Michael Addition-百灵威

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

Original Paper

Michael, A. Ueber Die Addition von Natriumacetessig- Und Natriummalonsäureäthern Zu Den Aethern Ungesättigter Säuren. Journal für Praktische Chemie 1887, 35 (1), 349–356.

Top Citations

Functionalized Chiral Ionic Liquids as Highly Efficient Asymmetric Organocatalysts for Michael Addition to Nitroolefins. Angewandte Chemie International Edition 2006, 45 (19), 3093–3097.

Michael Addition Reactions in Macromolecular Design for Emerging Technologies. Progress in Polymer Science 2006, 31 (5), 487–531.

The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry. Chem. Mater. 2014,26 (1), 724-744.

Related Reactions

Robinson Annulation

Related Compounds

Michael Donor

Michael Acceptor