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-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]