Affordable Access

deepdyve-link deepdyve-link
Publisher Website

Direct thionation and selenation of amides using elemental sulfur and selenium and hydrochlorosilanes in the presence of amines.

Authors
  • Shibahara, Fumitoshi
  • Sugiura, Rie
  • Murai, Toshiaki
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jul 16, 2009
Volume
11
Issue
14
Pages
3064–3067
Identifiers
DOI: 10.1021/ol9010882
PMID: 19534478
Source
Medline
License
Unknown

Abstract

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.

Report this publication

Statistics

Seen <100 times