Transition-Metal-Free Hydration of Nitriles Using Potassium tert-Butoxide under Anhydrous Conditions

Potassium tert-butoxide acts as a nucleophilic oxygen source during the hydration of nitriles to give the corresponding amides under anhydrous conditions. The reaction proceeds smoothly for a broad range of substrates under mild conditions, providing an efficient and economically affordable syntheti...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-04, Vol.80 (8), p.4148-4151
Main Authors: Midya, Ganesh Chandra, Kapat, Ajoy, Maiti, Subhadip, Dash, Jyotirmayee
Format: Article
Language:English
Subjects:
Butanols - chemistry
Catalysis
Electron Transport
Metals - chemistry
Molecular Structure
Nitriles - chemistry
Transition Elements - chemistry
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Summary:Potassium tert-butoxide acts as a nucleophilic oxygen source during the hydration of nitriles to give the corresponding amides under anhydrous conditions. The reaction proceeds smoothly for a broad range of substrates under mild conditions, providing an efficient and economically affordable synthetic route to the amides in excellent yields. This protocol does not need any transition-metal catalyst or any special experimental setup and is easily scalable to bulk scale synthesis. A single-electron-transfer radical mechanism as well as an ionic mechanism have been proposed for the hydration process.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo502752u