Popular since the early 1900s, the 1,4-addition of Michael donors to activated π-systems (called Michael acceptors) to form new C-C bonds is known as the Michael addition or reaction. With the help of a base, the donor is converted to an enolate ion, which attacks the Michael acceptor. When a full equivalent of base is used, the (anion) product can further react with various electrophiles. Other processes such as 1,2-addition or self-condensation may compete with the desired 1,4-addtion, but the use of additives and the careful selection of the reaction medium can limit these undesired reactions.
- Reagents: Base (Piperidine, NEt3, NaOH, KOH, NaOEt, KOt-Bu), Protic or Aprotic Solvent
- Reactant: Michael Donor (Nucleophilic Enolate Ion Derived from an Aldehyde, Ketone, Nitrile, β-Dicarbonyl Compound, or Heteroatom, etc.), Michael Acceptor (α,β-Unsaturated System or Electron Deficient Double Bond or Triple Bond)
- Product: Michael Adduct
- Type of Reaction: Carbonyl Condensation
- Bond Formation: C-C
Mechanism
Top Citations
Original Paper
Related Reactions
- Robinson Annulation
Related Compounds
- Michael Donor
- Michael Acceptor
