Palladium-Catalyzed Arylation of C(sp2)–H Bonds and C(sp3)–H Bonds with 4‑Amino-benzotriazole as the Bidentate Directing Group

The arylation of C­(sp2)–H and C­(sp3)–H bonds in carboxylic acids catalyzed by Pd­(II) with 4-aminobentriazole as the directing group was investigated. In addition to activation of the C­(sp2)–H bond, selective arylation of alkyl carboxylic acids and amino acids in the β position can also be achiev...

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Veröffentlicht in:Journal of organic chemistry 2024-05, Vol.89 (10), p.6966-6973
Hauptverfasser: Li, Chengqian, Wang, Zhuo, Jin, Meina, Song, Zhiguang
Format: Artikel
Sprache:eng
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Zusammenfassung:The arylation of C­(sp2)–H and C­(sp3)–H bonds in carboxylic acids catalyzed by Pd­(II) with 4-aminobentriazole as the directing group was investigated. In addition to activation of the C­(sp2)–H bond, selective arylation of alkyl carboxylic acids and amino acids in the β position can also be achieved. This strategy involved a 5,5-bicyclic Pd intermediate complex whose structure was determined by X-ray single crystal diffraction analysis. Importantly, the DG (directing group) can be easily removed under mild conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00329