Nagata reaction

What is Nagata reaction?

In 1962, Nagata et al. reported the Nagata reaction, which involves the conjugate hydrocyanation of an α,β-unsaturated carbonyl compound using diethylaluminum cyanide or the combination of hydrogen cyanide and diethylaluminum chloride (or triethylaluminum) in an inert solvent such as ether, THF, or benzene (see list of acronyms). The reaction is named after Nagata due to his contribution to its development.

Nagata reaction - general reaction scheme
Nagata reaction

R1, R2 = H, alkyl, aryl

Although the enol intermediate in a conjugate addition can be trapped in some cases, it is not always possible, and further reactions such as with bromine may be necessary. Additionally, the product of the reaction can vary depending on the solvent used and steric hindrance can prevent the reaction from occurring in some cases. The Nagata reaction has been extended to include the hydrocyanation of an isolated carbonyl group of β-keto sulfoxide and the hydrocyanation of epoxide functionality through the cleavage of the epoxide ring of an α-carbonyl epoxide.

References

Nagata, W., Yoshioka, M., and Hirai, S. (1962). Eine neue hydrocyanierungs-methode. Tetrahedron Letters, 3(11), 461-466. https://doi.org/10.1016/S0040-4039(00)70493-X

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