Facile S-alkyl thiocarbamate synthesis by a novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur

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• 作者：Mizuno ; Takumi ; Takahashi ; Junko ; Ogawa ; Akiya
• 关键词：S-alkyl thiocarbamates ; DBU ; carbon monoxide ; sulfur ; carbonylation
• 刊名：Tetrahedron
• 出版年：2003
• 出版时间：February 17, 2003
• 年：2003
• 卷：59
• 期：8
• 页码：1327-1331
• 全文大小：143 K

文摘

A novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamates. In the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), S-alkyl thiocarbamates are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C). In the absence of DBU, however, no formation of S-alkyl thiocarbamate is observed. The present DBU-assisted carbonylation can also be applied to new synthetic methods for benthiocarb and orthobencarb (herbicides) and carbamoyl chlorides.