Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 3, Pages 1006-1008Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja312654q
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Funding
- Ministry of Education, Culture, Sports, and Technology (MEXT), Japan
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [21106003, 23350045] Funding Source: KAKEN
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A free-radical-mediated [2 + 2 + 1] cycloaddition reaction comprising acetylenes, amidines, and CO was achieved by radical chain reaction to give five-membered alpha,beta-unsaturated lactams in good yields. Both acyclic and cyclic amidines reacted with a variety of terminal acetylenes to afford monocyclic, bicyclic, and tricyclic lactams. We propose that vinyl radical carbonylation and nucleophilic addition of the amidine onto the resulting a-ketenyl radical give stable intermediates that are ready to undergo five-membered ring closure with elimination of tin radical.
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