A Reusable Palladium/Cationic 2,2′-Bipyridyl System-Catalyzed Double Mizoroki-Heck Reaction in Water

Yu-Chi Chen,Chien-Chi Wu,Wei-Ting Liao,Fu-Yu Tsai,Ling-Jun Liu

doi:10.3390/catal7060177

Yu-Chi Chen, Chien-Chi Wu + Show 3 more

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https://doi.org/10.3390/catal7060177

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Abstract

A reusable PdCl2(NH3)2/cationic 2,2′-bipyridyl system was used to catalyze the double Mizoroki-Heck reaction of aryl iodides with electron-deficient alkenes in water in the absence of inert gas, giving β,β-diarylated carbonyl derivatives in good to excellent yields. The formation of unsymmetrical β,β-diarylated alkenes were also studied by coupling aryl iodides with the corresponding aryl-substituted α,β-unsaturated carbonyl compounds. This water-soluble catalyst can be swiftly separated from the organic layer using simple extraction for the further reuse, and, thus, makes it an operationally-simple and environmentally-benign procedure.

Highlights

Supported Pd complexes have been used as catalysts for β,β-double arylation of α-olefins
We have recently reported that the PdCl2 (NH3 )2 /cationic 2,20 -bipyridyl catalytic system can very valuable to approach the goal of practical application
Results andAsDiscussion shown in Entry 1 of Table 1, with the treatment of iodobenzene 1a (2.5 mmol) with n-butyl acrylate 2a (1.0 mmol), in the presence of PdCl2(NH3)2/cationic 2,2′-bipyridyl (1 mol %) and Bu3N

Summary

Introduction

The formation of unsymmetrical β,β-diarylated alkenes were studied by coupling aryl iodides with the corresponding aryl-substituted α,β-unsaturated carbonyl compounds. This water-soluble catalyst can be swiftly separated from the organic layer using simple extraction for the further reuse, and, makes it an operationally-simple and environmentally-benign procedure. Transition-metal-catalyzed β,β-double arylation of α-olefins is one of the most straightforward and common routes, in modern organic synthesis, to synthesize β,β-diaryl substituted alkenes. Palladium-catalyzed double Mizoroki-Heck coupling of aryl halides with olefins might be the most convenient method to fulfill the formation of β,β-diaryl substituted alkenes, due to the use of low catalyst loading and a large variety of reactants, which are commercial available.

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