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

ABSTRACT: Functionalization of amide bond via the cleavage of a non-carbonyl, C-N ? bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N ? 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.

SUBMITTER: Li H

PROVIDER: S-EPMC6384560 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Li Hengzhao H Lai Zemin Z Adijiang Adila A Zhao Hongye H An Jie J

Molecules (Basel, Switzerland) 20190128 3

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 <i>N</i>-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 ame ...[more]

PMID: 30696043

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