Dearomatization reaction

Last updated

A dearomatization reaction is an organic reaction in which the reactants are arenes and the products permanently lose their aromaticity. [1] It is of some importance in synthetic organic chemistry for the organic synthesis of new building blocks [1] and in total synthesis. [2] Types of carbocyclic arene dearomization include hydrogenative (Birch reduction), alkylative, photochemical, thermal, oxidative, transition metal-assisted and enzymatic. [1]

Contents

Photochemical

Examples of photochemical reactions are those between certain arenes and alkenes forming [2+2] and [2+4] cycloaddition adducts. [1]

Enzymatic

Examples of enzymes capable of arene dearomatization [3] [4] are toluene dixoyhydrogenase, naphthalene dixoyhydrogenase and benzoyl CoA reductase. [1]

Transition metal-assisted

A classic example of transition metal-assisted dearomatization is the Buchner ring expansion. [1] Catalytic asymmetric dearomatization reactions (CADA) are used in enantioselective synthesis. [5]

References

  1. 1 2 3 4 5 6 Pigge, F. C. (2015) Dearomatization Reactions, in Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds (ed J. Mortier), John Wiley & Sons, Inc, Hoboken, NJ. doi:10.1002/9781118754887.ch15
  2. ↑ Roche, S. P. and Porco, J. A. (2011), Dearomatization Strategies in the Synthesis of Complex Natural Products. Angew. Chem. Int. Ed., 50: 4068–4093. doi:10.1002/anie.201006017
  3. ↑ Anaerobic degradation of homocyclic aromatic compounds via arylcarboxyl-coenzyme A esters: organisms, strategies and key enzymes. Boll M, Löffler C, Morris BE, Kung JW. Environ Microbiol. 2014 Mar;16(3):612-27. doi:10.1111/1462-2920.12328
  4. ↑ Dearomatizing Benzene Ring Reductases Boll M. J Mol Microbiol Biotechnol 2005;10:132–142 doi:10.1159/000091560
  5. ↑ Zhuo, C.-X., Zhang, W. and You, S.-L. (2012), Catalytic Asymmetric Dearomatization Reactions. Angew. Chem. Int. Ed., 51: 12662–12686. doi:10.1002/anie.201204822
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.