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Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control

Author

Listed:
  • Peng-Bo Bai

    (Lanzhou University)

  • Alastair Durie

    (University of Manchester)

  • Gang-Wei Wang

    (Lanzhou University)

  • Igor Larrosa

    (University of Manchester)

Abstract

Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta-C−H bond alkylation of aromatics bearing N-directing groups using (hetero)aromatic epoxides as alkylating agents. This method results in complete regioselectivity on both the arene as well as the epoxide coupling partners, cleaving exclusively the benzylic C−O bond. Oxetanes, which are normally unreactive, also participate as alkylating reagents under the reaction conditions. Our mechanistic studies reveal an unexpected reversible epoxide ring opening process undergoing catalyst-controlled regioselection, as key for the observed high regioselectivities.

Suggested Citation

  • Peng-Bo Bai & Alastair Durie & Gang-Wei Wang & Igor Larrosa, 2024. "Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-023-44219-6
    DOI: 10.1038/s41467-023-44219-6
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    References listed on IDEAS

    as
    1. Shangda Li & Lei Cai & Huafang Ji & Long Yang & Gang Li, 2016. "Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives," Nature Communications, Nature, vol. 7(1), pages 1-8, April.
    2. Hang Shi & Alastair N. Herron & Ying Shao & Qian Shao & Jin-Quan Yu, 2018. "Enantioselective remote meta-C–H arylation and alkylation via a chiral transient mediator," Nature, Nature, vol. 558(7711), pages 581-585, June.
    3. Xiao-Chen Wang & Wei Gong & Li-Zhen Fang & Ru-Yi Zhu & Suhua Li & Keary M. Engle & Jin-Quan Yu, 2015. "Ligand-enabled meta-C–H activation using a transient mediator," Nature, Nature, vol. 519(7543), pages 334-338, March.
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