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Nucleophilic Addition of Sulfonamides to Bromoacetylenes: Facile Preparation of Pyrroles

Masahito Yamagishi, Ken Nishigai, Takeshi Hata and Hirokazu Urabe*

*Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501 Japan, Email: hurabebio.titech.ac.jp

M. Yamagishi, K. Nishigai, T. Hata, H. Urabe, Org. Lett., 2011, 13, 4873-4875.

DOI: 10.1021/ol201952b (free Supporting Information)


Abstract

Nucleophilic addition of sulfonamides to 1-bromo-1-alkynes provided (Z)-N-(1-bromo-1-alken-2-yl)-p-toluenesulfonamides in good yield and in a highly regio- and stereoselective manner. A subsequent reaction in the presence of a palladium catalyst under Heck conditions afforded substituted pyrroles in good yield.

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Key Words

Enamines, Sulfonamides, Pyrroles


ID: J54-Y2011-2680