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Issue 21, 2020
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Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts as S-arylation sources

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Abstract

A novel and efficient palladium-catalyzed three-component cascade cyclization/arylthiolation has been developed for the assembly of diverse 3-sulfenylindole and 3-sulfenylbenzofuran derivatives from 2-alkynylamines and 2-alkynylphenols, aryldiazonium salts, and Na2S2O3 under aerobic conditions with PEG-200 as an environmentally benign medium. The current study features exceptional functional group tolerance without additional ligands, oxidants or silver salts, and eco-friendly mild reaction conditions. The ionic liquid [C2OHmim]Cl plays a crucial role in this protocol as an environmentally friendly additive. Notably, this procedure represents the first example of the use of aryldiazonium salts as direct S-arylation sources in this type of chemical transformation.

Graphical abstract: Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts as S-arylation sources

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Supplementary files

Article information


Submitted
21 Apr 2020
Accepted
11 May 2020
First published
11 May 2020

Org. Biomol. Chem., 2020,18, 4071-4078
Article type
Paper

Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts as S-arylation sources

J. Li, H. Tang, Z. Lin, S. Yang, W. Wu and H. Jiang, Org. Biomol. Chem., 2020, 18, 4071
DOI: 10.1039/D0OB00828A

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