Recent developments in C–C bond formation catalyzed by solid supported palladium: a greener perspective
-
Debasree Saha
Abstract
The world today is struggling to achieve sustainable means for synthetic processes. Standing at this juncture, we need to develop and implement greener and reusable approaches towards organic synthesis. Transition metals especially palladium is a wonder element which has the ability to catalyze a range of useful organic syntheses. However, the expensive nature of palladium has urged synthetic chemists to search for protocols where a single palladium source may be used repeatedly in successive reactions, thus making the overall process cost effective. Palladium when anchored to solid supports leads to catalytic systems which can be easily separated from the organic phase post reaction and can be reused in successive cycles. Not only does this make the process economically viable but also ensures that no metal contaminates the purity of the final organic product. In this review we will highlight the recent developments in C–C bond formation (which is by far the most fundamental mode of bond making in organic synthesis) via the use of solid supported palladium catalytic systems. We will use this opportunity to illustrate the synthetic processes from a greener sustainable point of view which we feel is of utmost relevance in the current scientific scenario.
-
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: None declared.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Bej, A, Ghosh, K, Sarkar, A, Knight, DW. Palladium nanoparticles in the catalysis of coupling reactions. RSC Adv 2016;6:11446–53, https://doi.org/10.1039/c5ra26304b.Suche in Google Scholar
2. Taladriz-Blanco, P, Hervés, P, Pérez-Juste, J. Supported Pd nanoparticles for carbon-carbon coupling reactions. Top Catal 2013;56:1154–70, https://doi.org/10.1007/s11244-013-0082-6.Suche in Google Scholar
3. García-Suárez, EJ, Lara, P, García, AB, Philippot, K. Carbon-supported palladium and ruthenium nanoparticles: application as catalysts in alcohol oxidation, cross-coupling and hydrogenation reactions. Recent Pat Nanotechnol 2013;7:247–64.10.2174/187221050703131127110716Suche in Google Scholar PubMed
4. Molnár, Á. Palladium-Catalyzed Coupling Reactions: Practical Aspects, Future Developments. Weinheim: Wiley VCH; 2013.10.1002/9783527648283Suche in Google Scholar
5. Jana, R, Pathak, TP, Sigman, MS. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem Rev 2011;111:1417–92, https://doi.org/10.1021/cr100327p.Suche in Google Scholar PubMed PubMed Central
6. Fihri, A, Bouhrara, M, Nekoueishahraki, B, Basset, J-M, Polshettiwar, V. Nanocatalysts for Suzuki cross-coupling reactions. Chem Soc Rev 2011;40:5181–203, https://doi.org/10.1039/c1cs15079k.Suche in Google Scholar PubMed
7. Lamblin, M, Nassar-Hardy, L, Hierso, JC, Fouquet, E, Felpin, FX. Recyclable heterogeneous palladium catalysts in pure water: sustainable developments in Suzuki, Heck, Sonogashira and Tsuji–Trost reactions. Adv Synth Catal 2010;352:33–79, https://doi.org/10.1002/adsc.200900765.Suche in Google Scholar
8. Zolfigol, MA, Khakyzadeh, V, Mossavi-Zare, AR, Rostami, A, Zare, A, Iranpoor, N, et al.. Green Chem 2013;15:2132–40. https://doi.org/10.1039/c3gc40421h.Suche in Google Scholar
9. Gholinejad, M, Naghshbandi, Z, Nájera, C. Carbon-derived supports for palladium nanoparticles as catalysts for carbon-carbon bonds formation. ChemCatChem 2019;11:1792–823, https://doi.org/10.1002/cctc.201802101.Suche in Google Scholar
10. Ghaderia, A, Gholinejad, M, Firouzabadi, H. Palladium deposited on naturally occurring supports as a powerful catalyst for carbon-carbon bond formation reactions. Curr Org Chem 2016;20:327–48.10.2174/1385272819666150423202719Suche in Google Scholar
11. Felpin, F-X, Ayad, T, Mitra, S. Pd/C: an old catalyst for new applications – its use for the Suzuki–Miyaura reaction. Eur J Org Chem 2006:2679–90, https://doi.org/10.1002/ejoc.200501004.Suche in Google Scholar
12. Maegawa, T, Kitamura, Y, Sako, S, Udzu, T, Sakurai, A, Tanaka, A, et al.. Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki–Miyaura coupling reactions in aqueous media. Chem Eur J 2007;13:5937–43, https://doi.org/10.1002/chem.200601795.Suche in Google Scholar PubMed
13. Duplais, C, Forman, AJ, Baker, BA, Lipshutz, BH. UC Pd: a new form of Pd/C for Sonogashira couplings. Chem Eur J 2010;16:3366–71, https://doi.org/10.1002/chem.200902471.Suche in Google Scholar PubMed PubMed Central
14. Tang, W, Li, J, Jin, X, Sun, J, Huang, J, Li, R. Magnetically recyclable Fe@Pd/C as a highly active catalyst for Suzuki coupling reaction in aqueous solution. Catal Commun 2014;43:75–8, https://doi.org/10.1016/j.catcom.2013.09.001.Suche in Google Scholar
15. Siamaki, AR, Lin, Y, Woodberry, K, Connell, JW, Gupton, BF. Palladium nanoparticles supported on carbon nanotubes from solventless preparations: versatile catalysts for ligand-free Suzuki cross coupling reactions. J Mater Chem 2013;1:12909–18, https://doi.org/10.1039/c3ta12512b.Suche in Google Scholar
16. Ghorbani-Vaghei, R, Hemmati, S, Hashemi, M, Veisi, H. Diethylenetriamine-functionalized single-walled carbon nanotubes (SWCNTs) to immobilization palladium as a novel recyclable heterogeneous nanocatalyst for the Suzuki–Miyaura coupling reaction in aqueous media. Compt Rendus Chem 2015;18:636–43, https://doi.org/10.1016/j.crci.2014.10.010.Suche in Google Scholar
17. Khalili, D, Banazadeh, AR, Etemadi-Davan, E. Palladium stabilized by amino-vinyl silica functionalized magnetic carbon nanotube: application in Suzuki–Miyaura and Heck–Mizoroki coupling reactions. Catal Lett 2017;147:2674–87, https://doi.org/10.1007/s10562-017-2150-1.Suche in Google Scholar
18. Qu, K, Wu, L, Ren, J, Qu, X. Natural DNA-modified graphene/Pd nanoparticles as highly active catalyst for formic acid electro-oxidation and for the Suzuki Reaction. Appl Mater Interfaces 2012;4:5001–9, https://doi.org/10.1021/am301376m.Suche in Google Scholar PubMed
19. Kwon, TH, Cho, KY, Baek, K -Y, Yoon, HY, Moon Kim, B. Recyclable palladium–graphene nanocomposite catalysts containing ionic polymers: efficient Suzuki coupling reactions. RSC Adv 2017;7:11684–90, https://doi.org/10.1039/c6ra26998b.Suche in Google Scholar
20. Huang, Y, Wei, Q, Wang, Y, Dai, L. Three-dimensional amine-terminated ionic liquid functionalized graphene/Pd composite aerogel as highly efficient and recyclable catalyst for the Suzuki cross-coupling reactions. Carbon 2018;136:150–9, https://doi.org/10.1016/j.carbon.2018.04.068.Suche in Google Scholar
21. Shariatipour, M, Salamatmanesh, A, Jadidinejad, Mand Heydari, A Imidazole-aryl coupling reaction via C–H bond activation catalyzed by palladium supported on modified magnetic reduced graphene oxide in alkaline deep eutectic solvent. Catal Commun 2020;135:105890, https://doi.org/10.1016/j.catcom.2019.105890.Suche in Google Scholar
22. Nadagouda, MN, Polshettiwar, V, Varma, RS. Self-assembly of palladium nanoparticles: synthesis of nanobelts, nanoplates and nanotrees using vitamin B1, and their application in carbon–carbon coupling reactions. J Mater Chem 2009;19:2026–31, https://doi.org/10.1039/b817112b.Suche in Google Scholar
23. Leonhardt, SES, Stolle, A, Ondruschka, B, Cravotto, G, Leo, CD, Jandt, KD, et al.. Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis. Appl Catal Gen 2010;379:30–7, https://doi.org/10.1016/j.apcata.2010.02.029.Suche in Google Scholar
24. Firouzabadi, H, Iranpoor, N, Ghaderi, A. Gelatin as a bioorganic reductant, ligand and support for palladium nanoparticles. Application as a catalyst for ligand- and amine-free Sonogashira–Hagihara reaction. Org Biomol Chem 2011;9:865–71, https://doi.org/10.1039/c0ob00253d.Suche in Google Scholar PubMed
25. Firouzabadi, H, Iranpoor, N, Gholinejad, M, Kazemi, F. Agarose hydrogel as an effective bioorganic ligand and support for the stabilization of palladium nanoparticles. Application as a recyclable catalyst for Suzuki–Miyaura reaction in aqueous media. RSC Adv 2011;1:1013–9, https://doi.org/10.1039/c1ra00480h.Suche in Google Scholar
26. Cacchi, S, Caponetti, E, Casadei, MA, Giulio, AD, Fabrizi, G, Forte, G, et al.. Suzuki-Miyaura cross-coupling of arenediazonium salts catalyzed by alginate/gellan-stabilized palladium nanoparticles under aerobic conditions in water. Green Chem. 2012;14:317–20, https://doi.org/10.1039/c2gc15679b.Suche in Google Scholar
27. Kalbasi, RJ, Mosaddegh, N, Abbaspourrad, A Palladium nanoparticles supported on a poly(N-vinyl-2-pyrrolidone)-modified mesoporous carbon nanocage as a novel heterogeneous catalyst for the Heck reaction in water. Tetrahedron Lett 2012;53:3763–6.10.1016/j.tetlet.2012.05.046Suche in Google Scholar
28. Baloutaki, BA, Sayahi, MH, Nikpassand, M, Kefayati, H. Palladium supported terpyridine modified magnetic nanoparticles as an efficient catalyst for carbon–carbon bond formation. J Organomet Chem 2021;935:121682–8, https://doi.org/10.1016/j.jorganchem.2021.121682.Suche in Google Scholar
© 2022 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Reviews
- Recent endeavors in microbial remediation of micro- and nanoplastics
- Metal nanoparticles and its application on phenolic and heavy metal pollutants
- The story of nitrogen
- Recent development of imidazole derivatives as potential anticancer agents
- Indole based prostate cancer agents
- Lawsone (2-hydroxy-1,4-naphthaquinone) derived anticancer agents
- Small modular nuclear reactors are mostly bad policy
- A holistic environmental investigation of complementary energy in Alberta
- Green synthesis of various saturated S-heterocyclic scaffolds: an update
- Recent advances of heterocycle based anticancer hybrids
- Molecular docking and MD: mimicking the real biological process
- Synthesis of quinazolinone and quinazoline derivatives using green chemistry approach
- Nuclear fusion: the promise of endless energy
- Finance for Green Chemistry through Currency Mix
- Synthesis of bioactive scaffolds catalyzed by agro-waste-based solvent medium
- Recent developments in the green synthesis of biologically relevant cinnolines and phthalazines
- Detection of Rapid Eye Movement Behaviour Sleep Disorder using Time and Frequency Analysis of EEG Signal Applied on C4-A1 Channels
- Recent developments in C–C bond formation catalyzed by solid supported palladium: a greener perspective
- Visible-light-mediated metal-free C–Si bond formation reactions
- An overview of quinoxaline synthesis by green methods: recent reports
- Naturally occurring, natural product inspired and synthetic heterocyclic anti-cancer drugs
- Synthesis of bioactive natural products and their analogs at room temperature – an update
- One-pot multi-component synthesis of diverse bioactive heterocyclic scaffolds involving 6-aminouracil or its N-methyl derivatives as a versatile reagent
- Synthesis of new horizons in benzothiazole scaffold and used in anticancer drug development
- Triazine based chemical entities for anticancer activity
- Modification of kaolinite/muscovite clay for the removal of Pb(II) ions from aqueous media
- In silico design of ACE2 mutants for competitive binding of SARS-CoV-2 receptor binding domain with hACE2
- Computational study of Cu n AgAu (n = 1–4) clusters invoking DFT based descriptors
- Development of an online assessment system to evaluate knowledge on chemical safety and security
- Developing a questionnaire for diabetes mellitus type 2 risk effects and precondition factors – multivariate statistical paths
- Antioxidant and antibacterial activities of two xanthones derivatives isolated from the leaves extract of Anthocleista schweinfurthii Gilg (Loganiaceae)
- The stability increase of α-amylase enzyme from Aspergillus fumigatus using dimethyladipimidate
- Sustainability of ameliorative potentials of urea spiked poultry manure biochar types in simulated sodic soils
- Cytotoxicity test and antibacterial assay on the compound produced by the isolation and modification of artonin E from Artocarpus kemando Miq.
- Effects of alum, soda ash, and carbon dioxide on 40–50 year old concrete wastewater tanks
Artikel in diesem Heft
- Frontmatter
- Reviews
- Recent endeavors in microbial remediation of micro- and nanoplastics
- Metal nanoparticles and its application on phenolic and heavy metal pollutants
- The story of nitrogen
- Recent development of imidazole derivatives as potential anticancer agents
- Indole based prostate cancer agents
- Lawsone (2-hydroxy-1,4-naphthaquinone) derived anticancer agents
- Small modular nuclear reactors are mostly bad policy
- A holistic environmental investigation of complementary energy in Alberta
- Green synthesis of various saturated S-heterocyclic scaffolds: an update
- Recent advances of heterocycle based anticancer hybrids
- Molecular docking and MD: mimicking the real biological process
- Synthesis of quinazolinone and quinazoline derivatives using green chemistry approach
- Nuclear fusion: the promise of endless energy
- Finance for Green Chemistry through Currency Mix
- Synthesis of bioactive scaffolds catalyzed by agro-waste-based solvent medium
- Recent developments in the green synthesis of biologically relevant cinnolines and phthalazines
- Detection of Rapid Eye Movement Behaviour Sleep Disorder using Time and Frequency Analysis of EEG Signal Applied on C4-A1 Channels
- Recent developments in C–C bond formation catalyzed by solid supported palladium: a greener perspective
- Visible-light-mediated metal-free C–Si bond formation reactions
- An overview of quinoxaline synthesis by green methods: recent reports
- Naturally occurring, natural product inspired and synthetic heterocyclic anti-cancer drugs
- Synthesis of bioactive natural products and their analogs at room temperature – an update
- One-pot multi-component synthesis of diverse bioactive heterocyclic scaffolds involving 6-aminouracil or its N-methyl derivatives as a versatile reagent
- Synthesis of new horizons in benzothiazole scaffold and used in anticancer drug development
- Triazine based chemical entities for anticancer activity
- Modification of kaolinite/muscovite clay for the removal of Pb(II) ions from aqueous media
- In silico design of ACE2 mutants for competitive binding of SARS-CoV-2 receptor binding domain with hACE2
- Computational study of Cu n AgAu (n = 1–4) clusters invoking DFT based descriptors
- Development of an online assessment system to evaluate knowledge on chemical safety and security
- Developing a questionnaire for diabetes mellitus type 2 risk effects and precondition factors – multivariate statistical paths
- Antioxidant and antibacterial activities of two xanthones derivatives isolated from the leaves extract of Anthocleista schweinfurthii Gilg (Loganiaceae)
- The stability increase of α-amylase enzyme from Aspergillus fumigatus using dimethyladipimidate
- Sustainability of ameliorative potentials of urea spiked poultry manure biochar types in simulated sodic soils
- Cytotoxicity test and antibacterial assay on the compound produced by the isolation and modification of artonin E from Artocarpus kemando Miq.
- Effects of alum, soda ash, and carbon dioxide on 40–50 year old concrete wastewater tanks
