Tetrahedron letters

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

M Yokogi, R Kuwano

Index: Yokogi, Masashi; Kuwano, Ryoichi Tetrahedron Letters, 2007 , vol. 48, # 35 p. 6109 - 6112

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Citation Number: 26

Abstract

The palladium complex prepared in situ from [Pd (η3-C3H5)(cod)] BF4 and bidentate phosphine DPPF was a good catalyst for the nucleophilic substitution of benzyl acetate. Significant acceleration of the palladium-catalyzed substitution was observed when an alcohol was employed as a reaction solvent. The palladium catalyst was effective for the benzylation of various stabilized carbanions, amines, and benzenesulfinate with benzylic ...

~58%

~22%

~90%

~83%

~92%

~88%

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