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Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions

College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China
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Molecules 2019, 24(3), 459; https://doi.org/10.3390/molecules24030459
Received: 6 December 2018 / Revised: 15 January 2019 / Accepted: 16 January 2019 / Published: 28 January 2019
(This article belongs to the Special Issue Amide Bond Activation)
Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides. View Full-Text
Keywords: amides; C-N σ bond cleavage; sodium; crown ether amides; C-N σ bond cleavage; sodium; crown ether
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MDPI and ACS Style

Li, H.; Lai, Z.; Adijiang, A.; Zhao, H.; An, J. Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions. Molecules 2019, 24, 459.

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