of chiral sulfoxides utilizing DMSO reductase [J].