Rh(III)-Catalyzed Weakly Coordinating 2‑Pyridone-Directed Oxidative Annulation Using Internal Alkynes: A Reversal in Selectivity

A rhodium­(III)-catalyzed Satoh–Miura type oxidative annulation of N-aryl 2-pyridone derivatives is described using internal alkyne as a coupling partner. A weakly coordinating carbonyl group of the 2-pyridone ring is utilized for this transformation. The reaction proceeds with a broad scope and wid...

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Bibliographic Details
Published in:Organic letters 2022-11, Vol.24 (46), p.8470-8475
Main Authors: Bera, Satabdi, Sarkar, Sanhita, Pal, Juthi, Samanta, Rajarshi
Format: Article
Language:English
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Summary:A rhodium­(III)-catalyzed Satoh–Miura type oxidative annulation of N-aryl 2-pyridone derivatives is described using internal alkyne as a coupling partner. A weakly coordinating carbonyl group of the 2-pyridone ring is utilized for this transformation. The reaction proceeds with a broad scope and wide functional group tolerance. The solvent plays an important role in the developed method to furnish a different class of annulated product. A preliminary investigation was carried out to explore the photophysical properties of the obtained polyarylated N-naphthyl 2-pyridones.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03187