Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2‑Sulfenyl Benzimidazoles with Boronic Acids Alexandra Basilio Lopes Mickael Choury Patrick Wagner Mihaela Gulea 10.1021/acs.orglett.9b02067.s001 https://acs.figshare.com/articles/journal_contribution/Tandem_Double-Cross-Coupling_Hydrothiolation_Reaction_of_2_Sulfenyl_Benzimidazoles_with_Boronic_Acids/8862260 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. 2019-07-11 20:03:59 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