Diane Dickie - Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations.

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  Thapa, Surendra, Gurung, Santosh K., Dickie, Diane A., Giri,   Ramesh. Angewandte Chemie, International Edition  53 (43) 11620-11624

  Abstract: An efficient copper(I)-catalyzed   coupling of tris(aryl)indium and tris(alkyl)indium reagents with   aryl iodides and aryl bromides is reported. The reaction proceeds   at low catalyst loadings (2 mol%) and generally only requires   0.33 equiv of the triorganoindium reagent with respect to the   aryl halide as all three org. nucleophilic moieties of the   reagent are transferred to the products by a consecutive   transmetalation sequence. The reaction tolerates a variety of   functional groups and sterically hindered substrates.   Furthermore, preliminary mechanistic studies that entailed the   synthesis and characterization of potential reaction   intermediates offered a glimpse of the elementary steps that   constitute the catalytic cycle. Under optimized conditions the   synthesis of the target compds. was achieved by a reaction of   triphenylindium (generated in-situ), tris(2-methylphenyl)indium,   tris(3-methoxyphenyl)indium with aryl iodides, such as   1-iodo-2-methylbenzene, 2-(iodo)pyridine, 2-(iodo)pyrazine,   (iodo)quinoline. A copper catalyst was   bis[2-[bis(1,1-dimethylethyl)phosphino-κP]-N,N-dimethylbenzenamine-κN]di-μ-(met hoxy)dicopper   [i.e., from copper iodide (CuI) and   2-[bis(1,1-dimethylethyl)phosphino]-N,N-dimethylbenzenamine   ligand]. [on SciFinder(R)]

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