Dearomatization reaction
Chemical reaction
From Wikipedia, the free encyclopedia
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
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]