Palladium-Catalyzed Reaction of Tributyltin Hydride with Acyl Chlorides. A Mild, Selective, and General Route to Aldehydes

Article abstract of DOI:10.1021/jo00335a023

Tetrakis(triphenylphosphine)palladium(0), various palladium(II) complexes, and even PdCl2 in the presence of triphenylphosphine catalyze the reaction of acyl chlorides with tri-n-butyltin hydride to specifically give aldehydes under very mild conditions and in very good yields.The reaction is quite general and tolerates the presence of many other reducible groups on the acyl chloride.Tetrakis(triphenylphosphine)palladium(0) also catalyzes the tributyltin hydride reduction of α,β-unsaturated carbonyl compounds to saturated carbonyl compounds; however, α,β-unsaturated acyl chlorides may be reduced to α,β-unsaturated aldehydes with a very good selectivity.The mechanism of the catalytic reductions is discussed.