Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives

Fatma Belkessam, Aidene Mohand, Jean-François Soulé, Abdelhamid Elias and Henri Doucet
Beilstein J. Org. Chem. 2014, 10, 2912–2919. https://doi.org/10.3762/bjoc.10.309

Supporting Information

Supporting Information File 1: Experimental procedures and characterization data.
Format: PDF Size: 345.8 KB Download

Cite the Following Article

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives
Fatma Belkessam, Aidene Mohand, Jean-François Soulé, Abdelhamid Elias and Henri Doucet
Beilstein J. Org. Chem. 2014, 10, 2912–2919. https://doi.org/10.3762/bjoc.10.309

How to Cite

Belkessam, F.; Mohand, A.; Soulé, J.-F.; Elias, A.; Doucet, H. Beilstein J. Org. Chem. 2014, 10, 2912–2919. doi:10.3762/bjoc.10.309

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

  • Nguyen, H.; Luong, T. T.; Nguyen, N. B.; Le, H. T.; Chi P, M.; Meervelt, L. V.; Do, M. T.; Dang, T. T. Synthesis of mono- and tetra-arylated tetrathienylethene via direct palladium-catalyzed C–H arylation: A useful method for tuning luminescent properties of arylated tetrathienylethenes. Tetrahedron 2023, 142, 133539. doi:10.1016/j.tet.2023.133539
  • Vallan, L.; Istif, E.; Gómez, I. J.; Alegret, N.; Mantione, D. Thiophene-Based Trimers and Their Bioapplications: An Overview. Polymers 2021, 13, 1977. doi:10.3390/polym13121977
  • Le, T. T.; Phan, S. T.; Le, H. T. H.; Nguyen, H. T.; Dang, T. T.; Le, T. T. Palladium-Catalyzed Direct Mono- and Diarylation of Diphenydithienylethenes: A Useful Method for Enhancing Fluorescence Intensity and Aggregation-Induced Emission. Molbank 2021, 2021, M1210. doi:10.3390/m1210
  • Messina, C.; Douglas, L. Z.; Liu, J. T.; Forgione, P. Successive Pd‐Catalyzed Decarboxylative Cross‐Couplings for the Modular Synthesis of Non‐Symmetric Di‐Aryl‐Substituted Thiophenes. European Journal of Organic Chemistry 2020, 2020, 5182–5191. doi:10.1002/ejoc.202000780
  • Ismail, M. A.; El-Sayed, W. M.; Shaaban, S.; Abdelwahab, G. A.; Hamama, W. S. A Review of Cationic Arylfurans and Their Isosteres: Synthesis and Biological Importance. Current Organic Chemistry 2020, 23, 2751–2782. doi:10.2174/1385272823666191029114830
  • Rizwan, K.; Zubair, M.; Rasool, N.; Mahmood, T.; Ayub, K.; Alitheen, N. B.; Aziz, M. N. M.; Akhtar, M. N.; Nasim, F.-u.-H.; Bukhary, S. M.; Ahmad, V. U.; Rani, M. Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations. Chemistry Central journal 2018, 12, 49. doi:10.1186/s13065-018-0404-7
  • Sadowski, B.; Rode, M. F.; Gryko, D. T. Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red-Emitting Dyes with Conformational Freedom. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 24, 855–864. doi:10.1002/chem.201702306
  • Marzo, L.; Ghosh, I.; Esteban, F. J. P.; König, B. Metal-Free Photocatalyzed Cross Coupling of Bromoheteroarenes with Pyrroles. ACS Catalysis 2016, 6, 6780–6784. doi:10.1021/acscatal.6b01452
  • Morimoto, K.; Nakamura, A.; Dohi, T.; Kita, Y. Metal‐Free Oxidative Cross‐Coupling Reaction of Thiophene Iodonium Salts with Pyrroles. European Journal of Organic Chemistry 2016, 2016, 4294–4297. doi:10.1002/ejoc.201600791
  • Castro, M. C. R.; Raposo, M. M. M. Synthesis of π-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions. Tetrahedron 2016, 72, 1881–1887. doi:10.1016/j.tet.2016.02.054
  • He, X.-X.; Li, Y.-F.; Huang, J.; Shen, D.-S.; Liu, F.-S. A convenient phosphine-free palladium-catalyzed direct arylation of thiazole under mild aerobic conditions. Journal of Organometallic Chemistry 2016, 803, 58–66. doi:10.1016/j.jorganchem.2015.12.009
  • Idris, I.; Derridj, F.; Djebbar, S.; Soulé, J.-F.; Doucet, H. Synthesis of symmetrical and unsymmetrical 1,3-diheteroarylbenzenes through palladium-catalyzed direct arylation of benzene-1,3-disulfonyl dichloride and 3-bromobenzenesulfonyl chlorides. Tetrahedron 2015, 71, 9617–9625. doi:10.1016/j.tet.2015.10.082
  • Saoudi, B.; Debache, A.; Soulé, J.-F.; Doucet, H. Synthesis of heteroarenes dyads from heteroarenes and heteroarylsulfonyl chlorides via Pd-catalyzed desulfitative C–H bond heteroarylations. RSC Advances 2015, 5, 65175–65183. doi:10.1039/c5ra07762a
Other Beilstein-Institut Open Science Activities