Mechanistic insights into phospha–Michael reaction of tertiary phosphines with electron-deficient alkenes

ABSTRACT

The Michael-type addition of tertiary phosphines to electron-deficient alkenes is a convenient way to generate reactive phosphonium zwitterionic intermediates, which participate readily in many synthetically useful transformations. Although the synthetic usefulness of the phospha–Michael addition has been largely demonstrated, knowledge on the kinetics and mechanism of this reaction is sparse. This paper briefly summarizes the contribution of our research group to find out the mechanism of this reaction.

GRAPHICAL ABSTRACT

KEYWORDS:

• Anchimeric assistance
• conjugate addition
• rate-determining step
• solvent isotope effect
• tertiary phosphines