Abstract
A new cleavage reaction of benzylethers catalyzed by copper (II) trifluoromethane- sulfonate in the presence of diacetoxyiodobenzene and p-toluene sulfonamide is described. This novel method allowed the selective cleavage of various benzyl ethers into benzylideneaniline and alcohols or phenols under mild conditions.
Highlights
The conversion of alcohols or phenols to ethers and their subsequent cleavage is very important in organic synthesis, in multi-step synthesis of complex natural products and in the manufacture of many pharmaceuticals and fine chemicals.[1]
The oxidative cleavage of benzyl ethers provides a convenient alternative to the usual reductive deprotection method
As part of our continuing study on nitrene insertions into C–H bond, 7 we explored the amidation of dibenzyl ether with PhI(OAc)2/TsNH2 catalyzed by various metal complex in dichloromethane to synthesize 1,1-N,O compounds
Summary
The conversion of alcohols or phenols to ethers and their subsequent cleavage is very important in organic synthesis, in multi-step synthesis of complex natural products and in the manufacture of many pharmaceuticals and fine chemicals.[1]. We report a mild new method for the removal of the benzyl ether protecting group through the reaction of diacetoxyiodobenzene (PhI(OAc)2) and ISSN 1551-7012 Instead of giving the desired product, when Cu(CF3SO3)[2] was used as catalyst, benzyl alcohol 2a and benzylideneaniline 3 was produced in manner of ether cleavage (Scheme 1).
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