Me₂Zn-Air-Mediated Radical Addition of Primary Alkyls to Imines

Significance

The authors describe a simple method for the radical addition of an alkyl moiety to N-tosyl imines, using alkyl iodides and dimethylzinc-air as a source of alkyl radicals. Both aryl- and alkyl-substituted imines are suitable substrates. The reaction does not require a preformation of organometallic species from the alkyl moiety. On the other hand, the formed alkyl radicals can be used for further easily predictable transformations like intramolecular cyclization, which may open new approaches for the assembly of complex carbon frameworks. The use of Me₂Zn instead of conventional Et₃B for the generation of radicals allowed using primary iodides as substrates.