A novel 4-aminoantipyrine-Pd(II) complex catalyzes Suzuki-Miyaura cross-coupling reactions of aryl halides.

Claudia Araceli Contreras-Celedón,José A Rincón-Medina,Luis Chacón-García,Darío Mendoza-Rayo

doi:10.3762/bjoc.10.299

Abstract

A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under mild reaction conditions. Good to excellent product yields from the cross-coupling reaction can be achieved when the reaction is carried out in ethanol, in the open air, using low loading of 4-AAP–Pd(II) as a precatalyst, and in the presence of aqueous K2CO3 as the base. A variety of functional groups are tolerated.

Highlights

The sp2–sp2 carbon–carbon bond formation through crosscoupling reactions catalyzed by metal complexes has emerged as a powerful tool in organic synthesis [1,2,3,4,5,6]
We report the synthesis of the new 4-aminoantipyrine–Pd(II) complex [4-AAP–Pd(II)] by mixing Li2PdCl4, 4-aminoantipyrine in presence of NaOAc in MeOH at room temperature, and its performance as catalysts in SM crosscoupling reaction of structurally different aryl halides with phenylboronic acids
The synthesis of the 4-APP–Pd(II) complex was carried out using a convenient one-pot procedure, as reported in the literature for other ligands [22], by combining Li2PdCl4, 4-AAP and NaOAc in methanol at room temperature (Scheme 1)

Summary

Introduction

The sp2–sp2 carbon–carbon bond formation through crosscoupling reactions catalyzed by metal complexes has emerged as a powerful tool in organic synthesis [1,2,3,4,5,6]. We report the synthesis of the new 4-aminoantipyrine–Pd(II) complex [4-AAP–Pd(II)] by mixing Li2PdCl4, 4-aminoantipyrine in presence of NaOAc in MeOH at room temperature, and its performance as catalysts in SM crosscoupling reaction of structurally different aryl halides with phenylboronic acids.

Results

Conclusion