Pd-Catalyzed Switchable Access to Imines and Amines from Secondary Alcohols

The use of Pd(OAc)₂ as catalyst for the challenging synthesis of imines through acceptorless alcohol dehydrogenation using secondary alcohols and amines is reported. The reaction requires low catalyst loading, shows high selectivity for the formation of the imine without the need of adding any base or additive, and can be scaled up. Interestingly, when the catalytic reaction is performed in a closed system, in the presence of base, the reaction selectively yields the corresponding amine. To highlight the practical utility of the synthesis of imines, a family of structurally important scaffold, an indole, were synthesized.