Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal

Article abstract of DOI:10.1021/jo801074g

(Chemical Equation Presented) Treatment of aryl iodides with indium metal in the presence of lithium chloride leads to the formation of an organoindium reagent capable of participating in cross-coupling reactions under transition-metal catalysis. Combination with aryl halides in the presence of 5 mol % Cl₂Pd(dppf) furnishes biaryl compounds in good yields; similarly, reaction with acyl halides or allylic acetates/carbonates in the presence of 5-10 mol % palladium catalyst leads to arylketones and allylic substitution products, respectively, in moderate yields. The reactions are tolerant of the presence of protic solvents, and ～85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).