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Selective C−N Bond Cleavage of N‐Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents.
- Source :
-
Advanced Synthesis & Catalysis . 12/3/2019, Vol. 361 Issue 23, p5383-5391. 9p. - Publication Year :
- 2019
-
Abstract
- New multipurpose arylation/acylation/transamination reagents, N‐acylisatins, have been developed by selective 'inside‐outside' C−N bond cleavage under different catalytic conditions. As activated amides, N‐acylisatins undergo Rh‐catalyzed C−H arylation and Pd‐catalyzed acylation by cleavage outside the C−N bond, and the desired biaryls and diaryl ketones were obtained in good to excellent yields. Generally, the combination of N‐acylisatins with amines leads to a ring‐opening reaction and formation of transamination products in a predictable manner through inside C−N bond cleavage. Interestingly, treatment of N‐acylisatins with amines lead to unexpected outer‐ring transamination products when CsF is added, which shows that CsF can favor the outside C−N bond cleavage path. Notably, this work presents a new strategy for multiple chemical transformations of a single amide to achieve various products by selective C−N bond cleavage. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 361
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 140071701
- Full Text :
- https://doi.org/10.1002/adsc.201900819