A MnCl2 Catalyzed Synthesis of Aldehydes from Organohalides by Using Samarium Metal in DMF

Abstract

Catalyzed by MnCl2, a novel coupling reaction between organohalides and N,N-dimethylformamide (DMF) was investigated in the presence of samarium metal under mild conditions. A variety of aliphatic, aromatic or heterocyclic aldehydes can be produced with good yields in one pot. Bromosubstrates showed the most efficient reactivity among the organohalides used in the experiments, and 10 mol% MnCl2 was sufficient to catalyze the reaction. The reaction can be scaled up to the gram level and proceed smoothly. This is the first combination of samarium and manganese in organic synthesis, unlike cuprous iodide or nitrate, manganese chloride can promote the formation of aliphatic aldehydes, and the reaction mechanism was also discussed.