Journal
ACS CATALYSIS
Volume 11, Issue 12, Pages 7126-7131Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01901
Keywords
alpha-C-H amidation; nitrene intermediate; imidazole; iridium catalyst; dioxazolone
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Funding
- MEXT [17H06091]
- Grants-in-Aid for Scientific Research [17H06091] Funding Source: KAKEN
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The Ir(III)-catalyzed direct alpha-C-H amidation of imidazole-masked aliphatic carboxylic acids with dioxazolones was successfully achieved, with the key role of the imidazole moiety as a directing group. The products can be easily converted to esters and amides, and the reaction demonstrated a broad substrate scope. Investigating the reaction mechanism led to the proposal of an iridium nitrene intermediate.
The Ir(III)-catalyzed direct alpha-C-H amidation of imidazole-masked aliphatic carboxylic acids with dioxazolones is reported. The presence of an imidazole moiety as a directing group is a key to the success of the reaction. The products can be easily converted to esters and amides in a simple procedure. The reaction shows a broad substrate scope for various substituted 2-acylimidazoles, as well as a variety of dioxazolone derivatives with important functional groups being tolerated. The reaction mechanism was investigated by deuterium-labeling experiments, Hammett plots, NMR, and FAB-MS, and we propose the generation of an iridium nitrene intermediate.
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