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P F Misco - One of the best experts on this subject based on the ideXlab platform.

E J Corey - One of the best experts on this subject based on the ideXlab platform.

Noboru Morita - One of the best experts on this subject based on the ideXlab platform.

C U Kim - One of the best experts on this subject based on the ideXlab platform.

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  • carbon carbon bond construction using boronic acids and aryl Methyl Sulfides orthogonal reactivity in suzuki type couplings
    Chemical Science, 2013
    Co-Authors: Joel F Hooper, Andrew S Weller, Rowan D Young, Indrek Pernik, Michael C Willis
    Abstract:

    The Rh(I)-catalysed coupling of aryl and alkenyl boronic acids with simple aryl and alkenyl Methyl Sulfides is reported. The process employs bench-stable Rh(I) precatalysts incorporating small bite-angle chelating phosphine ligands (R2PCH2PR2, R = iPr, Cy), shows good functional group tolerance, and proceeds under mild reaction conditions. Importantly, aryl bromide activating groups are inert to the reaction conditions, allowing selective reaction at either a Methyl Sulfide or bromide activating group, depending on catalyst (metal) choice. The scope of the coupling reactions, their combination with Rh-catalysed hydroacylation reactions in cascade processes, together with preliminary mechanistic studies, are all documented.

  • Carbon–carbon bond construction using boronic acids and aryl Methyl Sulfides: orthogonal reactivity in Suzuki-type couplings
    Chemical Science, 2013
    Co-Authors: Joel F Hooper, Andrew S Weller, Rowan D Young, Indrek Pernik, Michael C Willis
    Abstract:

    The Rh(I)-catalysed coupling of aryl and alkenyl boronic acids with simple aryl and alkenyl Methyl Sulfides is reported. The process employs bench-stable Rh(I) precatalysts incorporating small bite-angle chelating phosphine ligands (R2PCH2PR2, R = iPr, Cy), shows good functional group tolerance, and proceeds under mild reaction conditions. Importantly, aryl bromide activating groups are inert to the reaction conditions, allowing selective reaction at either a Methyl Sulfide or bromide activating group, depending on catalyst (metal) choice. The scope of the coupling reactions, their combination with Rh-catalysed hydroacylation reactions in cascade processes, together with preliminary mechanistic studies, are all documented.

  • aryl Methyl Sulfides as substrates for rhodium catalyzed alkyne carbothiolation arene functionalization with activating group recycling
    Journal of the American Chemical Society, 2012
    Co-Authors: Joel F Hooper, Adrian B Chaplin, Carlos Gonzalezrodriguez, Andrew S Weller, Amber L. Thompson, Michael C Willis
    Abstract:

    A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl Methyl Sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a Methyl Sulfide, into the products as an alkenyl Sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl Sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.