Next Article in Journal
Exploratory Cortex Metabolic Profiling Revealed the Sedative Effect of Amber in Pentylenetetrazole-Induced Epilepsy-Like Mice
Next Article in Special Issue
Fast Amide Bond Cleavage Assisted by a Secondary Amino and a Carboxyl Group—A Model for yet Unknown Peptidases?
Previous Article in Journal
Synergistic Effects of The Enhancements to Mitochondrial ROS, p53 Activation and Apoptosis Generated by Aspartame and Potassium Sorbate in HepG2 Cells
Previous Article in Special Issue
Chemistry of Bridged Lactams: Recent Developments
Open AccessCommunication

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
Author to whom correspondence should be addressed.
Molecules 2019, 24(3), 459;
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
Show Figures

Graphical abstract

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Search more from Scilit
Back to TopTop