dearomatization reaction

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

Photochemical

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

Enzymatic

Examples of enzymes capable of arene dearomatization are toluene dixoyhydrogenase, naphthalene dixoyhydrogenase and benzoyl CoA reductase.

Transition metal-assisted

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

References

{{reflist|colwidth=50em |refs=

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}}

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}}

Dearomatizing Benzene Ring Reductases Boll M. J Mol Microbiol Biotechnol 2005;10:132–142 {{doi|10.1159/000091560}}

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}}

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}}

}}

Category:Organic reactions