N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides

Ismail Özdemir, Nevin Gürbüz, Nazan Kaloğlu, Öznur Doğan, Murat Kaloğlu, Christian Bruneau and Henri Doucet
Beilstein J. Org. Chem. 2013, 9, 303–312. https://doi.org/10.3762/bjoc.9.35

Cite the Following Article

N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides
Ismail Özdemir, Nevin Gürbüz, Nazan Kaloğlu, Öznur Doğan, Murat Kaloğlu, Christian Bruneau and Henri Doucet
Beilstein J. Org. Chem. 2013, 9, 303–312. https://doi.org/10.3762/bjoc.9.35

How to Cite

Özdemir, I.; Gürbüz, N.; Kaloğlu, N.; Doğan, Ö.; Kaloğlu, M.; Bruneau, C.; Doucet, H. Beilstein J. Org. Chem. 2013, 9, 303–312. doi:10.3762/bjoc.9.35

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Ulu, Ö. D.; Serin, S.; Özdemir, N.; Özdemir, İ. Synthesis, crystal structure, and DFT studies of NHC mediated Pd-PEPPSI complex: Application for Suzuki reaction. Journal of Molecular Structure 2024, 1320, 139479. doi:10.1016/j.molstruc.2024.139479
  • Şeker, S.; Doğan Ulu, Ö.; Gürbüz, N.; Özdemır, N.; Özdemır, İ.; Bülbül, H. Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct arylation of heteroaromatic species. Journal of Coordination Chemistry 2024, 77, 434–447. doi:10.1080/00958972.2024.2335629
  • Touj, N.; Bensalah, D.; Mansour, L.; Sauthier, M.; Gürbüz, N.; Özdemir, I.; Hamdi, N. Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct C H functionalization of five-membered heterocyclic bioactive motifs. Journal of Molecular Structure 2024, 1297, 136885. doi:10.1016/j.molstruc.2023.136885
  • Doğan Ulu, Ö.; Gürbüz, N.; Özdemir, İ. Pd-NHC Catalyzed C-H Functionalization. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier, 2024. doi:10.1016/b978-0-443-15742-4.00058-2
  • Bensalah, D.; Mansour, L.; Sauthier, M.; Gürbüz, N.; Özdemir, I.; Koko, W. S.; Gatri, R.; Hamdi, N. Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C–H arylation of heteroarenes with different aryl bromides and chlorides. New Journal of Chemistry 2023, 47, 20435–20455. doi:10.1039/d3nj04209j
  • Patel, R. K.; Chauhan, A.; Jha, P.; Kant, R.; Kumar, R. Catalytic Friedel-Crafts Alkylative Desymmetrization of Cyclohexa-2,5-dienones: Access to Linear and Bridged Polycyclic Pyrroles and 3-Arylpyrroles. Organic letters 2022, 24, 5422–5427. doi:10.1021/acs.orglett.2c02135
  • Horbaczewskyj, C. S.; Fairlamb, I. J. S. Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm. Organic process research & development 2022, 26, 2240–2269. doi:10.1021/acs.oprd.2c00051
  • Rossi, R.; Ciofalo, M. Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art. Current Organic Chemistry 2022, 26, 215–274. doi:10.2174/1385272826666220201124008
  • Kaloğlu, M.; Özdemir, N.; Özdemir, İ. 4,5‐Dihydro‐imidazol‐2‐ylidene‐linked palladium complexes as catalysts for the direct CH bond arylation of azoles. Applied Organometallic Chemistry 2022, 38. doi:10.1002/aoc.6551
  • Kaloğlu, M.; Slimani, I.; Özdemir, N.; Gürbüz, N.; Hamdi, N.; Özdemir, İ. The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts. Journal of Organometallic Chemistry 2021, 951, 122013. doi:10.1016/j.jorganchem.2021.122013
  • Hunjan, M. K.; Panday, S.; Gupta, A.; Bhaumik, J.; Das, P.; Laha, J. K. Recent Advances in Functionalization of Pyrroles and their Translational Potential. Chemical record (New York, N.Y.) 2021, 21, 715–780. doi:10.1002/tcr.202100010
  • Kaloğlu, M.; Kaloğlu, N.; Özdemir, İ. Palladium-PEPPSI-NHC Complexes Bearing Imidazolidin-2-Ylidene Ligand: Efficient Precatalysts for the Direct C5-Arylation of N-Methylpyrrole-2-Carboxaldehyde. Catalysis Letters 2021, 151, 1–16.
  • Kaloğlu, M.; Kaloğlu, N.; Özdemir, İ. Palladium-PEPPSI-NHC Complexes Bearing Imidazolidin-2-Ylidene Ligand: Efficient Precatalysts for the Direct C5-Arylation of N-Methylpyrrole-2-Carboxaldehyde. Catalysis Letters 2021, 151, 3197–3212. doi:10.1007/s10562-021-03561-4
  • Jalal, M.; Hammouti, B.; Touzani, R.; Aouniti, A.; Özdemir, İ. Metal-NHC heterocycle complexes in catalysis and biological applications: Systematic review. Materials today. Proceedings 2020, 31, S122–S129. doi:10.1016/j.matpr.2020.06.398
  • Ozdemir, I.; Ciftci, O.; Evren, E.; Gürbüz, N.; Kaloğlu, N.; Türkmen, N. B.; Yasar, S.; Üstün, E.; Hamdi, N.; Mansour, L.; Özdemir, İ. Synthesis, characterization and antitumor properties of novel silver(I) and gold(I) N-heterocyclic carbene complexes. Inorganica Chimica Acta 2020, 506, 119530. doi:10.1016/j.ica.2020.119530
  • Zhao, Q.; Meng, G.; Nolan, S. P.; Szostak, M. N-Heterocyclic Carbene Complexes in C–H Activation Reactions. Chemical reviews 2020, 120, 1981–2048. doi:10.1021/acs.chemrev.9b00634
  • Allenbaugh, R. J.; Zachary, J. R.; Underwood, A. N.; Bryson, J. D.; Williams, J. R.; Shaw, A. Kinetic analysis of the complete mechanochemical synthesis of a palladium(II) carbene complex. Inorganic Chemistry Communications 2020, 111, 107622. doi:10.1016/j.inoche.2019.107622
  • Yamaguchi, M.; Fujiwara, S.; Manabe, K. Synthesis of 2,2,5-Trisubstituted 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation. Organic letters 2019, 21, 6972–6977. doi:10.1021/acs.orglett.9b02559
  • Kaloğlu, M.; Kaloğlur, N.; Özdemir, İ. Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes. Chinese Journal of Chemistry 2018, 36, 837–844. doi:10.1002/cjoc.201800166
  • Kaloğlu, N.; Kaloğlu, M.; Tahir, M.; Arıcı, C.; Bruneau, C.; Doucet, H.; Dixneuf, P. H.; Çetinkaya, B.; Özdemir, İ. Synthesis of N -Heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation. Journal of Organometallic Chemistry 2018, 867, 404–412. doi:10.1016/j.jorganchem.2017.10.019
Other Beilstein-Institut Open Science Activities