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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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Published in: | Organic letters 2021-08, Vol.23 (15), p.5891-5895 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.1c02007 |