Cerium(III) triflate deprotects p-methoxybenzyl ethers of simple alcohols better than the cerium(III) chloride/sodium iodide system. It can be used in 1% m instead of equimolecular amounts, giving better yields. Aromatic alcohols rearrange, but the addition of a scavenger overcomes this drawback. Unfortunately, unsaturated alcohols are deprotected with decomposition, probably due to side electrophilic additions to double bonds. A comparison between the mechanisms of cerium triflate and cerium chloride is reported.
Cerium(III) Triflate versus Cerium (III) Chloride: Anion Dependence of Lewis Acid Behavior in the Deprotection of PMB Ethers
DALPOZZO, Renato;DE NINO, Antonio;MAIUOLO, Loredana;TAGARELLI, Antonio
2004-01-01
Abstract
Cerium(III) triflate deprotects p-methoxybenzyl ethers of simple alcohols better than the cerium(III) chloride/sodium iodide system. It can be used in 1% m instead of equimolecular amounts, giving better yields. Aromatic alcohols rearrange, but the addition of a scavenger overcomes this drawback. Unfortunately, unsaturated alcohols are deprotected with decomposition, probably due to side electrophilic additions to double bonds. A comparison between the mechanisms of cerium triflate and cerium chloride is reported.File in questo prodotto:
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