Distinguishing between Linear and Non-Linear (Cooperative) Substrate Activation Mechanisms in the Sonogashira Reaction under “Ligand-Free” and “Copper-Free” Conditions

E. V. Larina; Ларина Е. В.; A. A. Kurokhtina; Курохтина А. А.; N. A. Lagoda; Лагода Н. А.; A. F. Schmidt; Шмидт А. Ф.

doi:10.31857/S0453881123060102

Distinguishing between Linear and Non-Linear (Cooperative) Substrate Activation Mechanisms in the Sonogashira Reaction under “Ligand-Free” and “Copper-Free” Conditions

Autores: Larina E.V.¹, Kurokhtina A.A.¹, Lagoda N.A.¹, Schmidt A.F.¹
Afiliações:
1. Irkutsk State University, Chemical Department
Edição: Volume 64, Nº 6 (2023)
Páginas: 737-748
Seção: ARTICLES
URL: https://stomuniver.ru/0453-8811/article/view/660310
DOI: https://doi.org/10.31857/S0453881123060102
EDN: https://elibrary.ru/KUKDLB
ID: 660310

Citar

Texto integral

Acesso aberto
Acesso é fechado

Acesso está concedido
Acesso é fechado

Somente assinantes

Resumo
Sobre autores
Bibliografia
Arquivos suplementares
Estatísticas

Resumo

The results are presented on the comparative studies of the differential selectivity patterns in the Sonogashira reaction with a pair of competing aryl acetylenes in the “ligand-free” and “copper-free” conditions when varying the nature and concentration of aryl halides and base. The revealed sensitivity of the differential selectivity of competing aryl acetylenes to aryl halide nature unambiguously indicated that the substrates were activated through linear mechanism from kinetic view. An absence of any influence of the nature and concentration of the base on the differential selectivity of competing aryl acetylenes indicated the irreversible character of the step of their activation.

Palavras-chave

Sonogashira reaction, Cu- and ligand-free conditions, palladium, mechanism, kinetics, differential selectivity

Bibliografia

Rayadurgam J., Sana S., Sasikumar M., Gu Q. // Org. Chem. Front. 2021. V. 8. № 2. P. 384.
Zhu X., Wang D., Huang H., Zhang X., Wang S., Zhua H. // Dye Pigment. 2019. V. 171. P. 107657.
Wang H., Li M., Liu Y., Song J., Li C., Bo Z. // J. Mater. Chem. C. 2019. V. 7. P. 819.
Buskes M.J., Blanco M.J. // Molecules. 2020. V. 25. № 15. P. 3493.
Sonogashira K. // J. Organomet. Chem. 2002. V. 653. № 1–2. P. 46.
Dodson J.R., Hunt A.J., Parker H.L., Yang Y., Clark J.H. // Chem. Eng. Process. 2012. V. 51. P. 69.
Siemsen P., Livingston R.C., Diederich F. // Angew. Chem. Int. Ed. 2000. V. 39. P. 2632.
Mohajer F., Heravi M.M., Zadsirjan V., Poormohammad N. // RSC Adv. 2021. V. 11. № 12. P. 6885.
Chinchilla R., Nájera C. // Chem. Soc. Rev. 2011. V. 40. № 10. P. 5084.
Martek B.A., Gazvoda M., Urankar D., Košmrlj J. // Org. Lett. 2020. V. 22. № 13. P. 4938.
Bakherad M. // Appl. Organomet. Chem. 2013. V. 27. № 3. P. 125.
Urgaonkar S., Verkade J.G. // J. Org. Chem. 2004. V. 69. № 17. P. 5752.
Hong K., Sajjadi M., Suh J.M., Zhang K., Nasrollahzadeh M., Jang H.W., Varma R.S., Shokouhimehr M. // ACS Appl. Nano Mater. 2020. V. 3. № 3. P. 2070.
Sarmah M., Dewan A., Thakur A.J., Bora U. // Tetrahedron Lett. 2016. V. 57. № 8. P. 914.
Gogoi A., Dewan A., Bora U. // RSC Adv. 2015. V. 5. № 1. P. 16.
Cassar L. // J. Organomet. Chem. 1975. V. 93. P. 253.
Dieck H.A., Heck F.R. // J. Organomet. Chem. 1975. V. 93. P. 259.
García-Melchor M., Pacheco M.C., Nájera C., Lledós A., Ujaque G. // ACS Catal. 2012. V. 2. № 1. P. 135.
Ljungdahl T., Bennur T., Dallas A., Emtenäs H., Mårtensson J. // Organometallics. 2008. V. 27. № 11. P. 2490.
Gazvoda M., Virant M., Pinter B., Košmrlj J. // Nature Commun. 2018. V. 9. № 1. P. 1.
Dubey P., Singh A.K. // ChemistrySelect. 2020. V. 5. № 10. P. 2925.
Schmidt A.F., Kurokhtina A.A., Larina E.V., Vidyaeva E.V., Schmidt E.Y., Lagoda N.A. // ChemCatChem. 2020. V. 12. № 21. P. 5523.
Schmidt A.F., Kurokhtina A.A., Larina E.V., Vidyaeva E.V., Lagoda N.A. // Mol. Catal. 2021. V. 499. P. 111321.
Курохтина А.А., Ларина Е.В., Лагода Н.А., Шмидт А.Ф. // Кинетика и Катализ. 2022. Т. 63. С. 614. (Kurokhtina A.A., Larina E.V., Lagoda N.A., Schmidt A.F. // Kinet. Catal. 2022. V. 63. P. 543.)
Excel for Scientists and Engineers: Numerical Methods. 2nd Ed. E.J. Billo. John Wiley & Sons, 2007. 480 p.
Мироненко Р.М., Бельская О.Б., Лихолобов В.А. // Российский химический журнал. 2019. Т. 62. № 1–2. С. 141. (Mironenko R.M., Belskaya O.B., Likholobov V.A. // Rus. J. Gen. Chem. 2020. V. 90. P. 532.)
Biffis A., Centomo P., del Zotto A., Zecca M. // Chem. Rev. 2018. V. 118. P. 2249.
Meek S.J., Pitman C.L., Miller A.J.M. // J. Chem Educ. 2016. V. 93. № 2. P. 275.
Tan Y., Barrios-Landeros F., Hartwig J.F. // J. Am. Chem. Soc. 2012. V. 134. P. 3683.
Schmidt A.F., Kurokhtina A.A., Larina E.V. // Catal. Sci. Technol. 2014. V. 4. P. 3439.
Schmidt A.F., Kurokhtina A.A., Larina E.V., Vidyaeva E.V., Lagoda N.A. // Mol. Catal. 2022. V. 524. P. 112260.
Шмидт А.Ф., Курохтина А.А., Ларина Е.В. // Кинетика и катализ. 2019. Т. 60. № 5. С. 555. (Schmidt A.F., Kurokhtina A.A., Larina E.V. // Kinet. Catal. 2019. V. 60. P. 551.)
Темкин О.Н. // Кинетика и катализ. 2012. Т. 53. С. 326. (Temkin O.N. // Kinet. Catal. 2012. V. 53. P. 313.)
Toledo A., Funes-ardoiz I., Maseras F., Albéniz A.C. // ACS Catal. 2018. V. 8. № 8. P. 7495.
de Vries A.H.M., Mulders J.M.C.A., Mommers J.H.M., Henderickx H.J.W., de Vries J.G. // Org. Lett. 2003. V. 5. P. 3285.
Eremin D.B., Ananikov V.P. // Coord. Chem. Rev. 2017.V. 346. P. 2.
Schmidt A.F., al Halaiqa A., Smirnov V.V. // Synlett. 2006. V. 18. P. 2861.
Finney E.E., Finke R.G. // Ind. Eng. Chem. Res. 2017. V. 56. № 37. P. 10271.
Finke R.G., Ozkar S. // J. Phys. Chem. C. 2019. V. 123. P. 54.
Köhler K., Kleist W., Pröckl S.S. // Inorg. Chem. V. 46. P. 1876.