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Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for γ-Lactam Formation : Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for gamma-Lactam Formation
Cited 26 time in
Web of Science
Cited 25 time in Scopus
- Authors
- Issue Date
- 2019-04
- Publisher
- American Chemical Society
- Citation
- Organic Letters, Vol.21 No.8, pp.2808-2812
- Abstract
- Described herein is the development of a new entry of acylnitrenoid precursors for gamma-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to gamma-lactams starting from the corresponding carboxylic acids.
- ISSN
- 1523-7060
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