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Copper-catalyzed C–P cross-coupling of secondary phosphines with (hetero)aromatic bromide

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Abstract

A novel and convenient approach to the synthesis of various tertiary phosphines via a copper-catalyzed cross-coupling of (hetero)aromatic bromide with secondary phosphines has been developed. The reaction employs cheap copper as the catalyst, 2,6-bis(N-methylaminomethyl)pyridine (L4) as a perfect ligand and KOtBu as a base; all reactions are carried out under argon atmosphere. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields. Moreover, ten new tertiary phosphines were first reported in this process.

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Acknowledgements

The authors gratefully acknowledge the financial support from Hebei Chemical and Pharmaceutical College. The authors are thankful to Hebei University of Science and Technology for elemental, 13C NMR, 1H NMR, 19F NMR, and 31P NMR analysis.

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  1. Chun-Jing Li and Jing Lü contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry and Environmental Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang, 050026, China

    Chun-Jing Li, Jing Lü, Zhi-Xun Zhang, Kun Zhou, Yan Li & Guang-Hui Qi

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  1. Chun-Jing Li
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Correspondence to Chun-Jing Li or Jing Lü.

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Li, CJ., Lü, J., Zhang, ZX. et al. Copper-catalyzed C–P cross-coupling of secondary phosphines with (hetero)aromatic bromide. Res Chem Intermed 44, 4547–4562 (2018). https://doi.org/10.1007/s11164-018-3403-3

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