A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions

Year 2021, Volume: 17 Issue: 4, 405 - 415, 29.12.2021

Deniz Demir Atlı

Abstract

1-(2,5-dimethylbenzyl)benzimidazole (1) and 1,3-bis(2,5-dimethylbenzyl)benzimidazolium chloride (2) were prepared. The reaction of 2 with Pd(OAc)2, LiCl and Et3N gave [PdCl2{1,3-bis(2,5-dimethylbenzyl)benzimidazolin-2-ylidene}(PPh3)] (3) complex. The prepared compounds were characterized by NMR, FT-IR, elemental analysis and also LC-MSMS (for 3). The palladium complex 3 was used as catalyst in Suzuki –Miyaura cross-coupling reactions of some aryl bromides and chlorides with phenylboronic acid.

Keywords

Benzimidazolium, N-heterocyclic carbene, palladium, Suzuki-Miyaura cross-coupling

References

• 1. Miyaura, N, Yamada, K, Suzuki, A. 1979. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Letters; 20(36): 3437-3440.
• 2. Miyaura, N, Suzuki, A. 1979. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. Journal of the Chemical Society, Chemical Communications; 19: 866-867.
• 3. Pagett, AB, Lloyd-Jones, GC. Suzuki–Miyaura cross-coupling. In: Denmark SE et al. (ed.) Organic Reactions, Wiley, UK, 2019, pp 547-620.
• 4. Talukder, MM, Cue, JMO, Miller, JT, Gamage, PL, Aslam, A, McCandless, GT, Biewer, MC, Stefan, MC. 2020. Ligand steric effects of α-diimine nickel(II) and palladium(II) complexes in the Suzuki–Miyaura cross-coupling reaction. ACS Omega; 5(37): 24018-24032.
• 5. D’Accriscio, F, Ohleier, A, Nicolas, E, Demange, M, Boullay, OTD, Saffon-Merceron, N, Fustier-Boutignon, M, Rezabal, E, Frison, G, Nebra, N, Mezailles, N. 2020. [(dcpp)Ni(η2-Arene)] precursors: Synthesis, reactivity, and catalytic application to the Suzuki–Miyaura reaction. Organometallics; 39(10): 1688-1699.
• 6. Ansari, RM, Kumar, LM, Bhat, BR. 2018. Air-stable cobalt(II) and nickel(II) Complexes with schiff base Ligand for catalyzing Suzuki–Miyaura cross-coupling reaction. Russian Journal of Coordination Chemistry; 44: 1-8.
• 7. Key, RJ, Tengco, JMM, Smith, MD, Vannucci, AK. 2019. A molecular/heterogeneous nickel catalyst for Suzuki–Miyaura coupling. Organometallics; 38(9): 2007-2014.
• 8. Ansari, RM, Bhat, BR. 2017. Schiff base transition metal complexes for Suzuki–Miyaura cross-coupling reaction. Journal of Chemical Sciences; 129: 1483-1490.
• 9. Kadu, BS. 2021. Suzuki–Miyaura cross coupling reaction: recent advancements in catalysis and organic synthesis. Catalysis Science&Technology; 11(4): 1186-1221.
• 10. Pirkl, N, Grosso, AD, Mallick, B, Doppiuc, A, Gooben LJ. 2019. Dihalogen-bridged NHC–palladium(i) dimers: synthesis, characterisation and applications in cross-coupling reactions. Chemical Communications; 55(36): 5275-5278.
• 11. Kaloğlu, N, Özdemir, İ. 2019. PEPPSI-Pd-NHC catalyzed Suzuki-Miyaura cross-coupling reactions in aqueous media. Tetrahedron; 75(15): 2306-2313.
• 12. Sharma, KN, Satrawala, N, Srivastava, AK, Ali, M, Joshi, RK. 2019. Palladium(II) ligated with selenated NHC based (Se, CNHC, N−) type pincer: An efficient catalyst for Mizoroki-Heck and Suzuki Miyaura coupling in water. Organic&Biomolecular Chemistry; 17(40): 8969-8976.
• 13. Vaishya, V, Patider, S, Plania, M. 2021. Imidazolium/triazolium based NHC–Palladium complexes and their application in catalysis. Materials Today: Proceedings; 43: 3181-3187.
• 14. Schmid, TE, Jones, DC, Songis, O, Furst, MRL, Slawin, AMZ, Cazin, CSJ. 2013. Mixed phosphine/N-heterocyclic carbene palladium complexes: synthesis, characterization and catalytic use in aqueous Suzuki–Miyaura reactions. Dalton Transactions; 42(20): 7345-7353.
• 15. Aktaş, A, Erdemir, F, Celepci, DB, Gök, Y, Aygün, M. 2019. Mixed phosphine/N‑heterocyclic carbene–palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media. Transition Metal Chemistry; 44: 229-236.
• 16. Chan, KT, Tsai, YH, Lin, WS, Wu, JR, Chen, SJ, Liao, FX, Hu, CH, Lee, HM. 2010. Palladium complexes with carbene and phosphine ligands: Synthesis, structural characterization, and direct arylation reactions between aryl halides and alkynes. Organometallics; 29: 463-472.
• 17. Zhang, J, Zhang, W, wang, Y, Zhang, M. 2008. Palladium-iminodiacetic acid immobilized on pH-responsive polymeric microspheres: Efficient quasi-homogeneous catalyst for Suzuki and Heck reactions in aqueous solution. Advanced Synthesis & Catalysis; 350(13): 2065-2076.
• 18. Demir Atlı, D. 2020. Synthesis and catalytic application of cyclopentadienyl nickel(II) N-heterocyclic carbene complexes. Journal of Coordination Chemistry; 73(10): 1530-1537.
• 19. Achar, G, Agarwal, P, Brinda, KN, Malecki, JG, Keri, RS, Budagumpi, S. 2018. Ether and coumarin-functionalized (benz)imidazolium salts and their silver(I)-N-heterocyclic carbene complexes: Synthesis, characterization, crystal structures and antimicrobial studies. Journal of Organometallic Chemistry; 854: 64-75.
• 20. Kandil, S, Kariuki, BM, McGuian, C, Westwell, AD. 2021. Synthesis, biological evaluation and X-ray analysis of bicalutamide sulfoxide analogues for the potential treatment of prostate cancer. Bioorganic & Medicinal Chemistry Letters; 36: 127817.
• 21. Mansour, W, Suleiman, R, Fettouhi, M, Ali, BE. 2020. Soft heteroleptic N-heterocyclic carbene palladium(II) species for efficient catalytic routes to alkynones via carbonylative Sonogashira coupling. ACS Omega; 5(37): 23687-23702.
• 22. Zhou, YB, Li, CY, Lin, M, Ding, YJ, Zhan, ZP. 2015. A polymer-bound monodentate-P-ligated palladium complex as a recyclable catalyst for the Suzuki–Miyaura coupling reaction of aryl chlorides. Advanced Synthesis & Catalysis; 357(11): 2503-2508.
• 23. Shahnaz, N, Banik, B, Das, P. 2013. A highly efficient schiff-base derived palladium catalyst for the Suzuki–Miyaura reactions of aryl chlorides. Tetrahedron Letters; 54: 2886-2889.