Abstract
Complexes of palladium(II) with N-heterocyclic carbenes of the PEPPSI-type were synthesized by the reaction of PdCl2 with 1-adamantyl-3-(R-methyl)-1H-imidazolium salts. These complexes were used as productive precatalysts for substituted thiophene and imidazole arylation by C—H-activation.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
N-Heterocyclic Carbenes. Effective Tools for Organometallic Synthesis, Ed. S. P. Nolan, Wiley-VCH, Weinheim, 2014, 568 pp.
W. A. Herrmann, Angew. Chem., Int. Ed., 2002, 41, 1290.
F. E. Hahn, M. C. Jahnke, Angew. Chem., Int. Ed., 2008, 47, 3122.
M. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature, 2014, 510, 485.
A. Yu. Chernenko, D. V. Pasyukov, A. V. Astakhov, V. A. Tafeenko, V. M. Chernyshev, Russ. Chem. Bull., 2018, 67, 1196.
C. J. O’Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J., 2006, 12, 4743.
E. A. B. Kantchev, C. J. O’Brien, M. G. Organ, Angew. Chem., Int. Ed., 2007, 46, 2768.
C. Valente, S. Çalimsiz, K. H. Hoi, D. Mallik, M. Sayah, M. G. Organ, Angew. Chem., Int. Ed., 2012, 51, 3314.
C. Valente, M. Pompeo, M. Sayah, M. G. Organ, Org. Process Res. Dev., 2014, 18, 180.
H. Baier, A. Kelling, H.-J. Holdt, Eur. J. Inorg. Chem., 2015, 2015, 1950.
D.-D. Lu, X.-X. He, F.-S. Liu, J. Org. Chem., 2017, 82, 10898.
A. Yu. Chernenko, A. V. Astakhov, D. V. Pasyukov, P. V. Dorovatovskii, Ya. V. Zubavichus, V. N. Khrustalev, V. M. Chernyshev, Russ. Chem. Bull., 2018, 67, 79.
B. Atwater, N. Chandrasoma, D. Mitchell, M. J. Rodriguez, M. Pompeo, R. D. J. Froese, M. G. Organ, Angew. Chem., Int. Ed., 2015, 54, 9502.
B. Atwater, N. Chandrasoma, D. Mitchell, M. J. Rodriguez, M. G. Organ, Chem. Eur. J., 2016, 22, 14531.
G. Dahm, C. Bailly, L. Karmazin, S. Bellemin-Laponnaz, J. Organometal. Chem., 2015, 794, 115–124.
S. Shi, M. Szostak, Chem. Commun., 2017, 53, 10584.
F.-D. Huang, C. Xu, D.-D. Lu, D.-S. Shen, T. Li, F.-S. Liu, J. Org. Chem., 2018, 83, 9144.
M. Sayah, A. J. Lough, M. G. Organ, Chem. Eur. J., 2013, 19, 2749.
M. A. Shevchenko, Y. N. Tkachenko, A. V. Astakhov, O. V. Khazipov, R. V. Tyurin, D. V. Pasyukov, V. A. Tafeenko, O. A. Kravchenko, V. M. Chernyshev, Russ. Chem. Bull., 2018, 67, 1684.
J. D. Dooley, S. R. Chidipudi, H. W. Lam, J. Am. Chem. Soc., 2013, 135, 10829.
J. Luo, S. Preciado, I. Larrosa, J. Am. Chem. Soc., 2014, 136, 4109.
J. A. Lee, C.K. Luscombe, ACS Macro Lett., 2018, 7, 767.
V. A. Glushkov, M. S. Denisov, A. A. Gorbunov, Yu. A. Myalitzin, M. V. Dmitriev, P. A. Slepukhin, Chem. Heterocycl. Compd., 2019, 55, 217.
N. Kaloğlu, M. Kaloğlu, M.N. Tahir, C. Arici, C. Bruneau, H. Doucet, P. H. Dixneuf, B. Çetinkaya, İ. Özdemir, J. Organometal. Chem., 2018, 867, 404.
X.-B. Shen, Y. Zhang, W.-X. Chen, Z.-K. Xiao, T.-T. Hu, L.-X. Shao, Org. Lett., 2014, 16, 1984.
X.-X. He, Y. Li, B.-Bei Ma, Z. Ke, F.-S. Liu, Organometallics, 2016, 35, 2655.
H.-H. Li, R. Maitra, Y.-T. Kuo, J.-H. Chen, C.-H. Hu, H. M. Lee, Appl. Organomet. Chem., 2017, 32, 3956.
L.-Q. Hu, R.-L. Deng, Y.-F. Li, C.-J. Zeng, D.-S. Shen, F.-Shou Liu, Organometallics, 2018, 37, 214.
Y.-Y. Lee, H.-W. Zseng, Z.-H. Tsai, Y.-S. Su, C.-H. Hu, H. M. Lee, Organometallics, 2019, 38, 805.
R. Maity, A. Verma, M. van der Meer, S. Hohloch, B. Sarkar, Eur. J. Inorg. Chem., 2016, 2016, 111.
M. G. Organ, S. Avola, I. Dobovyk, N. Hadei, E. A. B. Kantchev, C. J. O’Brien, Chem. Eur. J., 2006, 12, 4749.
M. E. H. Mazumder, P. Beale, C. Chan, J. Q. Yu, F. Huq, ChemMedChem, 2012, 7, 1840.
M. Mondal, J. Choudhury, J. Mol. Catal. A: Chemical, 2017, 426, 451.
V. A. Likholobov, N. K. Eremenko, V. N. Zudin, Izv. SO AN SSSR. Ser. Khim. Nauk [Bulletin of Siberian Branch of Academy of Sciences of USSR, Chem. Div.], 1976, 102 (in Russian).
R. Bhaskar, A. K. Sharma, A. K. Singh, Organometallics, 2018, 37, 2669.
P. V. Kumar, W.-Shien Lin, J.-S. Shen, D. Nandi, H. M. Lee, Organometallics, 2011, 30, 5160.
F. Churruca, S. Hernández, M. Perea, R. SanMartin, E. Domínguez, Chem. Commun., 2013, 49, 1413.
D. B. Eremin, V. P. Ananikov, Coord. Chem. Rev., 2017, 346, 2.
A. V. Rassolov, G. N. Baeva, I. S. Mashkovsky, A. Yu. Stakheev, Mendeleev Commun., 2018, 28, 538.
Y.-Y. An, J.-G. Yu, Y.-F. Han, Chin. J. Chem., 2019, 37, 76.
G. F. Raenko, N. I. Korotkikh, T. M. Pekhtereva, O. P. Shvaika, Russ. J. Org. Chem., 2001, 37, 1153.
U. M. Dzhemilev, N. R. Popodko, E. V. Kozlova, in Metallokompleksnyi kataliz v organicheskom sinteze [Metal Complex Catalysis in Organic Synthesis], Ed. U. M. Dzhemilev, Khimiya, Moscow, 1999, p. 109 (in Russian).
M. Pazicky, A. Loos, M. J. Ferreira, D. Serra, N. Vinokurov, F. Rominger, C. Jakel, A. S. K. Hashmi, M. Limbach, Organometallics, 2010, 29, 4448.
M. G. Voronkov, V. Udre, A. O. Taube, Khim. Geterotsikl. Soed., 1971, 6, 755 [Chem. Heterocycl. Compd. (Engl. Transl.), 1971, 6].
J. Roger, H. Doucet, Tetrahedron, 2009, 65, 9772.
G. M. Sheldrick, Acta Crystallogr., 2008, A64, 112.
G. M. Sheldrick, Acta Crystallogr., 2015, C71, 3.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystdllogr., 2009, 42, 339.
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the V International Scientific Conference “Advances in Synthesis and Complexing” (April 22–26, 2019, Moscow, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2039–2047, November, 2019.
The work was financially supported by the Russian Foundation for Basic Research (Project No. 17-03-00456-a).
Rights and permissions
About this article
Cite this article
Denisov, M.S., Dmitriev, M.V., Gorbunov, A.A. et al. Complexes of palladium(II) with N-heterocyclic carbenes from adamantylimidazole as precatalysts for thiophene and imidazole arylation. Russ Chem Bull 68, 2039–2047 (2019). https://doi.org/10.1007/s11172-019-2664-3
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-019-2664-3