Gold-catalyzed 1,2-oxyalkynylation of N-Allenamides with ethylnylbenziodoxolones

TitleGold-catalyzed 1,2-oxyalkynylation of N-Allenamides with ethylnylbenziodoxolones
Publication TypeJournal Article
Year of Publication2019
AuthorsBanerjee, S, Senthilkumar, B, Patil, NT
JournalOrganic Letters
Volume21
Issue1
Pagination180-184
Date PublishedJAN
Type of ArticleArticle
ISSN1523-7060
Abstract

A gold-catalyzed 1,2-oxyalkynylation of N-allenamides with ethylnylbenziodoxolones (EBXs) has been achieved for the first time. The reaction, which follows a redox-neutral Au(I)/Au(III) catalytic pathway, was enabled in an attempt to exhaust the EBX reagents atom-economically by putting the nucleophilic carboxylate part of EBXs to appropriate use. This constitutes the first example for gold-catalyzed beta-alkynylation of N-allenamides to construct highly valuable 1,3-enynes. The potential of the sequence is further documented by some follow-up transformations.

DOI10.1021/acs.orglett.8b03651
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)6.492
Divison category: 
Organic Chemistry

Add new comment