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

Alexandra Basilio Lopes | Zendy; Mickaël Choury | Zendy; Patrick Wagner | Zendy; Mihaela Gulea | Zendy

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

Author(s) -

Alexandra Basilio Lopes,

Mickaël Choury,

Patrick Wagner,

Mihaela Gulea

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b02067

Subject(s) - chemistry , propargyl , regioselectivity , tandem , moiety , combinatorial chemistry , aryl , palladium , boronic acid , catalysis , triple bond , stereoselectivity , medicinal chemistry , stereochemistry , double bond , organic chemistry , materials science , composite material , alkyl

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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