Lopes, Alexandra Basilio Choury, Mickael Wagner, Patrick Gulea, Mihaela Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2‑Sulfenyl Benzimidazoles with Boronic Acids A new tandem palladium-catalyzed reaction involving a Suzuki–Miyaura coupling, a desulfenylative coupling, and a hydrothiolation of a triple bond is reported. Notably, the desulfenylative coupling occurs without copper­(I) assistance and the hydrothiolation is totally regioselective and stereoselective. The overall process results in the double incorporation of the boronic acid and the reincorporation of the sulfenyl moiety into the product structure. Starting from 2-(bromobenzylsulfenyl)-1-propargyl benzimidazoles, the transformation led to variously substituted benzimidazoles bearing a stereodefined alkenyl sulfide. bromobenzylsulfenyl;product structure;boronic acid;stereoselective;tandem palladium-catalyzed reaction;Suzuki;hydrothiolation;regioselective;assistance;benzimidazole;reincorporation;transformation;sulfenyl moiety;Sulfenyl;incorporation;Double-Cross-Coupling;Boronic Acids;process results;desulfenylative;stereodefined alkenyl sulfide;Benzimidazole;bond 2019-07-11
    https://acs.figshare.com/articles/journal_contribution/Tandem_Double-Cross-Coupling_Hydrothiolation_Reaction_of_2_Sulfenyl_Benzimidazoles_with_Boronic_Acids/8862260
10.1021/acs.orglett.9b02067.s001