A highly active palladium(II)–bis(oxazoline) catalyst for Suzuki–Miyaura,Mizoroki–Heck and sonogashira coupling reactions in aqueous dimethylformamide |
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Authors: | Mansur B Ibrahim Bassam El Ali Mohammed Fettouhi Lahcène Ouahab |
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Institution: | 1. Chemistry Department, King Fahd University of Petroleum & Minerals, Dhahran, Saudi Arabia;2. Institut Sciences Chimiques de Rennes, UMR 6226, CNRS, Université de Rennes 1, France |
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Abstract: | An efficient catalytic system based on a new palladium–bis(oxazoline) ( Pd-BOX-1 ) complex has been developed. The complex Pd-BOX-1 adopts a legless chair‐type structure where the distorted square planar PdN2Cl2] moiety and the benzene ring spacer represent the seat and the chair back, respectively. The catalytic activity of Pd-BOX-1 has been investigated in dimethylformamide–water under aerobic and mild conditions in Suzuki–Miyaura coupling reactions of arylboronic acids with aryl iodides, aryl bromides and aryl chlorides, Mizoroki–Heck coupling reactions of aryl halides with styrene derivatives, and Sonogashira coupling reactions of aryl halides with terminal alkynes. A wide range of functional groups as substituents on the arylboronic acids and aryl halides were considered. Pd-BOX-1 demonstrates exceptional air and moisture stability. Of note, the catalyst system based on Pd-BOX-1 shows high recycling ability in Suzuki–Miyaura coupling reactions in dimethylformamide–water without any loss in catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd. |
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Keywords: | palladium bis(oxazoline) Suzuki– Miyaura Mizoroki– Heck arylboronic acid aryl halides styrene derivatives reusability |
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