Dearomatization reaction

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]

Photochemical

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

Enzymatic
Main article: Microbial arene oxidation

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

Transition metal-asssisted

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. 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
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