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Kang, H. Organocatalysis. Encyclopedia. Available online: https://encyclopedia.pub/entry/60370 (accessed on 03 October 2026).
Kang H. Organocatalysis. Encyclopedia. Available at: https://encyclopedia.pub/entry/60370. Accessed October 03, 2026.
Kang, Helena. "Organocatalysis" Encyclopedia, https://encyclopedia.pub/entry/60370 (accessed October 03, 2026).
Kang, H. (2026, September 23). Organocatalysis. In Encyclopedia. https://encyclopedia.pub/entry/60370
Kang, Helena. "Organocatalysis." Encyclopedia. Web. 23 September, 2026.
Organocatalysis
Edit

Organocatalysis is the acceleration of a chemical transformation by a small organic molecule that is not a metal complex and is regenerated during the catalytic cycle [1][2]. In advanced synthetic organic chemistry the concept is bounded by the exclusive use of organic compounds—typically amines, phosphoric acids, N-heterocyclic carbenes, or phosphines—as the catalytic species, thereby excluding transition-metal catalysis and biocatalysis as the primary mode of activation [2][3]. Essential features are a defined activation mode (enamine, iminium, Brønsted-acid, nucleophilic, or carbene umpolung), turnover of the organic catalyst, and, in asymmetric organocatalysis, a chiral catalyst that differentiates prochiral faces of the substrate [2]. N-Heterocyclic carbenes operate by forming covalent Breslow-type intermediates that invert the polarity of carbonyl carbon atoms [1]. Phosphine organocatalysts add to electron-deficient π-systems to generate zwitterionic intermediates that mediate a range of annulations and substitutions [4]. Dual manifolds that merge a photoredox cycle with an organocatalytic cycle remain organocatalytic with respect to the bond-forming activation of the organic substrate [2]. The concept is distinguished from ligand-assisted metal catalysis, in which the organic molecule is not itself the catalytic center.

organocatalysis enamine activation N-heterocyclic carbene asymmetric catalysis

References

  1. Dieter Enders; Oliver Niemeier; Alexander Henseler; Organocatalysis by N-Heterocyclic Carbenes. Chem. Rev. 2007, 107, 5606-5655. [CrossRef]
  2. David W. C. MacMillan; The advent and development of organocatalysis. Nature 2008, 455, 304-308. [CrossRef]
  3. Peter I. Dalko; Lionel Moisan; In the Golden Age of Organocatalysis. Angew. Chem. Int. Ed. 2004, 43, 5138-5175. [CrossRef]
  4. Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon; Phosphine Organocatalysis. Chem. Rev. 2018, 118, 10049-10293. [CrossRef]
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Subjects: Chemistry, Organic
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Update Date: 23 Sep 2026
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