Richard M. Wehmeyer

Synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines

Abstract A number of 2,6-disubstituted and 2,3,6-trisubstituted anilines have been prepared via the selective para dehalogenation of the corresponding anilines. Modification of the substituents on the amino nitrogen demonstrates that the selectivity is derived from steric rather than electronic effects. The effects of the choice of formate hydrogen donor, Pd catalyst, solvent, and temperature upon the efficiency and selectivity of the dehalogenation are discussed.

A novel synthesis of 2,6-disubstituted and 2,3,6-trisubstituted anilines

Abstract 2,6-Disubstituted and 2,3,6-trisubstituted anilines have been synthesized by a four-step approach involving the selective reduction of a para halogen of the diacetanilide derivatives utilizing a palladium-on-carbon catalyst and formic acid salts as the in situ hydrogen donor.