Volume 8, Issue 2, June 2020, Page: 18-22
Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts
Abdol Reza Hajipour, Department of Chemistry, Isfahan University of Technology, Isfahan, Iran; Department of Neuroscience, University of Wisconsin, Madison, USA
Zahra Khorsandi, Department of Chemistry, Isfahan University of Technology, Isfahan, Iran
Received: Apr. 20, 2020;       Accepted: May 5, 2020;       Published: Jun. 28, 2020
DOI: 10.11648/j.mc.20200802.11      View  6      Downloads  3
Extensive studies of asymmetric intermolecular Heck reaction are described and provide a deeper insight into histidine-catalyzed. In particular, aspects of enantio- as well as diastereoselectivity of these reactions are discussed. As the first report, we synthesized five histidine-based organocatalyts including histidine as a well-defined and biodegradable natural structure alone and in combination with 2,4,6-trichloro-1,3,5-triazine, benzene-1,3-diamine, dimethyl malonate and dimeric structure applied in the asymmetric intermolecular Heck reaction of aryl halides; their efficiency was compared to each other’s. These phosphine-free palladium catalysts were found as efficient catalytic system which provided the superior efficiency with excellent yields, regioselectivity and enantioselectivity. In these among, histidine with 2,4,6-trichloro-1,3,5-triazine which generate the star like molecule palladium catalyst gave the best activity in asymmetric intermolecular Heck reaction with excellent yields and good regio- and enantioselectivity under mild reaction conditions. The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates or aryl iodide in the rare reports of available Pd catalysts. Herein, we extend the reaction to aryl bromides. In addition, the scope of reaction was examined in two different techniques: conventional heating and microwave irradiation and compared. For the first time, microwave irradiation sintering is successfully used for this reaction. Comparison of catalytic activities of our catalyst (Pd/His) with literature examples confirmed our success.
Heck, Asymmetric Reaction, Palladium, Organocatalytst, Histidine
To cite this article
Abdol Reza Hajipour, Zahra Khorsandi, Asymmetric Intermolecular Heck Reaction of Aryl Halides by Pd-histidine Organocatalysts, Modern Chemistry. Vol. 8, No. 2, 2020, pp. 18-22. doi: 10.11648/j.mc.20200802.11
Copyright © 2020 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Ekpemo, S. C. (2018). Challenges and Outcome of Neonatal Surgery at the Abia State University Teaching Hospital Aba Nigeria. American Journal of Biomedical and Life Sciences, 6 (4), 69. doi: 10.11648/j.ajbls.20180604.11
Hyder, Z.; Ruan, J. X. (2008). Hydrogen-Bond-Directed Catalysis: Faster, Regioselective and Cleaner Heck Arylation of Electron-Rich Olefins in Alcohols. Chemistry: A European Journal, 14 (18), 5555. https://doi.org/10.1002/chem.200800411.
Yang, Z.; Zhou, J. (2012). Palladium-Catalyzed, Asymmetric Mizoroki–Heck Reaction of Benzylic Electrophiles Using Phosphoramidites as Chiral Ligands. Journal of the American Chemical Society, 134 (29), 11833. doi.org/10.1021/ja304099j.
Wu, C.; Zhou, J. (2014) Asymmetric Intermolecular Heck Reaction of Aryl Halides Journal of the American Chemical Society, 136 (2), 650-652. doi.org/10.1021/ja412277z
Lauer, M. G.; Thompson, M. K.; Shaughnessy, K. H. (2014) Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands. The Journal of Organic Chemistry, 79 (22), 10837-10848. doi.org/10.1021/jo501840u.
Beletskaya, P.; Cheprakov, A. V. (2000) The Heck Reaction as a Sharpening Stone of Palladium Catalysis. Chemical review, 100 (8), 3009. doi.org/10.1021/cr9903048.
Nicolaou, K. C.; Bulger, P. G; Sarlah D. (2005) Palladium-catalyzed cross-coupling reactions in total synthesis. Angewandte Chemie International Edition, 44 (29), 4442. DOI: 10.1002/anie.200500368
Magano J, Dunetz. J. (2011) Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals. Chemical Reviews, 111 (3), 2177.
Hajipour A R.; Khorsandi, Z.; Farrokhpour, H. (2016) Regioselective Heck reaction catalyzed by Pd nanoparticles immobilized on DNA-modified MWCNTs. RSC Advances, 6 (64), 59124.
Miller, S. J. (2004) In Search of Peptide-Based Catalysts for Asymmetric Organic Synthesis, Accounts of Chemical Research, 37 (8), 601. doi.org/10.1021/ar030061c
Yu, Z; Tantakitti Z, Palmer L, Stupp S. (2016) Asymmetric Peptide Nanoribbons, Nano Letters, 16 (11), 6967.
Li, S.; Mehta, A. K, Sidorov, A. N.; Orlando, T. M.; Jiang, Z.; Anthony, N. R.; Lynn, D. G. (2016) Design of Asymmetric Peptide Bilayer Membranes, Journal of the American Chemical Society, 138 (10), 3579.
Illa, O.; Porcar-Tost, O; Robledillo, C.; Elvira, C; Nolis, P.; Reiser, O.; Branchadell, V.; Ortuño, R. M. (2018) Stereoselectivity of Proline/Cyclobutane Amino Acid-Containing Peptide Organocatalysts for Asymmetric Aldol Additions: A Rationale. The Journal of Organic Chemistry, 83 (1), 350.
Avila-Ortiz, C. G., Díaz-Corona, L.; González, E. J; Juaristi, E. (2017) Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions, Molecules, 22, 1328. doi.org/10.3390/molecules22081328
Grünenfelder, C. E; Kisunzu, J. K.; Wennemers, H. (2016) Peptide-Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide. Angew Chem Int Ed Engl.,18, 8571. 10.1002/anie.201602230.
Sándor, B. Ö.; István, M. M.; Ferenc, F. (2012) Asymmetric aldol reaction in a continuous-flow reactor catalyzed by a highly reusable heterogeneous peptide. Journal of Catalysis. 295, 179. doi.org/10.1016/j.jcat.2012.08.006
Tsogoeva, S. B.; Shengwei, W. (2005) (S)-Histidine-based dipeptides as organic catalysts for direct asymmetric aldol reactions, Tetrahedron: Asymmetry, 16 (11), 1947. DOI: 10.1016/j.tetasy.2005.04.027
Soai, K.; Niwa, S.; Yamada, Y.; Inoue H. (1987) Chiral piperazine as a new chiral catalyst for the enantioselective addition of dialkyl zincs to aryl aldehydes, Tetrahedron Letter, 28 (41), 4841. doi.org/10.1016/S0040-4039(00)96639-5.
Kawasaki, T.; Omine, T.; Suzuki, K.; Sato, H.; Yamagishi, A.; Soai, K. (2009) Highly enantioselective asymmetric autocatalysis using chiral ruthenium complex-ion-exchanged synthetic hectorite as a chiral initiator, Organic Biomoleculat Chemistry, 7 (6), 1073. doi.org/10.1016/S0040-4039(00)96639-5.
Heck, R. F. (1979) Palladium-catalyzed reactions of organic halides with olefins, Accounts of Chemical Research, 12 (4), 146. doi.org/10.1021/ar50136a006
Nabid, M. R.; Bide, Y. (2014) H40-PCL-PEG unimolecular micelles both as anchoring sites for palladium nanoparticles and micellar catalyst for Heck reaction in water, Applied Catalysis A: General. 469, 183. doi.org/10.1016/j.apcata.2013.09.016.
Wang, Y.; Yang, Q.; Yang, L.; Shi, J.; Zhang, M. (2013) CuI/TBAB as a novel efficient catalytic system for Heck reaction in water, RSC Advances, 3 (44), 21251. doi.org/10.1039/C3RA44819C
Yang, F.; Fu, S. Y.; Chu, W.; Li, C.; Tong, D. G. (2014) Monodisperse amorphous CuB23 alloy short nanotubes: novel efficient catalysts for Heck coupling of inactivated alkyl halides and alkenes, RSC Advances, 4 (86), 45838. doi.org/10.1039/C4RA08517E
Jeffery, T.; David, M. (1998) [Pd/Base/QX] catalyst systems for directing Heck-type reactions, Tetrahedron Letters, 39 (32), 5751. doi.org/10.1016/S0040-4039(98)01135-6
Sabino, A. A.; Machado, A. H. L, Correia, C. R. D.; Eberlin, M. N. (2004) Probing the mechanism of the Heck reaction with arene diazonium salts by electrospray mass and tandem mass spectrometry. Angewandte Chemie Int. Ed., 43 (34), 2514. doi.org/10.1002/anie.200353076
Rosol, M.; Moyano, A. (2005) 1′-Carbopalladated-4-ferrocenyl-1,3-oxazolines as catalysts for Heck reactions: Further evidence in support of the Pd(0)/Pd(II) mechanism, Journal of Organometallic Chemistry, 690 (9), 2291. DOI: 10.1016/j.jorganchem.2005.02.035
Machado, A. H. L.; Sousa, M. A.; Patto, D. C.; Azevedo, S. L.; Bombonato, F. S. F.; Correia, C. R. D. (2009) The scope of the Heck arylation of enol ethers with arenediazonium salts: a new approach to the synthesis of flavonoids, Tetrahedron Letters, 50 (11), 1222. doi.org/10.1016/j.tetlet.2009.01.017.
Fontanilla, D.; Johannessen, M.; Hajipour, A. R.; Cozzi, N.; Jackson, V. M. B; Ruoho, A. E. (2009) The Hallucinogen N,N-Dimethyltryptamine (DMT) Is an Endogenous Sigma-1 Receptor Regulator, Science, 323 (5916), 934. doi: 10.1126/science.1166127.
Tu, T.; Deng, W.P.; Hou, X. L.; Dai, L. X.; Dong, X. C. (2003) The Regioselectivity of the Asymmetric Intermolecular Heck Reaction with Planar Chiral Diphosphine–Oxazoline Ferrocenyl Ligands, Chemistry—A European journal, 9 (13), 3073. doi.org/10.1002/chem.200204450.
Dai, W. M.; Yeung, K. K. Y.; Wang, Y. (2004) The first example of atropisomeric amide-derived P,O-ligands used for an asymmetric Heck reaction, Tetrahedron, 60 (20), 4425. DOI: 10.1016/j.tet.2004.02.062.
Rankic, D. A.; Lucciola, D.; Keay, B. A. (2010) Application of 3,3′-disubstituted xylBINAP derivatives in inter- and intramolecular asymmetric Heck/Mizoroki reactions, Tetrahedron Letters, 51 (43) 5724. DOI: 10.1016/j.tetlet.2010.08.078.
Hou, X. L.; Dong, D. X.; Yuan, K. (2004) Synthesis of new chiral benzylically substituted P,N-ligands and their applications in the asymmetric Heck reaction, Tetrahedron: Asymmetry, 15 (14), 2189. DOI: 10.1016/j.tetasy.2004.05.030.
Roszak, R.; Trzeciak, A. M.; Pernak, J.; Borucka, N. (2011) Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran, Applied Catalysis A: General, 409, 148. doi.org/10.1016/j.apcata.2011.09.038.
Hajipour, A. R.; Rezaei, F.; Khorsandi, Z. (2017) Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst, green chemistry, 19 (5), 1353. doi.org/10.1039/C6GC03377F.
Hajipour, A. R.; Khorsandi, Z. (2016) Immobilized Pd on (S)-methyl histidinate-modified multi-walled carbon nanotubes: a powerful and recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura C–C cross-coupling reactions in green solvents and under mild conditions, Applied Organometallic Chemistry, 30 (5), 256. doi.org/10.1002/aoc.3425.
Hajipour, A. R, Tadayoni, N. S.; Khorsandi, Z. (2016) Magnetic iron oxide nanoparticles–N-heterocyclic carbene–palladium (II): a new, efficient and robust recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions, Applied Organometallic Chemistry, 30 (7), 590. doi.org/10.1002/aoc.3475.
Hajipour, A. R.; Khorsandi, Z. (2016) A comparative study of the catalytic activity of Co- and CoFe2O4-NPs in C–N and C–O bond formation: synthesis of benzimidazoles and benzoxazoles from o-haloanilides, New Journal of Chemistry, 40 (12), 10474. doi.org/10.1039/C6NJ02293F.
Browse journals by subject