Tetrahedron Letters

Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid

S Fletcher, PT Gunning

Index: Fletcher, Steven; Gunning, Patrick T. Tetrahedron Letters, 2008 , vol. 49, # 33 p. 4817 - 4819

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Citation Number: 38

Abstract

The mild and efficient deblocking of aryl benzyl ethers with TFA is reported. Cleavage was fastest with ortho-electron-withdrawing groups on the phenolic ring, which we have attributed to a proton chelation effect, furnishing the deprotected phenols in excellent yields. The corresponding para-methoxybenzyl, allyl and iso-propyl ethers were also cleanly removed under these conditions. In addition, the selective aryl benzyl ether debenzylation ...