Transformations of Pd/(N-Heterocyclic Carbene) Molecular Complexes into a Nanosized Catalytic Systems in the Mizoroki–Heck Reaction

A. Yu. Kostyukovich; Костюкович А. Ю.; E. D. Patil; Патиль Е. Д.; J. V. Burykina; Бурыкина Ю. В.; V. P. Ananikov; Анаников В. П.

doi:10.31857/S0453881123010033

Transformations of Pd/(N-Heterocyclic Carbene) Molecular Complexes into a Nanosized Catalytic Systems in the Mizoroki–Heck Reaction

作者: Kostyukovich A.Y.¹, Patil E.D.¹, Burykina J.V.¹, Ananikov V.P.¹
隶属关系:
1. Zelinsky Institute of Organic Chemistry RAS
期: 卷 64, 编号 1 (2023)
页面: 53-64
栏目: ARTICLES
URL: https://journal-vniispk.ru/0453-8811/article/view/137016
DOI: https://doi.org/10.31857/S0453881123010033
EDN: https://elibrary.ru/KGSNIQ
ID: 137016

如何引用文章

全文:

详细
作者简介
参考
补充文件
统计

详细

The mechanism of the formation of catalytic species in the practically important Mizoroki–Heck reaction, which is in demand in modern fine organic synthesis, has been studied. It has been shown that catalysts based on palladium complexes with N-heterocyclic carbene ligands are transformed into a “ligand-free” form under the conditions of the Mizoroki–Heck reaction. Molecular modeling performed using quantum chemical methods showed that these processes compete with the target reaction at three of the six stages of the catalytic cycle. The presence of catalyst transformation products in the reaction system was confirmed by methods of nuclear magnetic resonance and mass spectrometry. Important mechanistic data have been obtained for the rational design of catalytic systems for cross-coupling reactions.

关键词

Mizoroki–Heck reaction, catalysis, quantum chemical calculations, reaction mechanism

参考

Cazin C.S.J. N-Heterocyclic carbenes in transition metalcatalysis and organocatalysis. Springer Science & Business Media, 2010. 336 p. https://doi.org/10.1007/978-90-481-2866-2.
Темкин О.Н. “Золотой век” гомогенно-каталитической химии алкинов: димеризация и олигомеризация алкинов // Кинетика и катализ. 2019. Т. 60. № 6. С. 683. https://doi.org/10.1134/S0453881119060157
Díez-González S., Nolan S.P. Stereoelectronic parameters associated with N-heterocyclic carbene (NHC) ligands: a quest for understanding // Coord. Chem. Rev. 2007. V. 251. P. 874. https://doi.org/10.1016/j.ccr.2006.10.004
Jacobsen H., Correa A., Poater A., Costabile C., Cavallo L. Understanding the M-(NHC) (NHC = N-heterocyclic carbene) bond // Coord. Chem. Rev. 2009. V. 253. P. 687. https://doi.org/10.1016/j.ccr.2008.06.006
Van Leeuwen P.W. Decomposition pathways of homogeneous catalysts // Appl. Catal. A: Gen. 2001. V. 212. P. 61. https://doi.org/10.1016/S0926-860X(00)00844-9
Magill A.M., Yates B.F., Cavell K.J., Skelton B.W., White A.H. Synthesis of N-heterocyclic carbene palladium (II) bis-phosphine complexes and their decomposition in the presence of aryl halides // Dalton Trans. 2007. V. 31. P. 3398. https://doi.org/10.1039/B706053J
Курохтина А.А., Ларина Е.В., Лагода Н.А., Шмидт А.Ф. Роль процессов формирования–дезактивации катализатора и свидетельства нелинейного механизма в реакции Мицороки–Хека с арилхлоридами // Кинетика и катализ. 2022. Т. 63. № 5. С. 614–627. https://doi.org/10.31857/S0453881122050070
Ларина Е.В., Курохтина А.А., Лагода Н.А., Шмидт А.Ф. Влияние добавок солей и фосфинов на состав активных комплексов палладия в реакции Мицороки–Хека с ангидридами ароматических кислот // Кинетика и катализ. 2022. Т. 63. № 2. С. 234. https://doi.org/10.31857/S0453881122020058
Eremin D.B., Boiko D.A., Kostyukovich A.Yu., Burykina J.V., Denisova E.A., Anania M., Martens J., Berden G., Oomens J., Roithová J., Ananikov V.P. Mechanistic study of Pd/NHC-catalyzed sonogashira reaction: discovery of NHC-ethynyl coupling process // Chem. Eur. J. 2020. V. 26. P. 15672. https://doi.org/10.1002/chem.202003533
Denisova E.A., Eremin D.B., Gordeev E.G., Tsedilin A.M., Ananikov V.P. Addressing reversibility of R-NHC coupling on palladium: is nano-to-molecular transition possible for the Pd/NHC System? // Inorg. Chem. 2019. V. 58. P. 12218. https://doi.org/10.1021/acs.inorgchem.9b01630
Chernyshev V.M., Khazipov O.V., Shevchenko M.A., Chernenko A.Y., Astakhov A.V., Eremin D.B., Pasyukov D.V., Kashin A.S., Ananikov V.P. Revealing the unusual role of bases in activation/deactivation of catalytic systems: O-NHC coupling in M/NHC catalysis // Chem. Sci. 2018. V. 9. P. 5564. https://doi.org/10.1039/C8SC01353E
Gaussian 16, Revision C.01, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A.V., Bloino J., Janesko B.G., et al., Fox, D.J. Gaussian, Inc., Wallingford CT, 2016.
Adamo C., Barone V. Toward reliable density functional methods without adjustable parameters: The PBE0 model // J. Chem. Phys. 1999. V. 110. P. 6158. https://doi.org/10.1063/1.478522
Weigend F., Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy // Phys. Chem. Chem. Phys. 2005. V. 7. P. 3297. https://doi.org/10.1039/B508541A
Grimme S., Ehrlich S., Goerigk L. Effect of the damping function in dispersion corrected density functional theory // J. Comput. Chem. 2011. V. 32. P. 1456. https://doi.org/10.1002/jcc.21759
Scalmani G., Frisch M.J. Continuous surface charge polarizable continuum models of solvation. I. General formalism // J. Chem. Phys. 2010. V. 132. P. 114110. https://doi.org/10.1063/1.3359469