Pd-catalyzed access to mono- and di-fluoroallylic amines from primary anilines

The Pd-catalyzed highly selective synthesis of mono- and di-2-fluoroallylic amines from gem-difluorocyclopropanes and ubiquitous unprotected primary anilines is herein described. Initial kinetic investigations suggest a first order in the gem-difluorocyclopropane substrate, as well as a circa zeroth order in the aniline coupling partner. The newly produced fluoroallylic motifs should find important applications in synthetic as well as medicinal chemistry and stimulate the further development of coupling methods based on strained cyclic building blocks.

Automated summary

The highly selective synthesis of mono- and di-2-fluoroallylic amines from gem-difluorocyclopropanes and primary anilines using a Pd catalyst is described. Initial kinetic studies suggest a first order reaction with the gem-difluorocyclopropane substrate and a zeroth order reaction with the aniline coupling partner. The newly synthesized fluoroallylic motifs have important applications in synthetic and medicinal chemistry, and can potentially stimulate the development of coupling methods using strained cyclic building blocks.