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Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.


ABSTRACT: A novel direct transformation of aliphatic terminal alkynes to alkenyl nitriles through the incorporation of a nitrogen atom into the simple hydrocarbons has been reported. The usage of inexpensive copper catalyst, O2 as the sole oxidant, broad substrate scope as well as feasibility for "late-stage modification" make this protocol very promising. Mechanistic studies including DFT calculation demonstrate a novel 1,2-hydride shift process for this novel nitrogenation reaction.

SUBMITTER: Huang X 

PROVIDER: S-EPMC6054104 | biostudies-other | 2015 Nov

REPOSITORIES: biostudies-other

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Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles <i>via</i> aerobic oxidative N-incorporation.

Huang Xiaoqiang X   Li Xinyao X   Jiao Ning N  

Chemical science 20150720 11


A novel direct transformation of aliphatic terminal alkynes to alkenyl nitriles through the incorporation of a nitrogen atom into the simple hydrocarbons has been reported. The usage of inexpensive copper catalyst, O<sub>2</sub> as the sole oxidant, broad substrate scope as well as feasibility for "late-stage modification" make this protocol very promising. Mechanistic studies including DFT calculation demonstrate a novel 1,2-hydride shift process for this novel nitrogenation reaction. ...[more]

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