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