Usage:

For the synthesis of heterocycles

Catalytic amounts of aqueous CAN allow the efficient synthesis of quinoxaline derivatives. Quinoxalines are known for their applications as dyes, organic semiconductors, and DNA cleaving agents. These derivatives are also components in antibiotics such as echinomycin and actinomycin. The CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers provides an efficient entry into 2-methyl-1,2,3,4-tetrahydroquinolines and the corresponding quinolines obtained by their aromatization.

As a deprotection reagent

CAN is traditionally used to release organic ligands from metal carbonyls. In the process, the metal is oxidised, CO is evolved, and the organic ligand is released for further manipulation.[3] For example, with the Wulff–Dötz reaction an alkyne, carbon monoxide, and a chromium carbene are combined to form a chromium half-sandwich complex[4][5] and the phenol ligand can be isolated by mild CAN oxidation.

CAN is used to convert para-methoxybenzyl and 3,4-dimethoxybenzyl ethers, which are protecting groups for alcohols. Two equivalents of CAN are required for each equivalent of para-methoxybenzyl ether. The alcohol is released, and the para-methoxybenzyl ether converts to para-methoxybenzaldehyde. The balanced equation is as follows:

2 (NH₄)₂Ce(NO₃)₆ + H₃COC₆H₄CH₂OR + H₂O → 4 NH₄⁺ + 2 Ce³⁺ + 12 NO₃⁻ + 2 H⁺ + H₃COC₆H₄CHO + HOR