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Dirhodium-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines

Michael J. Nutt, Jack W. Annear, Kieran D. Jones, Gavin R. Flematti, Stephen A. Moggach and Scott G. Stewart*

*School of Molecular Sciences, The University of Western Australia (M310), 35 Stirling Highway, Crawley, WA 6009, Australia, Email: scott.stewartuwa.edu.au

M. J. Nutt, J. W. Annear, K. D. Jones, G. R. Flematti, S. A. Moggach, S. G. Stewart, J. Org. Chem., 2023, 88, 11968-11979.

DOI: 10.1021/acs.joc.3c01259


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Abstract

A dirhodium(II) complex catalyzes a reaction of 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates to provide a range of C2-substituted 2,3-dehydropiperazines. The reaction proceeds through an α-imino rhodium carbene 1,3-insertion into N-H followed by a base-mediated cyclization. Terminal alkynes can be used as substrate in a three-step, one-pot operation, forming the triazole in situ.

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Key Words

N-heterocycles


ID: J42-Y2023