Progress in Selective Construction of Functional Aromatics with Cyclohexanone

Abstract

Cyclohexanone, a cheap and important organic chemical material with polar active carbonyl group, can construct many functional materials via nucleophilic addition with nucleophiles and subsequent transformation. In addition, the methylene group in the ortho-position of carbonyl group also exhibits good reactivity. Therefore, cyclohexanone can be used as a versatile C2 source for cycloaddition reaction providing various aromatic compounds via subsequent dehydroaromatization. The cyclohexanone involved reactions to chemoselectively produce monosubstituted aromatics, polysubstituted aromatics and heterocyclic aromatics is discussed. The addition reactions and further dehydroaromatization of cyclohexanone with nucleophiles such aldehydes, ketones, aromatic amines, thiophenols and unsaturated hydrocarbons are discussed in detail as well. The environmentally benign synthesis of aromatic functional molecules with cyclohexanone is prospected at the end of this review.