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Positional isomerisation of pyridine via nitrogen transposition

Nature作者：Wonjun Choi2026年8月17日正文已收录本站
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Abstract

Positional isomers of pyridines often display distinct biological activities1,2 yet their direct interconversion remains largely inaccessible, so each isomer is typically prepared through an independent synthesis. Here we report a general strategy for pyridine positional isomerization enabled by controlled reorganization of the heteroaromatic core through sequential nitrogen insertion and deletion. N-atom transposition allows predictable translocation of preinstalled substituents without altering substituent identity. The method is broadly applicable to mono-, di-, and multisubstituted pyridines and operates across structurally complex molecular environments, providing direct access to positional isomers. This work establishes positional isomerization as a practical synthetic transformation, defining pyridine substitution patterns as mutable variables in retrosynthetic design.

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Author notes

  1. These authors contributed equally: Hyewon Ju, Jiyong Park

Authors and Affiliations

  1. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, Korea

    Wonjun Choi, Hyewon Ju & Sungwoo Hong

  2. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Korea

    Wonjun Choi, Hyewon Ju, Jiyong Park & Sungwoo Hong

Authors

  1. Wonjun Choi
  2. Hyewon Ju
  3. Jiyong Park
  4. Sungwoo Hong

Corresponding author

Correspondence to Sungwoo Hong.

Supplementary information

Supplementary Information (download PDF )

This Supplementary Information file contains the following sections: I. General information; II. Reaction optimization; III. Substrate scope; IV. Investigation of positional isomerization regioselectivity; V. Investigation of positional isomers and unsuccessful substrates; VI. Mechanistic studies; VII. Computed proposed reaction mechanism; VIII. Computational details; IX. Preparation of starting materials; X. X-ray crystallographic data; XI. References; Appendix I. Spectral Copies of 1H-, 13C- and 19F-NMR Data Obtained in this Study; Appendix II. DFT Calculation Data.

Supplementary Data (download ZIP )

This zipped folder contains the crystallographic information for compound 7bc (file name: A26002_002.cif) and the IUCr CheckCIF validation report for the crystallographic structure of compound 7bc (file name: A26002_002_checkcif.pdf).

Peer Review File (download PDF )

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Cite this article

Choi, W., Ju, H., Park, J. et al. Positional isomerisation of pyridine via nitrogen transposition. Nature (2026). https://doi.org/10.1038/s41586-026-11006-4

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  • DOI: https://doi.org/10.1038/s41586-026-11006-4