The Study of Catalysis Mechanism in “Copper- and Ligand-Free” Sonogashira Reaction Using the Analysis of Phase Trajectories

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

doi:10.31857/S0453881123040068

The Study of Catalysis Mechanism in “Copper- and Ligand-Free” Sonogashira Reaction Using the Analysis of Phase Trajectories

Authors: Larina E.V.¹, Kurokhtina A.A.¹, Lagoda N.A.¹, Grigoryeva T.A.¹, Schmidt A.F.¹
Affiliations:
1. Irkutsk State University, Chemical Department
Issue: Vol 64, No 4 (2023)
Pages: 428-436
Section: 7-я Международная школа-конференция молодых ученых “Катализ: от науки к промышленности”
URL: https://stomuniver.ru/0453-8811/article/view/660302
DOI: https://doi.org/10.31857/S0453881123040068
EDN: https://elibrary.ru/RQZGXZ
ID: 660302

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

The results are presented on the comparative studies of the differential selectivity patterns in “copper- and ligand-free” Sonogashira reaction under so-called artificial multiroutness aimed at the distinguishing between homogeneous and heterogeneous catalysis mechanisms. Using various amounts of soluble and insoluble heterogeneous catalyst precursors resulted in the same values of the differential selectivity of competing aryl iodides, of arylacetylenes, or of the reaction products. The observed patterns conform to the hypothesis about Sonogashira reaction proceeding through homogeneous catalysis mechanism even when heterogeneous insoluble catalyst precursors are used.

Keywords

Sonogashira reaction, palladium, kinetics, differential selectivity, mechanism

References

Rayadurgam J., Sana S., Sasikumar M., Gu Q. // Org. Chem. Front. 2021. V. 8. № 2. P. 384.
Heravi M.M., Ghanbarian M., Ghalavand N., Nazari N. // Curr. Org. Chem. 2018. V. 22. № 14. P. 1420.
Martek B.A., Gazvoda M., Urankar D., Košmrlj J. // Org. Lett. 2020. V. 22. № 13. P. 4938.
Leyva-Pérez A., Oliver-Meseguer J., Rubio-Marqués P., Corma A. // Angew. Chem. Int. Ed. 2013. V. 52. № 44. P. 11554.
Djakovitch L., Rollet P. // Adv. Synth. Catal. 2004. V. 346. № 13–15. P. 1782.
Ananikov V.P., Beletskaya I.P. // Organometallics. 2012. V. 31. P. 1595.
Prima D.O., Kulikovskaya N.S., Galushko A.S., Mironenko R.M., Ananikov V.P. // Curr. Opin. Green Sustain. Chem. 2021. V. 31. P. 100502.
Eremin D.B., Ananikov V.P. // Coord. Chem. Rev. 2017. V. 346. P. 2.
Biffis A., Centomo P., del Zotto A., Zecca M. // Chem. Rev. 2018. V. 118. P. 2249.
Шмидт А.Ф., Курохтина А.А., Ларина Е.В. // Кинетика и катализ. 2012. Т. 53. № 1. С. 86. (Schmidt A.F., Kurokhtina A.A., Larina E.V. // Kinet. Catal. 2012. V. 53. P. 84.)
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.)
Excel for Scientists and Engineers: Numerical Methods. E.J. Billo. John Wiley & Sons, 2007. 480 p.
Мироненко Р.М., Бельская О.Б., Лихолобов В.А. // Российский химический журнал. Т. 62. № 1–2. С. 141. (Mironenko R.M., Belskaya O.B., Likholobov V.A. // Russ. J. Gen. Chem. 2020. V. 90. P. 532.)
Mikhaylov V.N., Sorokoumov V.N., Liakhov D.M., Tskhovrebov A.G., Balova I.A. // Catalysts. 2018. V. 8. № 4. P. 141.
Zhao X., Liu X., Zhu Y., Lu M. // Appl. Organomet. Chem. 2015. V. 29. № 10. P. 674.
Genelot M., Dufaud V., Djakovitch L. // Adv. Synth. Catal. 2013. V. 355. P. 2604.
Thathagar M.B., Kooyman P.J., Boerleider R., Jansen E., Elsevier C.J., Rothenberg G. // Adv. Synth. Catal. 2005. V. 347. № 15. P. 1965.
Dubey P., Singh A.K. // ChemistrySelect. 2020. V. 5. № 10. P. 2925.
Goncalves R.S.B., de Oliveira A.B.V., Sindra H.C., Archanjo B.S., Mendoza M.E., Carneiro L.S.A., Buarque C.D., Esteves P.M. // ChemCatChem. 2016. V. 8. № 4. P. 743.
Ezugwu C.I., Mousavi B., Asrafa A., Mehta A., Vardhan H., Verpoort F. // Catal. Sci. Technol. 2016. V. 6. № 7. P. 2050.
Kuchkina N.V., Sorokina S.A., Bykov A.V., Sulman M.G., Bronstein L.M., Shifrina Z.B. // Nanomater. 2021. V. 11. № 12. P. 3345.
Alapour S., Farahani M.D., Ramjugernath D., Koorbanally N.A., Friedrich H.B. // ACS Sustain. Chem. Eng. 2019. V.7. № 15. P. 12697.
Gholinejad M., Esmailoghli H., Khosravi F., Sansano J.M. // J. Organomet. Chem. 2022. V. 963. P. 122295.
Karami K., Abedanzadeh S., Afroomand M., Hervés P., Bayat P. // Catal. Lett. in press.
Widegren J.A., Finke R.G. // J. Mol. Catal. A: Chem. 2003. V. 198. P. 317.
Crabtree R.H. // Chem. Rev. 2012. V. 112. № 3. P. 1536.
Шмидт А.Ф., Курохтина А.А. // Кинетика и катализ. 2012. Т. 53. № 6. С. 760. (Schmidt A.F., Kurokhtina A.A. // Kinet. Catal. 2012. V. 53. P. 714.)
Köhler K., Kleist W., Pröckl S.S. // Inorg. Chem. V. 46. P. 1876.
Schmidt A.F., al Halaiqa A., Smirnov V.V. // Synlett. 2006. V.18. P. 2861.
Wussow K., Abram A., Köhler K. // Catal. Commun. 2022. V.165. P. 106441.
Finke R.G., Ozkar S. // J. Phys. Chem. C. 2019. V. 123. P. 54.
Siemsen P., Livingston R.C., Diederich F. // Angew. Chem., Int. Ed. 2000. V. 39. № 15. P. 2632.
Темкин О.Н. // Кинетика и катализ. 2012. Т. 53. С. 326. (Temkin O.N. // Kinet. Catal. 2012. V. 53. № 3. P. 313.)
Schmidt A.F., Kurokhtina A.A., Larina E.V. // Catal. Sci. Technol. 2014. V. 4. P. 3439.
Bandini M., Luque R., Budarin V., Macquarrie D.J. // Tetrahedron. 2005. V. 61. № 41. P. 9860.