Cooperative Friedel−Crafts Catalysis in Heterobimetallic Regime: Alkylation of Aromatics by π-Activated Alcohols

Abstract

The highly active Friedel-Crafts alkylation (FCA) catalyst, [Ir(COD)Cl(SnCl3)(SnCl4)(arene)]+Cl- (1-SnCl4), is easily generated in one-pot from [Ir(COD)Cl]2 or [Ir(COD)(mu-Cl)Cl(SnCl3)]2 (1) and SnCl4. The reaction of arenes, heteroarenes with benzyl, and allyl alcohols is promoted by 1-SnCl4 (1 mol %) with high turnover frequency. Kinetic evidence is presented to establish FCA pattern. From dual-catalyst combination studies varying the transition metal and main group metal partner, the efficiency of the present catalysts is attributed to the electrophilic "IrIII-SnIV" core.