Synthesis 2025; 57(05): 1059-1071
DOI: 10.1055/s-0043-1775403
paper

First Example of Aryl–Hetaryl Cross-Coupling via [5,5]-Sigmatropic Rearrangement

Authors

  • Oleksandr V. Buravov

    a   Institute of Functional Materials Chemistry, State Scientific Institution ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61072, Ukraine
    b   Enamine Ltd., Winston Churchill Street 78, Kyiv 02094, Ukraine
  • Victor O. Tomak

    c   Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, Kharkiv 61022, Ukraine
  • Svitlana V. Shishkina

    a   Institute of Functional Materials Chemistry, State Scientific Institution ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61072, Ukraine
    d   Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Akademika Kukharya Street 5, Kyiv 02660, Ukraine
  • Valentyn A. Chebanov

    a   Institute of Functional Materials Chemistry, State Scientific Institution ‘Institute for Single Crystals’ of the National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61072, Ukraine
    c   Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, Kharkiv 61022, Ukraine

The authors thank the National Academy of Sciences of Ukraine for financial support (project ‘Directed synthesis, chemical transformations and properties of new nitrogen-containing heterocyclic compounds’; 0122U001857).


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Abstract

Polysubstituted furans and thiophenes with orthogonal functional groups were synthesized by a Strecker-type reaction leading to (arylaminonitriles), which underwent a [5,5]-sigmatropic rearrangement under mild conditions. The intramolecular character of the rearrangement was additionally proved.

Supporting Information



Publikationsverlauf

Eingereicht: 04. Mai 2024

Angenommen nach Revision: 28. August 2024

Artikel online veröffentlicht:
26. September 2024

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