(α-Ethoxyvinyl)tributyltin acts as a masked acetylating agent in the palladium catalyzed reaction with various organic halides, such as aryl bromides, vinyl bromides, benzyl chloride, and allyl chloride, giving, after hydrolysis of the resulting reaction mixture, good yields of the corresponding ketone product.

Direct transformation of aryl bromides to benzylic alcohols by means of hydroxymethyltributyltin in the presence of palladium complex was attained in moderate yields, although the catalytic efficiencies were rather low, and the reaction could not be applied to aryl bromides having strong electron-withdrawing group. These problems were solved by using the trimethylsilyl-protected tin compound.

The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with bromobenzene in the presence of a catalytic amount of PdCl,(o-tolyl,P), was found to give a-phenyl ketones in good yields with essentially complete retention of the acetate regiochemistry.

Die Arylbromide (I) reagieren mit dem Enolacetat (H) in Gegenwart von TributyIzinn‐methylat (Reaktionsmechunismus) zu den α‐substituienen Ketonen (III).

The reaction of aryl bromides with methoxymethyltributyltin in the presence of a catalytic amount of dichlorobis(triphenylphosphine)palladium was found to give arylmethyl methyl ether. The reaction is a novel aromatic methoxymethylation.