Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 951-959Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.106
Keywords
azepine; cyclization; gold catalyst; hydroamination; triethynylphosphine
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Funding
- MEXT
- JSPS
- Grants-in-Aid for Scientific Research [09J01922, 23655025] Funding Source: KAKEN
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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.
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