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Mini-Reviews in Organic Chemistry

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ISSN (Online): 1875-6298

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Mini-Review Article

Palladium (Pd)-based Photocatalysts for Suzuki Coupling Reactions: An Overview

Author(s): Jeena Jyoti Boruah* and Siva Prasad Das*

Volume 20, Issue 7, 2023

Published on: 16 September, 2022

Page: [687 - 699] Pages: 13

DOI: 10.2174/1570193X19666220819093803

Price: $65

Abstract

Extensive research has been documented in the last few decades on the utilization of near IR, visible and UV light in organic chemical transformations. In this brief review, we provide an overview of the most noteworthy achievements in the area of photocatalytic Suzuki coupling reactions by palladium (Pd)-based catalytic systems. The works on different types of Pd-based photocatalysts for Suzuki coupling reaction and their characteristic as well as catalytic activity in terms of substrate scope, recyclability, TON or TOF are discussed herein.

Keywords: Suzuki-Miyaura coupling, palladium, photocatalyst, boronic acid, organic chemical, transformations.

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[1]
Miyaura, N.; Yamada, K.; Suzuki, A. A new stereospecific cross-coupling by the palladium catalyzed reaction of 1-alkenylboranes with 1-Alkenyl or 1-Alkynyl halides. Tetrahedron Lett., 1979, 20, 3437-3440.
[http://dx.doi.org/10.1016/S0040-4039(01)95429-2]
[2]
Wu, X-F.; Anbarasan, P.; Neumann, H.; Beller, M. From noble metal to Nobel Prize: Palladium-catalyzed coupling reactions as key methods in organic synthesis. Angew. Chem. Int. Ed. Engl., 2010, 49(48), 9047-9050.
[http://dx.doi.org/10.1002/anie.201006374] [PMID: 21031398]
[3]
Kostas, I.D. Suzuki-miyaura cross-coupling reaction and potential applications; MDPI: Basel, 2017. MDPI AG St. Alban-Anlage 66 Basel, Switzerland.
[4]
Hooshmand, S.E.; Heidari, B.; Sedghi, R.; Varma, R.S. Recent advances in the Suzuki–Miyaura cross-coupling reaction using efficient catalysts in eco-friendly media. Green Chem., 2019, 21, 381-405.
[http://dx.doi.org/10.1039/C8GC02860E]
[5]
Miyaura, N.; Suzuki, A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J. Chem. Soc. Chem. Commun., 1979, 866-867.
[http://dx.doi.org/10.1039/c39790000866]
[6]
Suzuki, A. Cross-coupling reactions via organoboranes. J. Organomet. Chem., 2002, 653, 83-90.
[http://dx.doi.org/10.1016/S0022-328X(02)01269-X]
[7]
Maluenda, I.; Navarro, O. Recent developments in the Suzuki-Miyaura reaction: 2010-2014. Molecules, 2015, 20(5), 7528-7557.
[http://dx.doi.org/10.3390/molecules20057528] [PMID: 25919276]
[8]
Hong, K.; Sajjadi, M.; Suh, J.M.; Zhang, K.; Nasrollahzadeh, M.; Jang, H.W.; Varma, R.S.; Shokouhimehr, M. Palladium nanoparticles on assorted nanostructured supports: Applications for suzuki, heck, and sonogashira cross–coupling reactions. ACS Appl. Nano Mater., 2020, 3, 2070-2103.
[http://dx.doi.org/10.1021/acsanm.9b02017]
[9]
Ohtaka, A. Recent progress of metal nanoparticle catalysts for c–c bond forming reactions. Catalysts, 2021, 11, 1266.
[http://dx.doi.org/10.3390/catal11111266]
[10]
Bhattacherjee, D.; Rahman, M.; Ghosh, S.; Bagdi, A.K.; Zyryanov, G.V.; Chupakhin, O.N.; Das, P.; Hajra, A. Advances in transition-metal catalyzed carbonylative suzuki-miyaura coupling reaction: An update. Adv. Synth. Catal., 2021, 363, 1597-1624.
[http://dx.doi.org/10.1002/adsc.202001509]
[11]
El-Maiss, J.; Dine, T.M.E.; Lu, C-S.; Karamé, I.; Kanj, A.; Polychronopoulou, K.; Shaya, J. Recent advances in metal-catalyzed Alkyl–Boron (C(sp3)–C(sp2)) suzuki-miyaura cross-couplings. Catalysts, 2020, 10, 296.
[http://dx.doi.org/10.3390/catal10030296]
[12]
Buchspies, J.; Szostak, M. Recent advances in acyl suzuki cross-coupling. Catalysts, 2019, 9, 53.
[http://dx.doi.org/10.3390/catal9010053]
[13]
Rocard, L.; Hudhomme, P. Recent developments in the suzuki–miyaura reaction using nitroarenes as electrophilic coupling reagents. Catalysts, 2019, 9, 213.
[http://dx.doi.org/10.3390/catal9030213]
[14]
Li, J.; Yang, S.; Wu, W.; Jiang, H. Recent advances in pd-catalyzed cross-coupling reaction in ionic liquids. Eur. J. Org. Chem., 2018, 2018, 1284-1306.
[http://dx.doi.org/10.1002/ejoc.201701509]
[15]
Roy, D.; Uozumi, Y. Recent advances in palladium-catalyzed cross-coupling reactions at ppm to ppb molar catalyst loadings. Adv. Synth. Catal., 2018, 360, 602-625.
[http://dx.doi.org/10.1002/adsc.201700810]
[16]
Chatterjee, A.; Ward, T.R. Recent advances in the palladium catalyzed suzuki–miyaura cross-coupling reaction in water. Catal. Lett., 2016, 146, 820-840.
[http://dx.doi.org/10.1007/s10562-016-1707-8]
[17]
Zhang, D.; Wang, Q. Palladium catalyzed asymmetric Suzuki–Miyaura coupling reactions to axially chiral biaryl compounds: Chiral ligands and recent advances. Coord. Chem. Rev., 2015, 286, 1-16.
[http://dx.doi.org/10.1016/j.ccr.2014.11.011]
[18]
Han, F-S. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: A remarkable advance from palladium to nickel catalysts. Chem. Soc. Rev., 2013, 42(12), 5270-5298.
[http://dx.doi.org/10.1039/c3cs35521g] [PMID: 23460083]
[19]
Manuel, M.; Cesar, J-S.; Jose, R.R. Recent advances in the heterogeneous palladium-catalysed suzuki cross-coupling reaction. Curr. Org. Chem., 2012, 16, 1128-1150.
[http://dx.doi.org/10.2174/138527212800564358]
[20]
Jana, R.; Pathak, T.P.; Sigman, M.S. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem. Rev., 2011, 111(3), 1417-1492.
[http://dx.doi.org/10.1021/cr100327p] [PMID: 21319862]
[21]
Bellina, F.; Carpita, A.; Rossi, R. Palladium catalysts for the suzuki cross-coupling reaction: An overview of recent advances. Synthesis, 2004, 15, 2419-2440.
[http://dx.doi.org/10.1055/s-2004-831223]
[22]
Li, X.H.; Baar, M.; Blechert, S.; Antonietti, M. Facilitating room-temperature suzuki coupling reaction with light: Mott−schottky photocatalyst for c−c coupling. Sci. Rep., 2013, 3, 1743.
[http://dx.doi.org/10.1038/srep01743]
[23]
Sarina, S.; Zhu, H.; Jaatinen, E.; Xiao, Q.; Liu, H.; Jia, J.; Chen, C.; Zhao, J. Enhancing catalytic performance of palladium in gold and palladium alloy nanoparticles for organic synthesis reactions through visible light irradiation at ambient temperatures. J. Am. Chem. Soc., 2013, 135(15), 5793-5801.
[http://dx.doi.org/10.1021/ja400527a] [PMID: 23566035]
[24]
Huang, X.; Li, Y.; Chen, Y.; Zhou, H.; Duan, X.; Huang, Y. Plasmonic and catalytic AuPd nanowheels for the efficient conversion of light into chemical energy. Angew. Chem. Int. Ed. Engl., 2013, 52(23), 6063-6067.
[http://dx.doi.org/10.1002/anie.201301096] [PMID: 23616428]
[25]
Wang, F.; Li, C.; Chen, H.; Jiang, R.; Sun, L-D.; Li, Q.; Wang, J.; Yu, J.C.; Yan, C-H. Plasmonic harvesting of light energy for Suzuki coupling reactions. J. Am. Chem. Soc., 2013, 135(15), 5588-5601.
[http://dx.doi.org/10.1021/ja310501y] [PMID: 23521598]
[26]
Hu, Y.X.; Liu, Y.Z.; Li, Z.; Sun, Y.G. Highly asymmetric, interfaced dimers made of Au nanoparticles and bimetallic nanoshells: Synthesis and photo-enhanced catalysis. Adv. Funct. Mater., 2014, 24, 2828-2836.
[http://dx.doi.org/10.1002/adfm.201303557]
[27]
Xiao, Q.; Sarina, S.; Jaatinen, E.; Jia, J.; Arnold, D.P.; Liu, H.; Zhu, H. Efficient photocatalytic suzuki cross-coupling reactions on Au–Pd alloy nanoparticles under visible light irradiation. Green Chem., 2014, 16, 4272-4285.
[http://dx.doi.org/10.1039/C4GC00588K]
[28]
Sarina, S.; Zhu, H.Y.; Xiao, Q.; Jaatinen, E.; Jia, J.; Huang, Y.; Zheng, Z.; Wu, H. Viable photocatalysts under solar-spectrum irradiation: Nonplasmonic metal nanoparticles. Angew. Chem. Int. Ed. Engl., 2014, 53(11), 2935-2940.
[http://dx.doi.org/10.1002/anie.201308145] [PMID: 24604813]
[29]
Mori, K.; Kawashima, M.; Yamashita, H. Visible-light-enhanced Suzuki-Miyaura coupling reaction by cooperative photocatalysis with an Ru-Pd bimetallic complex. Chem. Commun. (Camb.), 2014, 50(93), 14501-14503.
[http://dx.doi.org/10.1039/C4CC03682D] [PMID: 24943224]
[30]
Gao, S.; Shang, N.; Feng, C.; Wang, C.; Wang, Z. Graphene oxide–palladium modified Ag–AgBr: A visible-light-responsive photocatalyst for the Suzuki coupling reaction. RSC Advances, 2014, 4, 39242-39247.
[http://dx.doi.org/10.1039/C4RA05988C]
[31]
Wang, Z.J.; Ghasimi, S.; Landfester, K.; Zhang, K.A.I. Photocatalytic suzuki coupling reaction using conjugated microporous polymer with immobilized palladium nanoparticles under visible light. Chem. Mater., 2015, 27, 1921-1924.
[http://dx.doi.org/10.1021/acs.chemmater.5b00516]
[32]
Wen, M.; Takakura, S.; Fuku, K.; Mori, K.; Yamashita, H. Enhancement of Pd-catalyzed Suzuki–Miyaura coupling reaction assisted by localized surface plasmon resonance of Au nanorods. Catal. Today, 2015, 242, 381-385.
[http://dx.doi.org/10.1016/j.cattod.2014.05.019]
[33]
Trinh, T.T.; Sato, R.; Sakamoto, M.; Fujiyoshi, Y.; Haruta, M.; Kurata, H.; Teranishi, T. Visible to near-infrared plasmon-enhanced catalytic activity of Pd hexagonal nanoplates for the Suzuki coupling reaction. Nanoscale, 2015, 7(29), 12435-12444.
[http://dx.doi.org/10.1039/C5NR03841C] [PMID: 26133744]
[34]
Zhang, S.; Chang, C.; Huang, Z.; Ma, Y.; Gao, W.; Li, J.; Qu, Y. Visible-light-activated suzuki-miyaura coupling reactions of aryl chlorides over the multifunctional Pd/Au/porous nanorods of CeO2 catalysts. ACS Catal., 2015, 5, 6481-6488.
[http://dx.doi.org/10.1021/acscatal.5b01173]
[35]
Jiao, Z.; Zhai, Z.; Guo, X.; Guo, X-Y. Visible-light-driven photocatalytic Suzuki−Miyaura coupling reaction on Mott−Schottky-type Pd/SiC catalyst. J. Phys. Chem. C, 2015, 119, 3238-3243.
[http://dx.doi.org/10.1021/jp512567h]
[36]
Verma, P.; Kuwahara, Y.; Mori, K.; Yamashita, H. Synthesis and characterization of Pd/Ag bimetallic nanocatalyst on SBA-15 mesoporous silica as a plasmonic catalyst. J. Mater. Chem. A Mater. Energy Sustain., 2015, 3, 18889-18897.
[http://dx.doi.org/10.1039/C5TA04818D]
[37]
Cui, J.; Li, Y.; Liu, L.; Chen, L.; Xu, J.; Ma, J.; Fang, G.; Zhu, E.; Wu, H.; Zhao, L.; Wang, L.; Huang, Y. Near-infrared plasmonic-enhanced solar energy harvest for highly efficient photocatalytic reactions. Nano Lett., 2015, 15(10), 6295-6301.
[http://dx.doi.org/10.1021/acs.nanolett.5b00950] [PMID: 26373787]
[38]
Sun, D.; Li, Z. Double-solvent method to Pd nanoclusters encapsulated inside the cavity of NH2-Uio-66(Zr) for efficient visible-light-promoted suzuki coupling reaction. J. Phys. Chem. C, 2016, 120(35), 19744-19750.
[http://dx.doi.org/10.1021/acs.jpcc.6b06710]
[39]
Xie, A.; Zhang, K.; Wu, F.; Wang, N.; Wang, Y.; Wang, M. Polydopamine nanofilms as visible light-harvesting interfaces for palladium nanocrystal catalyzed coupling reactions. Catal. Sci. Technol., 2016, 6, 1764-1771.
[http://dx.doi.org/10.1039/C5CY01330E]
[40]
Li, Y.; Zhang, Z.; Pei, L.; Li, X.; Fan, T.; Ji, J.; Shen, J.; Ye, M. Multifunctional photocatalytic performances of recyclable Pd-NiFe2O4/reduced graphene oxide nanocomposites via different co-catalyst strategy. Appl. Catal. B, 2016, 190, 1-11.
[http://dx.doi.org/10.1016/j.apcatb.2016.02.054]
[41]
Lou, Z.; Gu, Q.; Liao, Y.; Yu, S.; Xue, C. Promoting Pd-catalyzed Suzuki coupling reactions through near-infrared plasmon excitation of WO3−x nanowires. Appl. Catal. B, 2016, 184, 258-263.
[http://dx.doi.org/10.1016/j.apcatb.2015.11.037]
[42]
Han, D.; Bao, Z.; Xing, H.; Yang, Y.; Ren, Q.; Zhang, Z. Fabrication of plasmonic Au-Pd alloy nanoparticles for photocatalytic Suzuki-Miyaura reactions under ambient conditions. Nanoscale, 2017, 9(18), 6026-6032.
[http://dx.doi.org/10.1039/C7NR01950E] [PMID: 28443911]
[43]
Raza, F.; Yim, D.; Park, J.H.; Kim, H-I.; Jeon, S-J.; Kim, J-H. Structuring Pd nanoparticles on 2H-WS2 nanosheets induces excellent photocatalytic activity for crosscoupling reactions under visible light. J. Am. Chem. Soc., 2017, 139(41), 14767-14774.
[http://dx.doi.org/10.1021/jacs.7b08619] [PMID: 28953384]
[44]
Shin, H.H.; Kang, E.; Park, H.; Han, T.; Lee, C-H.; Lim, D-K. Pd-nanodot decorated MoS2 nanosheets as a highly efficient photocatalyst for the visible-light-induced Suzuki–Miyaura coupling reaction. J. Mater. Chem. A Mater. Energy Sustain., 2017, 5, 24965-24971.
[http://dx.doi.org/10.1039/C7TA08441B]
[45]
Koohgard, M.; Hosseini-Sarvari, M. Enhancement of Suzuki–Miyaura coupling reaction by photocatalytic palladium nanoparticles anchored to TiO2 under visible light irradiation. Catal. Commun., 2018, 111, 10-15.
[http://dx.doi.org/10.1016/j.catcom.2018.03.026]
[46]
Chakraborty, J.; Nath, I.; Verpoort, F. Pd-nanoparticle decorated azobenzene based colloidal porous organic polymer for visible and natural sunlight induced Mott-Schottky junction mediated instantaneous Suzuki coupling. Chem. Eng. J., 2019, 358, 580-588.
[http://dx.doi.org/10.1016/j.cej.2018.09.037]
[47]
Wang, N.; Ma, L.; Wang, J.; Zhang, Y.; Jiang, R. Graphitic carbon nitride (g-C3 N4) supported palladium species: An efficient heterogeneous photocatalyst surpassing homogeneous thermal heating systems for suzuki coupling. ChemPlusChem, 2019, 84(8), 1164-1168.
[http://dx.doi.org/10.1002/cplu.201900360] [PMID: 31943962]
[48]
Feizpour, F.; Jafarpour, M.; Rezaeifard, A. Band gap modifcation of TiO2 nanoparticles by ascorbic acidstabilized Pd nanoparticles for photocatalytic Suzuki–Miyaura and ullmann coupling reactions. Catal. Lett., 2019, 149, 1595-1610.
[http://dx.doi.org/10.1007/s10562-019-02749-z]
[49]
Zhang, Y.; Zhang, L.; Zhang, X.; Yang, D.; Wan, L.; Au, C.; Chen, J.; Du, C.; Xie, M. Pyridine-based hypercrosslinked polymers as support for palladium photocatalysts and their application in Suzuki–Miyaura coupling reactions. New J. Chem., 2020, 44, 15202-15208.
[http://dx.doi.org/10.1039/D0NJ01675F]
[50]
Han, C.; Gómez, D.E.; Xiao, Q.; Xu, J. Near-field enhancement by plasmonic antennas for photocatalytic Suzuki-Miyaura cross-coupling reactions. J. Catal., 2021, 397, 205-211.
[http://dx.doi.org/10.1016/j.jcat.2021.03.020]
[51]
Choe, H.R.; Han, S.S.; Kim, Y-I.; Hong, C.; Cho, E.J.; Nam, K.M. Understanding and improving photocatalytic activity of Pd-Loaded BiVO4 microspheres: Application to visible light-induced suzuki-miyaura coupling reaction. ACS Appl. Mater. Interfaces, 2021, 13(1), 1714-1722.
[http://dx.doi.org/10.1021/acsami.0c15488] [PMID: 33369380]
[52]
Azadi, G.; Kazemi, F.; Firouzeh, E. Visible-light-driven photocatalytic Suzuki–Miyaura coupling reaction using novel retrievable magnetic photocatalyst. ChemistrySelect, 2021, 6, 630-639.
[http://dx.doi.org/10.1002/slct.202000978]

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