Tandem Double-Cross-Coupling/Hydrothiolation Reaction
of 2‑Sulfenyl Benzimidazoles with Boronic Acids
Posted on 2019-07-11 - 20:03
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.
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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. https://doi.org/10.1021/acs.orglett.9b02067
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AUTHORS (4)
AL
Alexandra
Basilio Lopes
MC
Mickael Choury
PW
Patrick Wagner
MG
Mihaela Gulea
KEYWORDS
bromobenzylsulfenylproduct structureboronic acidstereoselectivetandem palladium-catalyzed reactionSuzukihydrothiolationregioselectiveassistancebenzimidazolereincorporationtransformationsulfenyl moietySulfenylincorporationDouble-Cross-CouplingBoronic Acidsprocess resultsdesulfenylativestereodefined alkenyl sulfideBenzimidazolebond