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Imine as a linchpin approach for meta-C–H functionalization

Author

Listed:
  • Sukdev Bag

    (Indian Institute of Technology Bombay)

  • Sadhan Jana

    (Indian Institute of Technology Bombay)

  • Sukumar Pradhan

    (Indian Institute of Technology Bombay)

  • Suman Bhowmick

    (Indian Institute of Technology Bombay)

  • Nupur Goswami

    (Indian Institute of Technology Bombay)

  • Soumya Kumar Sinha

    (Indian Institute of Technology Bombay)

  • Debabrata Maiti

    (Indian Institute of Technology Bombay)

Abstract

Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing groups (DGs) served as ancillary ligands to ensure ortho-, meta- and para-C–H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. Here we report a temporary directing group (TDG) for meta-C–H functionalization via reversible imine formation. By overruling facile ortho-C–H bond activation by imine-N atom, a suitably designed pyrimidine-based TDG successfully delivered selective meta-C–C bond formation. Application of this temporary directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the meta position has been explored.

Suggested Citation

  • Sukdev Bag & Sadhan Jana & Sukumar Pradhan & Suman Bhowmick & Nupur Goswami & Soumya Kumar Sinha & Debabrata Maiti, 2021. "Imine as a linchpin approach for meta-C–H functionalization," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-21633-2
    DOI: 10.1038/s41467-021-21633-2
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    Cited by:

    1. Bishal Dutta & Mayank Mahajan & Animesh Ghosh & Maciej Dajek & Rafal Kowalczyk & Bhaskar Mondal & Haibo Ge & Debabrata Maiti, 2024. "Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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