Journal
ORGANIC LETTERS
Volume 21, Issue 1, Pages 180-184Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03651
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Funding
- Board of Research in Nuclear Sciences (BRNS), Mumbai [37(2)/14/12/2015/BRNS/10549]
- Indian Institute of Science Education and Research (IISER), Bhopal
- UGC
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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.
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