Abstract
Rather surprisingly, C-C bond formation through "intermolecular" radical addition to internal ynamides has never been reported. Actually, ynamides are excellent acceptors for "electrophilic" carbon-centered radicals. These processes enable the introduction of functionalized alkyl chains at Cβ, groups that have not yet been introduced via the addition of organometallics. Radical carboiodination affords persubstituted α-iodo-enamides in moderate to high yield. The addition is totally stereoselective. Theoretical support to the mechanism and the scope and limitation of the reaction are discussed.
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