Regiocontrolled Synthesis of Polysubstituted Pyrroles Starting from Terminal Alkynes, Sulfonyl Azides, and Allenes

Tomoya Miura*, Kentaro Hiraga, Tsuneaki Biyajima, Takayuki Nakamuro and Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: tmiurasbchem.kyoto-u.ac.jp, murakamisbchem.kyoto-u.ac.jp

T. Miura, K. Hiraga, T. Biyajima, T. Nakamuro, M. Murakami, Org. Lett., 2013, 15, 3298-3301.

DOI: 10.1021/ol401340u

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Abstract

1-Sulfonyl-1,2,3-triazoles, readily prepared by copper-catalyzed azide-alkyne cycloaddition, react with allenes in the presence of a nickel(0) catalyst to produce isopyrroles. These intermediates are further converted to a wide range of polysubstituted pyrroles through double bond transposition and Alder-ene reactions.

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Key Words

Pyrroles

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ID: J54-Y2013