Gold-Catalyzed Tandem Oxidative Coupling Reaction between β‑Ketoallenes and Electron-Rich Arenes to 2‑Furylmethylarenes

A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C–H func...

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Bibliographic Details
Published in:Organic letters 2021-08, Vol.23 (15), p.5891-5895
Main Authors: Yasukawa, Naoki, Yamada, Yutaro, Furugen, Chikara, Miki, Yuya, Sajiki, Hironao, Sawama, Yoshinari
Format: Article
Language:English
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Summary:A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C–H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C–O and C–C bonds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02007