Transition-metal-free hydration of nitriles using potassium tert-butoxide under anhydrous conditions

The Journal of Organic Chemistry
Ganesh Chandra MidyaJyotirmayee Dash

Abstract

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.

References

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Feb 12, 2014·Organic & Biomolecular Chemistry·Ganesh Chandra MidyaJyotirmayee Dash

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Citations

Dec 23, 2016·The Journal of Organic Chemistry·Tingjie YouYuanzhi Xia
Sep 10, 2015·Organic & Biomolecular Chemistry·Lixin LiuShuang-Feng Yin
Dec 2, 2017·Chemistry : a European Journal·Ritwika RayGoutam Kumar Lahiri
Aug 18, 2017·Chemistry : a European Journal·Rebeca González-FernándezRamón López
May 22, 2019·Organic & Biomolecular Chemistry·Haridas B RodeSrivari Chandrasekhar
May 18, 2019·Chemistry : a European Journal·Whalmany L OunkhamBrian J Frost
Nov 20, 2016·Angewandte Chemie·Ouidad LahtiguiAlexander J Grenning
Oct 28, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yajun SunChenjiang Liu
Oct 7, 2020·Organic & Biomolecular Chemistry·Jayashree MadasuAmit Shard
Jun 26, 2021·European Journal of Medicinal Chemistry·Shannon PecnardOlivier Provot
Nov 29, 2017·The Journal of Organic Chemistry·Santanu Ghosh, Chandan K Jana
Jun 28, 2019·The Journal of Organic Chemistry·Dripta De JoarderDilip K Maiti
Aug 10, 2018·The Journal of Organic Chemistry·Seuli ParuaNanda D Paul
Sep 28, 2021·The Journal of Organic Chemistry·Tridev GhoshJyotirmayee Dash

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