Pd-Catalyzed C4-Dearomative Allylation of Benzyl Ammoniums with Allyltributylstannane
Kayashima, Y.; Komatsuda, M.; K.; Muto, K.; Yamaguchi, J.
Chem. Lett. 2020, Advanced Publication. DOI: 10.1246/cl.200216

A dearomative C4-allylation of benzyl ammoniums with allyltributylstannane by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.