Use of 1,3-dipolar reactions for the preparation of SF₅-substituted five-membered ring heterocycles. Pyrroles and thiophenes

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• 作者：William R. Dolbier Jr. ; ^a ; ^{wrd@chem.ufl.edu"" rel=""nofollow} ; Zhaoyun Zheng^a
• 关键词：Pentafluorosulfanyl group ; SF₅ ; Pyrrole synthesis ; Thiophene synthesis ; 1 ; 3-Dipolar cycloadditions
• 刊名：Journal of Fluorine Chemistry
• 出版年：2011
• 出版时间：June 2011
• 年：2011
• 卷：132
• 期：6
• 页码：389-393
• 全文大小：276 K

文摘

In situ-generated unsubstituted, “parent” azomethine and thiocarbonyl ylides are used to prepare a large variety of 3-aryl- and alkyl-substituted, 4-pentafluorosulfanylpyrroles and 3-aryl-substituted, 4-pentafluorosulfanylthiophenes, the latter of which are to our knowledge the first reported SF₅-substituted thiophenes. The 1,3-cycloadditions of these ylides with aryl and alkyl, SF₅-alkynes produce dihydro-pyrroles and thiophenes, which without isolation can then be oxidatively aromatized to the respective pentafluorosulfanylpyrroles and thiophenes in good yield.