Copper-catalyzed aerobic nitrogen-migration cyanation and oxygenation of unsaturated ketoximes via the CC bond cleavage: facile access to 4-oxobutanenitriles,Organic Chemistry Frontiers

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Copper-catalyzed aerobic nitrogen-migration cyanation and oxygenation of unsaturated ketoximes via the CC bond cleavage: facile access to 4-oxobutanenitriles
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-10-29 , DOI: 10.1039/d2qo01553f
Xiao-Dong Liu _{1,

2} , Yang Li ₂ , Ming Hu _{1,

2} , Qiu-An Wang ₁ , Jin-Heng Li _{1,

2,

3,

4}

Affiliation

A new copper-catalyzed aerobic synthesis of 4-oxobutanenitriles by the nitrogen-migration cyanation and oxygenation of γ,δ-unsaturated ketoximes at room temperature is developed. By means of a copper(0) powder catalyst, the nitrogen-migration cyanation and oxygenation of unsaturated ketoximes with O₂ via a radical intramolecular 5-exo-trig cyclization, C [double bond, length as m-dash]

C double bond cleavage and ring-opening process efficiently execute to assemble 4-oxobutanenitriles. Mechanistic studies indicate that these processes include radicals initiating the reaction from the oxime side and the superoxide radical formation.

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