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Microwave-assisted aqueous Suzuki coupling reactions catalyzed by ionic palladium(II) complexes

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Abstract

Suzuki coupling is one of the most powerful methods for the synthesis of biaryls. We have prepared and characterized a series of unsymmetrical sulfonated water-soluble Pd(II)-pyridyl imine complexes and investigated them as catalysts for the Suzuki cross-coupling reaction in water under microwave irradiation. The compounds proved to be effective catalysts.

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Notes

  1. (1)Biphenyl δ 7.48–7.46 (m, 4H), 7.31–7.26 (m, 4H), 7.21–7.18 (m, 2H). (2) 4-Methylbiphenyl δ 7.56 (d, 2H, J = 7.9 Hz), 7.41 (d, 2H, J = 8.0 Hz), 7.33 (t, 2H, J = 7.5 Hz), 7.19 (t, 1H, J = 8.6 Hz), 7.11 (d, 2H, J = 7.4 Hz), 2.29 (s, 3H).(3) 2-Methylbiphenyl δ 7.41–7.33 (m, 2H), 7.31–7.29 (m, 3H), 7.27–7.21 (m, 4H), 2.19 (s, 3H).(4) 4-acetylbiphenyl δ 8.01 (d, 2H, J = 8.1 Hz), 7.61 (d, 2H, J = 8.8 Hz), 7.59 (d, 2H, J = 8.6 Hz), 7.55–7.34/m, 3H), 2.61 (s, 3H).(5) 4-methoxybiphenyl δ 7.51–7.48 (m, 4H), 7.41 (t, 2H, J = 6.9 Hz), 7.21 (t, 2H, J = 7.9 Hz), 6.88 (d, 2H, J = 8.9 Hz), 3.77 (s, 3H).(6) 2,6-dimethylbiphenyl δ 7.51 (d, 2H, J = 6.9 Hz), 7.39 (m, 2H), 7.11 (m, 1H), 6.91 (m, 3H), 2.41 (s, 6H). (7) 4-nitrobiphenyl δ 8.25 (s, 1H), 8.03 (d, 1H, J = 7.9 Hz), 7.86 (d, 1H, J = 7.6 Hz), 7.31 - 7.24 (m, 3H), 7.19–7.11 (m, 3H).(8) 4-Methyl-4′ methylbiphenyl δ 7.53 (d, 4H, J = 7.7 Hz), 7.14 (d, 4H, J = 8.1 Hz). (9) 4-Methyl-2′ methylbiphenyl δ 7.41 (d, 3H, J = 7.7 Hz), 7.09 (m, 5H), 2.28 (s, 6H). (10) 4-chloro-4-methoxybiphenyl δ 7.49–7.43 (m, 4H), 7.32 (d, 2H, J = 8.6 Hz), 6.73 (d, 2H, J = 8.5 Hz), 3.77 (s, 3H). (11) 4-Hidroxybiphenyl δ 7.48 (d, 2H, J = 6.9 Hz), 7.36–7.29 (m, 5H), 6.71 (d, 2H, J = 7.3 Hz), 5.32 (s, 1H, br). (12) 4-acetylbiphenyl δ10.09 (s, 1 h, br), 8.14 (d, 2H, J = 7.9 Hz, 7.74 (d, 2H, J = 8.3 Hz), 7.54 (m, 2H), 7.23 (m, 3H). (13) 2-methyl-4-benzoicacid δ 10.09 (s, 1H), 8.14 (d, 2H, J = 7.9 Hz), 7.74 (d, 2H, J = 8.3 Hz), 7.54 (m, 2H), 7.23 (m, 3H). (14) 4-Chlorobiphenyl δ 7.55–7.32 (m, 9H).

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Acknowledgments

This work was supported by Research Board of Zonguldak Karaelmas University (BAP-2011-10-03-011 and BAP-2011-10-03-012).

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  1. Department of Chemistry, Science and Letters Faculty , Zonguldak Karaelmas University, 67100, Zonguldak, Turkey

    M. Emre Hanhan & Yetkin Senemoglu

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  1. M. Emre Hanhan
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  2. Yetkin Senemoglu
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Correspondence to M. Emre Hanhan.

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Hanhan, M.E., Senemoglu, Y. Microwave-assisted aqueous Suzuki coupling reactions catalyzed by ionic palladium(II) complexes. Transition Met Chem 37, 109–116 (2012). https://doi.org/10.1007/s11243-011-9564-1

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