Facile 5-endo amidyl radical cyclization promoted by vinylic iodine substitution

Organic Letters
Yu Tang, Chaozhong Li

Abstract

[reaction: see text] BF(3).OEt(2)-catalyzed atom-transfer radical addition of iodoacetamides to alkynes yielded the corresponding vinyl iodides, which upon treatment with (t)BuOCl and I(2) afforded gamma-lactam derivatives in moderate to good yield. The mechanism was proposed to be 5-endo amidyl radical cyclization, and vinylic iodine substitution provided the driving force for the cyclization.

Citations

Oct 7, 2015·Journal of the American Chemical Society·David C MillerRobert R Knowles
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Dec 4, 2014·Angewandte Chemie·Tao Xu, Xile Hu
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Mar 20, 2013·Journal of the American Chemical Society·Zhaodong LiChaozhong Li
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