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

Molecules

College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China.

Published: January 2019

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 -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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6384560PMC
http://dx.doi.org/10.3390/molecules24030459DOI Listing

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