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Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives

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  • Shangda Li

    (State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Lei Cai

    (State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Huafang Ji

    (State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Long Yang

    (State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences)

  • Gang Li

    (State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
    Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, CAS)

Abstract

Benzoic acids are highly important structural motifs in drug molecules and natural products. Selective C–H bond functionalization of benzoic acids will provide synthetically useful tools for step-economical organic synthesis. Although direct ortho-C–H functionalizations of benzoic acids or their derivatives have been intensely studied, the ability to activate meta-C–H bond of benzoic acids or their derivatives in a general manner via transition-metal catalysis has been largely unsuccessful. Although chelation-assisted meta-C–H functionalization of electron-rich arenes was reported, chelation-assisted meta-C–H activation of electron-poor arenes such as benzoic acid derivatives remains a formidable challenge. Herein, we report a general protocol for meta-C–H olefination of benzoic acid derivatives using a nitrile-based sulfonamide template. A broad range of benzoic acid derivatives are meta-selectively olefinated using molecular oxygen as the terminal oxidant. The meta-C–H acetoxylation, product of which is further transformed at the meta-position, is also reported.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms10443
    DOI: 10.1038/ncomms10443
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    Cited by:

    1. 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.

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