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General cross-coupling reactions with adaptive dynamic homogeneous catalysis

Author

Listed:
  • Indrajit Ghosh

    (Universität Regensburg)

  • Nikita Shlapakov

    (Universität Regensburg
    Russian Academy of Sciences)

  • Tobias A. Karl

    (Universität Regensburg)

  • Jonas Düker

    (Universität Regensburg)

  • Maksim Nikitin

    (Universität Regensburg)

  • Julia V. Burykina

    (Russian Academy of Sciences)

  • Valentine P. Ananikov

    (Russian Academy of Sciences)

  • Burkhard König

    (Universität Regensburg)

Abstract

Cross-coupling reactions are among the most important transformations in modern organic synthesis1–3. Although the range of reported (het)aryl halides and nucleophile coupling partners is very large considering various protocols, the reaction conditions vary considerably between compound classes, necessitating renewed case-by-case optimization of the reaction conditions4. Here we introduce adaptive dynamic homogeneous catalysis (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp2)–(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp2)–S, Se, N, P, B, O, C(sp3, sp2, sp), Si, Cl) with hundreds of synthetic examples under predictable reaction conditions. The catalytic reaction centre(s) and conditions differ from one another by the added nucleophile, or if required, a commercially available inexpensive amine base.

Suggested Citation

  • Indrajit Ghosh & Nikita Shlapakov & Tobias A. Karl & Jonas Düker & Maksim Nikitin & Julia V. Burykina & Valentine P. Ananikov & Burkhard König, 2023. "General cross-coupling reactions with adaptive dynamic homogeneous catalysis," Nature, Nature, vol. 619(7968), pages 87-93, July.
    • Handle: RePEc:nat:nature:v:619:y:2023:i:7968:d:10.1038_s41586-023-06087-4
    DOI: 10.1038/s41586-023-06087-4
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    Cited by:

    1. Jinghao Wang & Siyang Li & Caoyu Yang & Huiwen Gao & Lulu Zuo & Zhiyu Guo & Pengqi Yang & Yuheng Jiang & Jian Li & Li-Zhu Wu & Zhiyong Tang, 2024. "Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

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