DABCO-Catalyzed DMSO-Promoted Sulfurative 1,2-Diamination of Phenylacetylenes with Elemental Sulfur and o‑Phenylenediamines: Access to Quinoxaline-2-thiones

The oxidative amination of alkynes typically requires transition metal catalysts and strong oxidants. Herein, we alternatively utilize DABCO as a sulfur-activating catalyst to achieve the sulfurative 1,2-diamination of phenylacetylenes with elemental sulfur and o-phenylenediamines. DMSO was found to...

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Bibliographic Details
Published in:Organic letters 2023-10, Vol.25 (39), p.7225-7229
Main Authors: Tran, Thi Minh Chau, Lai, Nang Duy, Bui, Thai Thanh Thu, Mac, Dinh Hung, Nguyen, Thi Thu Tram, Retailleau, Pascal, Nguyen, Thanh Binh
Format: Article
Language:English
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Chemical Sciences
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Summary:The oxidative amination of alkynes typically requires transition metal catalysts and strong oxidants. Herein, we alternatively utilize DABCO as a sulfur-activating catalyst to achieve the sulfurative 1,2-diamination of phenylacetylenes with elemental sulfur and o-phenylenediamines. DMSO was found to be particularly suitable for use as a terminal oxidant for this three-component process. A mechanistic study has shown that this cascade reaction is triggered by the addition of active sulfur species to the triple bond of phenylacetylenes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02835