Iridium-Catalyzed Benzylamine C-H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group.

The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as solvent. A good range of benzylamines could be selectively monoalkenylated without interfering with further aza-Michael addition. The kinetic isotope effect experiments showed that C-H activation is not the rate-limiting step. In addition, a five-membered iridacycle species was isolated and established as the possible key intermediate.