Journal
ORGANIC LETTERS
Volume 21, Issue 15, Pages 5943-5947Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02067
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- CNRS
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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-(bromoben-zylsulfenyl)-1-propargyl benzimidazoles, the transformation led to variously substituted benzimidazoles bearing a stereodefined alkenyl sulfide.
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