Palladium-Catalyzed 1,2-Alkynylarylation of Vinyl Arenes with Haloalkynes and Arylboronic Acids

We herein disclose a novel palladium-catalyzed 1,2-alkynylarylation of vinyl arenes using haloalkynes and arylboronic acids as coupling partners. This reaction is characterized by broad substrate scope, controllable reaction sequence, and excellent chemo- and regioselectivities. Mechanistic investig...

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Bibliographic Details
Published in:Organic letters 2024-03, Vol.26 (12), p.2354-2358
Main Authors: Ma, Ruize, Fang, Songjia, Jiang, Huanfeng, Wu, Wanqing
Format: Article
Language:English
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Summary:We herein disclose a novel palladium-catalyzed 1,2-alkynylarylation of vinyl arenes using haloalkynes and arylboronic acids as coupling partners. This reaction is characterized by broad substrate scope, controllable reaction sequence, and excellent chemo- and regioselectivities. Mechanistic investigations suggest that the reaction is initiated by regioselective insertion of vinyl arenes into the alkynyl-Pd­(II) species, and the silver salt is crucial for this transformation, serving as both the Lewis acid and halide scavenger. This protocol provides efficient access to new carbon skeletons, which are embedded in the key biologically active motifs.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00051