title: Palladium-catalyzed reactions of arylindium reagents prepared directly from aryl iodides and indium metal.
abstract: 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 approximately 85% of the indium metal employed can be recovered by reduction of the residual indium salts with zinc(0).
authors: Department of Chemistry and Biochemistry, California State University-Northridge, Northridge, California 91330, USA.
authors: Vardan
authors: V
authors: Papoian
authors: Thomas
authors: T
authors: Minehan
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D018021:Lithium Chloride / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001713:Biphenyl Compounds; D006847:Hydrocarbons, Iodinated; D007659:Ketones; D009942:Organometallic Compounds; D007204:Indium; D010165:Palladium; D018021:Lithium Chloride