Journal
MOLECULES
Volume 24, Issue 3, Pages -Publisher
MDPI
DOI: 10.3390/molecules24030459
Keywords
amides; C-N sigma bond cleavage; sodium; crown ether
Funding
- National Key Research and Development Plan of China [2017YFD0200504]
- National Natural Science Foundation of China [21602248, 21711530213]
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Functionalization of amide bond via the cleavage of a non-carbonyl, C-N sigma bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N sigma 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.
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