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[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.
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Tang et al. (2004) studied this question.
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