Categories: C-H Bond Formation >
Reduction of acid chlorides
The use of hydrosilanes as reducing agents in the presence of a palladium catalyst enables an efficient synthesis of aldehydes from acid chlorides. A simple mixture of commercially available Pd(dba)2 and Mes3P catalyzed the reduction of various acid chlorides including aliphatic acid chlorides and α,β-unsaturated acid chlorides to the corresponding aldehydes in good to high yields under mild reaction conditions.
T. Fujihara, C. Cong, T. Iwai, J. Terao, Y. Tshuji, Synlett, 2012, 23, 2389-2392.
Polymethylhydrosiloxane (PMHS) under Pd(0) catalysis can efficiently reduce aryl acid chlorides to their corresponding aldehydes in the presence of fluoride without requiring an additional reductant.
K. Lee, R. E. Maleczka, Jr., Org. Lett., 2006, 8, 1887-1888.