A new approach for the reduction of aryl ammonium salts to arenes or aryl silanes using nickel catalysis is reported. This method displays excellent ligand-controlled selectivity based on the N-heterocyclic carbene (NHC) ligand employed. Utilizing a large NHC in non-polar solvents generates aryl silanes, while small NHCs in polar solvents promote reduction to arenes. Several classes of aryl silanes can be accessed from simple aniline building blocks, including those useful for cross-couplings, oxidations, and halogenations. The reaction conditions are mild, functional group tolerant, and provide efficient access to a variety of benzene derivatives.
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Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes
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The syntheses of [2-(CH 3 ECH 2 )C 6 H 4 ]PbPh 3− n Cl n , ( n = 0, E = O (4), E = S (5); n = 1, E = O (6), E = S (7); n = 2, E = O (8), are described. NMR and single crystal data illustrate significant Pb⋯E interactions increasing as n progresses from 0 to 2. The Pb⋯E interactions stabilize the Pb–aryl bonding to the extent that the reactions of 4 and 5 with Me 2 SnCl 2 result in interchange of a Ph group and Cl to produce 6 and 7, respectively, together with Me 2 PhSnCl.more » « less