Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2‑Sulfenyl Benzimidazoles with Boronic Acids

Published on 2019-07-11T20:03:59Z (GMT) by
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.

Cite this collection

Lopes, Alexandra

Basilio; Choury, Mickael; Wagner, Patrick; Gulea, Mihaela (2019): Tandem Double-Cross-Coupling/Hydrothiolation Reaction

of 2‑Sulfenyl Benzimidazoles with Boronic Acids. ACS Publications. Collection.