Three-Component Reaction of Triphenylphosphine, Dimethyl Acetylenedicarboxylate, and Aldehyde Benzoylhydrazones: An Efficient One-Pot Synthesis of Stable Phosphorus Ylides

Abstract

Protonation of the reactive 1:1 intermediate produced in the reaction between dimethyl acetylenedicarboxylate and triphenylphosphine by benzoylhydrazones leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the NH acid to produce highly fanctionalized, salt-free phosphorus ylides in excellent yields.

Keywords:

• Benzoylhydrazones
• dimethyl acetylenedicarboxylate
• NH acids
• phosphorus ylides
• triphenylphosphine