Journal
ORGANIC LETTERS
Volume 11, Issue 14, Pages 3064-3067Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol9010882
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- MEXT
- JSPS
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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.
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