Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization

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Abstract

The gold-catalyzed, seven-membered ring forming, intramolecular hydroamination of alkynic sulfonamides has been investigated. The protocol, with a semihollow-shaped triethynylphosphine as a ligand for gold, allowed the synthesis of a variety of azepine derivatives, which are difficult to access by other methods. Both alkynic sulfoamides with a flexible linear chain and the benzene-fused substrates underwent 7-exo-dig cyclization to afford the nitrogen-containing heterocyclic seven-membered rings, such as tetrahydroazepine and dihydrobenzazepine, in good yields. © 2011 Ito et al.

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Ito, H., Harada, T., Ohmiya, H., & Sawamura, M. (2011). Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization. Beilstein Journal of Organic Chemistry, 7, 951–959. https://doi.org/10.3762/bjoc.7.106

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