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Catalysis of the Suzuki–Miyaura coupling reaction in water by heteroannular cyclopalladated ferrocenylimine complexes

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Abstract

Catalytic studies on the air- and moisture-stable triphenylphosphine (PPh3) adducts of heteroannular cyclopalladated ferrocenylimines [PdCl{C5H4FeC5H4CHRN=CHC4H3X}(Ph3P)] (R = H, CH3; X = S, O) indicate that they are all effective catalysts for the Suzuki–Miyaura coupling reaction of activated aryl bromides with phenylboronic acid in water under air atmosphere. Typically, using 1 mol‰ of catalyst in the presence of 1.2 equivalents of K3PO4 as base in water at 100 °C provided the corresponding biaryls in good to excellent yields. Meanwhile, the structure of [PdCl{C5H4FeC5H4CH(CH3)N=CHC4H3S}(PPh3)] has been established by the single-crystal X-ray diffraction technique. According to the crystal structure, the palladium atom is bound to the unsubstituted Cp ring, showing the four-coordinate structure typical of palladium complexes.

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Acknowledgments

We are grateful to the National Science Foundation of China (20872133), the Innovation Fund for Outstanding Scholar of Henan Province (074200510005), and the Natural Science Foundation of Henan Education Department (2009A150027) for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, 450052, Zhengzhou, People’s Republic of China

    Xue-Mei Zhao, Xin-Qi Hao, Kun-Lun Wang, Jun-Rui Liu, Mao-Ping Song & Yang-Jie Wu

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  1. Xue-Mei Zhao
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  2. Xin-Qi Hao
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  3. Kun-Lun Wang
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  4. Jun-Rui Liu
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Correspondence to Mao-Ping Song.

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Zhao, XM., Hao, XQ., Wang, KL. et al. Catalysis of the Suzuki–Miyaura coupling reaction in water by heteroannular cyclopalladated ferrocenylimine complexes. Transition Met Chem 34, 683–688 (2009). https://doi.org/10.1007/s11243-009-9248-2

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