BSU bulletin. Chemistry. Physics
Bibliographic description:
, , , , OPERANDO STUDY OF THE COUPLING REACTIONS USING LIGAND-FREE PALLADIUM CATALYSTS // BSU bulletin. Chemistry. Physics. - 2016. №4. . - С. 26-36.
Title:
OPERANDO STUDY OF THE COUPLING REACTIONS USING LIGAND-FREE PALLADIUM CATALYSTS
Financing:
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Annotation:
The combined application of UV-spectroscopy and GC-MS has been used to control the amount of oxidized palladium in situ under the Heck reaction with benzoic anhydride as well as indole direct arylation using the catalytic systems based on PdX2 salt (II). It has been established that under the Heck reaction the majority of loaded Pd (up to 90%) are in [PdBr4]2- form possessing no catalytic activity. In the direct arylation of indole the amount of oxidized Pd in the inactive [PdI4]2- form does not exceed 25% of Pd loaded.
Keywords:
Heck reaction, direct arylation, catalysis, palladium, [PdBr4]2- form pos-
sessing no catalytic activity, operando-spectroscopy, UV-spectroscopy.
sessing no catalytic activity, operando-spectroscopy, UV-spectroscopy.
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cross-coupling: a historical contextual perspective to the 2010 Nobel Prize // Angew. Chem. Int. Ed. — 2012. — V. 51, № 21. — P. 5062—5085.
2. Stephan M. S., Teunissen A. J. J. M., Verzijl G. K. M., de Vries J. G. Heck reactions without salt formation: aromatic carboxylic anhydrides as arylating agents // Angew. Chem. — 1998. — V. 37, № 5.- P. 662-664.
3. Jutand A., Negri S., de Vries J. G. Rate and mechanism of the oxidative addition of benzoic anhydride to palladium(0) complexes in DMF // Eur. J. Inorg. Chem. — 2002.— V. 2002, № 7. — P. 1711-1717.
4. Шмидт А. Ф., Смирнов В. В. Исследование механизма реакции арилирования алкенов ангидридами ароматических кислот методом ЯМР // Кинетика и катализ. —2002. — Т. 43, № 2. — С. 215-218.
5. Cano R., Schmidt A. F., McGlacken G. P. Direct arylation and heterogeneous ca- talysis; ever the twain shall meet // Chem. Sci. — 2015. — V. 6. — P. 5338-5346.
6. Rossi R., Lessi M., Manzini C., Marianetti G., Bellina F. Direct (hetero)arylation reactions of (hetero)arenes as tools for the step- and atom-economical synthesis of biologi- cally active unnatural compounds including pharmaceutical targets // Synthesis. — 2016.— V. 48. — P. 3821-3862.
7. Huang Y., Lin Z., Cao R. Palladium nanoparticles encapsulated in a metal-organic framework as efficient heterogeneous catalyst for direct C-2 arylation of indoles // Chem. Eur. J. — 2011. — V. 17, № 45. — P. 12706-12712.
8. Wang L., Yi W., Cai C. Fluorous silica gel-supported perfluoro-tagged palladium nanoparticles: an efficient and reusable catalyst for direct C-2 arylation of indoles // Chem. Comm. — 2011. — № 47. — P. 806-808.
9. Reimann S., Stoetzel, J., Frahm R. and al. Identification of the active species gen- erated from supported Pd catalysts in Heck reactions: an in situ quick scanning EXAFS investigation // J. Am. Chem. Soc. — 2011. — V. 133, № 11. — P. 3921-3930.
10. Шмидт А. Ф., Маметова Л. В., Дмитриева Т. В., Шмидт Е. Ю., Ткач В. С. О состоянии палладия в процессе синтеза стирола по Хеку // Изв. АН СССР. Серия химич. — 1991. — № 1. — С. 208.
11. Шмидт А. Ф., Аль-Халайка А., Смирнов В. В., Курохтина А. А. О состоянии палладия в «безлигандных» каталитических системах для реакции Хека с неактивированным бромбензолом // Кинетика и катализ. — 2008. — Т. 49, № 5. — C. 669-674.
12. Шмидт А. Ф., Смирнов В. В. Применение ангидридов ароматических кислот в качестве арилирующих агентов в реакции Хека // Кинетика и катализ. — 2000. — Т. 41, № 6. — С. 820-822.
13. The Mizoroki-Heck reaction / Ed. by M. Oestreich. — Hoboken: A John Wiley and Sons, 2009. — 608 p.
14. Phan N. T. S., Van Der Sluys M., Jones C. W. On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings — homogeneous or heterogeneous catalysis, a critical review // Adv. Synth. Catal. — 2006. — V. 348, № 6. — P. 609-679.
15. Schmidt A. F., Al Halaiqa A., Smirnov V. V. Interplays between reactions within and without the catalytic cycle of the Heck reaction as a clue to the optimization of the syn- thetic protocol // Synlett. — 2006. — № 18. — P. 2861-2878.
16. de Vries J. G. A unifying mechanism for all high-temperature Heck reactions. The role of palladium colloids and anionic species // Dalton Trans. — 2006. — № 3. — P. 421-429.
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