Direct Thionation and Selenation of Amides Using Elemental Sulfur and Selenium and Hydrochlorosilanes in the Presence of Amines

被引：80

作者：

Shibahara, Fumitoshi ^{[1
]}

Sugiura, Rie ^{[1
]}

Murai, Toshiaki ^{[1
]}

机构：

[1] Gifu Univ, Dept Chem, Fac Engn, Gifu 5011193, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 14期

关键词：

LAWESSONS REAGENT; MOLECULAR-OXYGEN; BOND FORMATION; THIOAMIDES; BENZOTHIAZOLES; ORGANOLITHIUM; CYCLIZATION; CONVERSION; SECONDARY;

D O I：

10.1021/ol9010882

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of amides with elemental sulfur in the presence of hydrochlorosilanes and amines give the corresponding thioamides in good to high yields. The process takes place via reduction of elemental sulfur by the hydrochlorosilane in the presence of a suitable amine. The methodology can be applied to the selenation of amides by using elemental selenium. Thionation and selenation of an acetyl-protected sialic acid derivative are found to take place selectively at the amide group.

引用

页码：3064 / 3067

页数：4

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