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

Full Text: HTML

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 ...

Related Articles:

Stereoselective Synthesis of Nipecotic Acid Derivatives via Palladium-Catalyzed Decarboxylative Cyclization of γ-Methylidene-δ-valerolactones with Imines

[Shintani, Ryo; Murakami, Masataka; Hayashi, Tamio Organic Letters, 2009 , vol. 11, # 2 p. 457 - 459]

A facile one-pot benzylation of sodium enolates using trifluoromethanesulfonic anhydride and diphenyl sulfoxide

[Takuwa, Tomofumi; Minowa, Tomofumi; Fujisawa, Hidehiko; Mukaiyama, Teruaki Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 5 p. 476 - 480]

Direct conversion of α, β-unsaturated nitriles into cyanohydrins using Mn (dpm) 3 catalyst, dioxygen and phenylsilane

[Magnus, Philip; Scott, David A.; Fielding, Mark R. Tetrahedron Letters, 2001 , vol. 42, # 25 p. 4127 - 4129]

Probing Persistent Intramolecular C− H··· X (X= O, S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrum's Acid Derivatives

[Fillion, Eric; Wilsily, Ashraf; Fishlock, Dan Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1259 - 1267]

Sequential One-Pot Combination of Multireactions through Multicatalysis: A General Approach to Rapid Assembly of Functionalized Push− Pull Olefins, Phenols, and …

[Ramachary, Dhevalapally B.; Venkaiah, Chintalapudi; Reddy, Y. Vijayendar; Kishor, Mamillapalli Organic and Biomolecular Chemistry, 2009 , vol. 7, # 10 p. 2053 - 2062]

More Articles...