Dimethylaluminum methaneselenolate—a useful reagent for the preparation of selenoesters. A new friedel-crafts acylation procedure promoted by Cu(I)

Abstract

The preparation of a new aluminum reagent, dmiethylaluminum methaneselenolate (Me 2AlSeMe) is described. The reactivity of this aluminum reagent toward a variety of organic substrates has been studied. Me 2AlSeMe will convert O-alkyl esters to selenoesters in high yield. These selenoesters function as extremely reactive acyl transfer agents and are converted to acids, esters, and amides on reaction with water, alcohols or amines in the presence of a selenophilic metal cation. The selenoesters will, moreover, acylate reactive arenes and heterocyclic compounds when cuprous triflate is employed as the selenophilic metal cation. This latter transformation constitutes a new transition metal promoted variant of the Friedel-Crafts acylation reaction.