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Synthesis of 3-Methyleneisoindolin-1-ones via Rhodium(III)-Catalyzed C-H/N-H Activation and Annulation of N-Methoxybenzamides with Potassium Vinyltrifluoroborate.
- Source :
-
Chemistry, an Asian journal [Chem Asian J] 2024 Aug 09, pp. e202400718. Date of Electronic Publication: 2024 Aug 09. - Publication Year :
- 2024
- Publisher :
- Ahead of Print
-
Abstract
- Isoindolinones are vital heterocyclic compounds in medicinal chemistry, notable for their diverse bioactivities. Significant attention has been devoted to their preparation; however, existing methods are unsuitable for constructing unsubstituted 3-methyleneisoindolin-1-ones. Herein, we present a rhodium(III)-catalyzed method for synthesizing unsubstituted 3-methyleneisoindolin-1-ones via C-H/N-H activation and annulation of N-methoxybenzamides with potassium (ethenyl)trifluoroborate. This approach offers mild reaction conditions, high regioselectivity, and efficient yields. Interestingly, sterically demanding or heterocyclic N-methoxyaromaticamides resulted in the formation of 2-vinyl(hetero)aromatic amides instead of 3-methyleneisoindolin-1-ones. Mechanistic insights suggest a rhodacycle intermediate pathway, highlighting the method's potential for developing new bioactive isoindolinone derivatives.<br /> (© 2024 Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1861-471X
- Database :
- MEDLINE
- Journal :
- Chemistry, an Asian journal
- Publication Type :
- Academic Journal
- Accession number :
- 39121210
- Full Text :
- https://doi.org/10.1002/asia.202400718