Palladium-Catalyzed α-Arylation of Ketones on Solid Support

Significance

The authors have reported the palladium-catalyzed α-arylation of ketones on solid phase using modified Buchwald-Hartwig reaction conditions. Immobilized 4-bromobenzamide 1, which was prepared from polystyrene Rink amide resin, reacted with various aromatic, heteroaromatic, and aliphatic ketones in the presence of 20 mol% Pd₂(dba)₃ and 80 mol% BINAP as catalyst and an excess of NaOt-Bu as base to form the corresponding coupling compounds 2. Subsequent cleavage from the Rink amide resin was carried out with trifluoroacetic acid in dichloro­methane to give the desired α-aryl ketones 3 in moderate to high yield and good to excellent purity.