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

Oleksandr V. Buravov; Victor O. Tomak; Svitlana V. Shishkina; Valentyn A. Chebanov

doi:10.1055/s-0043-1775403

Synthesis, Table of Contents

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

Oleksandr V. Buravov

^aInstitute 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

^bEnamine Ltd., Winston Churchill Street 78, Kyiv 02094, Ukraine

,

Victor O. Tomak

^cFaculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, Kharkiv 61022, Ukraine

,

Svitlana V. Shishkina

^aInstitute 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

^dInstitute of Organic Chemistry, National Academy of Sciences of Ukraine, Akademika Kukharya Street 5, Kyiv 02660, Ukraine

,

Valentyn A. Chebanov ∗

^aInstitute 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

^cFaculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, Kharkiv 61022, Ukraine

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Abstract

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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.

Key words

heterocycles - aminonitriles - sigmatropic rearrangement - furans - thiophenes - thiazoles

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References

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