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

作者: Larina E.V.¹, Kurokhtina A.A.¹, Lagoda N.A.¹, Schmidt A.F.¹
隶属关系:
1. Irkutsk State University, Chemical Department
期: 卷 64, 编号 6 (2023)
页面: 737-748
栏目: ARTICLES
URL: https://gynecology.orscience.ru/0453-8811/article/view/660310
DOI: https://doi.org/10.31857/S0453881123060102
EDN: https://elibrary.ru/KUKDLB
ID: 660310

如何引用文章

全文:

开放存取

##reader.subscriptionAccessGranted##
受限制的访问

订阅存取

详细
作者简介
参考
补充文件
统计

详细

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.

关键词

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

参考

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.