Photoinduced Copper-Catalyzed Site-Selective C(sp2)–C(sp) Cross-Coupling via Aryl Sulfonium Salts

The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C­(sp2)–C­(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approa...

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Veröffentlicht in:Organic letters 2020-09, Vol.22 (17), p.6842-6846
Hauptverfasser: Liang, Lei, Niu, Hong-Ying, Li, Ren-Long, Wang, Yao-Fei, Yan, Jin-Kai, Li, Chang-Gong, Guo, Hai-Ming
Format: Artikel
Sprache:eng
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Zusammenfassung:The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C­(sp2)–C­(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approach for the synthesis of arylalkynes via a Cu-catalyzed Sonogashira-type reaction promoted by visible light is described. This method enables site-selective alkynylation from aryl sulfonium salts derived from diverse arenes to a set of arylalkynes with high selectivity and high functional-group compatibility. Moreover, rapid alkynylation of drug molecules is demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02364