Pudovik reaction

What is Pudovik reaction?

The Pudovik reaction, also known as the Pudovik addition, is a base-promoted nucleophilic addition of organophosphorus anion to alkenes or alkynes. This reaction was first reported by Pudovik in 1950 and is named after him.

Pudovik reaction - general reaction scheme - Pudovik-Abramov reaction - Pudovik addition
Pudovik reaction

Another similar addition reaction was discovered by Abramov at the same time, which involves the addition of organophosphorus compounds to activated unsaturated systems such as alkenes, alkynes, ketones, aldehydes, and imines. This reaction is generally called the Pudovik-Abramov reaction. The reaction can occur via ionic or radical mechanisms and the outcome depends on the structure of the unsaturated substrates, the phosphorus reagents, and the experimental conditions.

For instance, a catalytic amount of di-n-butylamine can remove the labile proton on the phosphorus atom (P-H) during the addition of dialkylphosphite to aldehyde, whereas solid-supported base such as Al2O3/KOH can be used for deprotonation of a series of secondary phosphines and phosphites.

References

  • Abramov, V. S., Doklady Akad. Nauk. SSSR, 1950, 73, 487
  • Pudovik, A. N., Doklady Akad. Nauk. SSSR, 1950, 73, 499
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