Schiff base modified starch: A promising biosupport for palladium in Suzuki cross-coupling reactions

Kar, 2022, Green chemistry in the synthesis of pharmaceuticals, Chem. Rev., 122, 3637, 10.1021/acs.chemrev.1c00631 Shen, 2021, Nanoparticle-catalyzed green chemistry synthesis of polybenzoxazole, J. Am. Chem. Soc., 143, 2115, 10.1021/jacs.0c12488 Vásquez-Céspedes, 2021, Heterogeneous catalysis for cross-coupling reactions: an underutilized powerful and sustainable tool in the fine chemical industry?, Org. Process. Res. Dev., 25, 740, 10.1021/acs.oprd.1c00041 Zaera, 2022, Designing sites in heterogeneous catalysis: are we reaching selectivities competitive with those of homogeneous catalysts?, Chem. Rev., 122, 8594, 10.1021/acs.chemrev.1c00905 Baran, 2020, Cyanation of aryl halides and Suzuki-Miyaura coupling reaction using palladium nanoparticles anchored on developed biodegradable microbeads, Int. J. Biol. Macromol., 148, 565, 10.1016/j.ijbiomac.2020.01.157 Baran, 2019, Highly recoverable, reusable, cost-effective, and Schiff base functionalized pectin supported Pd(II) catalyst for microwave-accelerated Suzuki cross-coupling reactions, Int. J. Biol. Macromol., 127, 232, 10.1016/j.ijbiomac.2019.01.046 Baran, 2016, Microwave assisted synthesis of biarlys by C-C coupling reactions with a new chitosan supported Pd(II) catalyst, J. Mol. Struct., 1122, 111, 10.1016/j.molstruc.2016.05.091 Naeim, 2022, Palladium nanoparticles stabilized on the amino acids-functionalized Fe3O4 as the magnetically recoverable nanocatalysts for Heck and Suzuki reactions, Inorg. Chim. Acta, 542, 10.1016/j.ica.2022.121109 Khosravia, 2022, Efficient ullmann and Suzuki-Miyaura cross-coupling reactions catalyzed by heterogeneous pd-porous carbon beads catalysts in aqueous media, Sustain. Chem. Pharm., 30 Hafizi, 2022, Magnetically recyclable schiff-based palladium nanocatalyst [Fe3O4@SiNSB-Pd] and its catalytic applications in Heck reaction, Arab. J. Chem., 15, 10.1016/j.arabjc.2022.103914 Zhao, 2014, In situ formation of well-dispersed palladium nanoparticles immobilized in imidazolium-based organic ionic polymers, Chem. Commun., 50, 10871, 10.1039/C4CC04662E Rayadurgam, 2021, Palladium catalyzed C-C and C-N bond forming reactions: an update on the synthesis of pharmaceuticals from 2015–2020, Org. Chem. Front., 8, 384, 10.1039/D0QO01146K Wang, 2022, Enhancement of the catalytic activity of Suzuki coupling reactions by reduction of modified carriers and promotion of Pd/H2-PrxOy surface electron transfer, New J. Chem., 46, 14879, 10.1039/D2NJ02830A Li, 2022, Pd-Pd/PdO as active sites on intercalated graphene oxide modified by diaminobenzene: fabrication, catalysis properties, synergistic effects, and catalytic mechanism, RSC Adv., 12, 8600, 10.1039/D2RA00658H Liu, 2022, Pd clusters on schiff base-imidazole-functionalized MOFs for highly efficient catalytic Suzuki coupling reactions, Front. Chem., 10 Zhao, 2022, Highly efficient and recyclable amorphous Pd(II)/crystal Pd(0) catalyst for boosting Suzuki reaction in aqueous solution, Nano Res., 15, 1193, 10.1007/s12274-021-3623-5 Yu, 2021, One-pot synthesis of Pd/azo-polymer as an efficient catalyst for 4-nitrophenol reduction and Suzuki-Miyaura coupling reaction, Chem-Asian J., 16, 837, 10.1002/asia.202100002 Jaleh, 2021, Biopolymer-derived (nano)catalysts for hydrogen evolution via hydrolysis of hydrides and electrochemical and photocatalytic techniques: a review, Int. J. Biol. Macromol., 182, 1056, 10.1016/j.ijbiomac.2021.04.087 Nasrollahzadeh, 2021, Progresses in polysaccharide and lignin-based ionic liquids: catalytic applications and environmental remediation, J. Mol. Liq., 342, 10.1016/j.molliq.2021.117559 Schlemmer, 2021, Polysaccharides for sustainable energy storage-a review, Carbohydr. Polym., 265, 10.1016/j.carbpol.2021.118063 Salamatmanesh, 2020, Stabilizing Pd on magnetic phosphine-functionalized cellulose: DFT study and catalytic performance under deep eutectic solvent assisted conditions, Carbohyd. Polym., 235, 10.1016/j.carbpol.2020.115947 Tan, 2022, Separation of gallic acid from Cornus offcinalis and its interactions with corn starch, Int. J. Biol. Macromol., 208, 390, 10.1016/j.ijbiomac.2022.03.116 Intesaful Haque, 2022, The NADP-malate dehydrogenase (SmNADP-mdh), a C4 pathway gene from Suaeda monoica enhanced photosynthesis and biomass yield in C3 plants, Environmen. Exp. Bot., 201 Dhull, 2022, Lotus seed starch: a novel functional ingredient with promising properties and applications in food-a review, Starch-Starke, 74, 2200064, 10.1002/star.202200064 Rafiee, 2022, Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination, React. Funct. Polym., 170, 10.1016/j.reactfunctpolym.2021.105106 Baran, 2017, Practical, economical, and eco-friendly starch-supported palladium catalyst for Suzuki coupling reactions, J. Colloid Interf. Sci., 496, 446, 10.1016/j.jcis.2017.02.047 Sharma, 2017, Highly efficient magnetic Pd(0) nanoparticles stabilized by amine functionalized starch for organic transformations under mild conditions, Mol. Catal., 435, 58, 10.1016/j.mcat.2017.03.019 Panahi, 2017, Immobilized Pd nanoparticles on silica-starch substrate (PNP-SSS): efficient heterogeneous catalyst in buchwald-hartwig C-N cross coupling reaction, J. Organomet. Chem., 851, 210, 10.1016/j.jorganchem.2017.09.037 Kumar, 2019, Recent advances in the schiff bases and N-heterocyclic carbenes as ligands in the cross-coupling reactions: a comprehensive review, J. Heterocyclic Chem., 56, 1168, 10.1002/jhet.3504 Wang, 2018, Reusable N-heterocyclic carbene complex catalysts and beyond: a perspective on recycling strategies, Chem. Rev., 118, 9843, 10.1021/acs.chemrev.8b00057 Das, 2016, Schiff base-derived homogeneous and heterogeneous palladium catalysts for the Suzuki-Miyaura reaction, Coordin., Chem. Rev., 311, 1 Jia, 2015, Molecular assembly of Schiff base interactions: construction and application, Chem. Rev., 115, 1597, 10.1021/cr400559g Antony, 2019, A review on applications of chitosan-based Schiff bases, Int. J. Biol. Macromol., 129, 615, 10.1016/j.ijbiomac.2019.02.047 Yahya, 2022, Recycling Oryza sativa wastes into poly-imidazolium acetic acid-tagged nanocellulose schiff base supported Pd nanoparticles for applications in cross-coupling reactions, React. Funct. Polym., 170, 10.1016/j.reactfunctpolym.2021.105137 Dong, 2019, Design and synthesis of amine-functionalized cellulose with multiple binding sites and their application in C-C bond forming reactions, Int. J. Biol. Macromol., 130, 778, 10.1016/j.ijbiomac.2019.02.158 Dong, 2022, Palladium supported on pyrrole functionalized hypercrosslinked polymer: synthesis and its catalytic evaluations towards Suzuki-Miyaura coupling reactions in aqueous media, J. Mol. Liq., 368, 10.1016/j.molliq.2022.120679 Baran, 2015, Carboxymethyl chitosan Schiff base supported heterogeneous palladium(II) catalysts for Suzuki cross-coupling reaction, J. Mol. Catal. A-Chem., 407, 47, 10.1016/j.molcata.2015.06.008 Baran, 2015, Cu(II) and Pd(II) complexes of water soluble O-carboxymethyl chitosan Schiff bases: synthesis, characterization, Int. J. Biol. Macromol., 79, 542, 10.1016/j.ijbiomac.2015.05.021 Indarti, 2019, Wanrosli, silylation of TEMPO oxidized nanocellulose from oil palm empty fruit bunch by 3-aminopropyltriethoxysilane, Int. J. Biol. Macromol., 135, 106, 10.1016/j.ijbiomac.2019.05.161 Sharma, 2008, Optimizing acid-base bifunctional mesoporous catalysts for the Henry reaction: effects of the surface density and site isolation of functional groups, Langmuir, 24, 14306, 10.1021/la8030107 Baran, 2017, Construction of new biopolymer (chitosan)-based pincer-type Pd(II) complex and its catalytic application in Suzuki cross coupling reactions, J. Mol. Struct., 1134, 591, 10.1016/j.molstruc.2017.01.005 Baran, 2017, Design and application of sporopollenin microcapsule supported palladium catalyst: remarkably high turnover frequency and reusability in catalysis of biaryls, J. Colloid Interf. Sci., 486, 194, 10.1016/j.jcis.2016.09.071 Ziegler-Borowska, 2015, Thermal stability of magnetic nanoparticles coated by blends of modified chitosan and poly (quaternary ammonium) salt, J. Therm. Anal. Calorim., 119, 499, 10.1007/s10973-014-4122-7 Velásquez-Barreto, 2021, Relationships among molecular, physicochemical and digestibility characteristics of andean tuber starches, Int. J. Biol. Macromol., 182, 472, 10.1016/j.ijbiomac.2021.04.039 Fu, 2017, Nanopalladium on polyethylenimine-grafted starch: an efficient and ecofriendly heterogeneous catalyst for Suzuki-Miyaura coupling and transfer hydrogenation reactions, Appl. Organomet. Chem., 31, 10.1002/aoc.3853 Wu, 2020, Novel polyazamacrocyclic receptor impregnated macroporous polymeric resins for highly efficient capture of palladium from nitric acid media, Sep. Purif. Technol., 233, 10.1016/j.seppur.2019.115953 López-Magano, 2022, Predesigned covalent organic frameworks as effective platforms for Pd(II) coordination enabling cross-coupling reactions under sustainable conditions, Adv. Sustain. Syst., 6, 2100409, 10.1002/adsu.202100409 Liu, 2016, A simple, recyclable, and self-assembled palladium(II)-alkyl Schiff base complex for Suzuki coupling reaction: chain length dependence and heterogeneous catalysis, RSC Adv., 6, 84815, 10.1039/C6RA14864F Wang, 2020, Mechanical properties of basalt fiber improved by starch phosphates sizing agent, Appl. Surf. Sci., 521, 10.1016/j.apsusc.2020.146196 Ebrahimiasl, 2020, Copper-based schiff base complex immobilized on core-shell Fe3O4@SiO2 as a magnetically recyclable and highly efficient nanocatalyst for green synthesis of 2-amino-4H-chromene derivatives, Appl. Organomet. Chem., 34, 10.1002/aoc.5359 Dhali, 2022, Surface modification of the cellulose nanocrystals through vinyl silane grafting, Int. J. Biol. Macromol., 200, 397, 10.1016/j.ijbiomac.2022.01.079 Çalışkan, 2022, Design of a palladium nanocatalyst produced from Schiff base modified dialdehyde cellulose and its application in aryl halide cyanation and reduction of nitroarenes, Cellulose, 29, 4475, 10.1007/s10570-022-04550-5 Nuri, 2022, Pd nanoparticles stabilized on the cross-linked melamine-based SBA-15 as a catalyst for the Mizoroki-Heck reaction, Catal. Lett., 152, 991, 10.1007/s10562-021-03691-9 Pharande, 2021, Cellulose schiff base-supported Pd(II): an efficient heterogeneous catalyst for Suzuki Miyaura cross-coupling, Res. Chem. Intermediat., 47, 1, 10.1007/s11164-021-04528-1 Kandathil, 2019, From agriculture residue to catalyst support; A green and sustainable cellulose-based dip catalyst for C-C coupling and direct arylation, Carbohydr. Polym., 223, 115060, 10.1016/j.carbpol.2019.115060 Veisi, 2020, In situ decorated Pd NPs on chitosan-encapsulated Fe3O4/SiO2-NH2 as magnetic catalyst in Suzuki-miyaura coupling and 4-nitrophenol reduction, Carbohyd. Polym., 235, 10.1016/j.carbpol.2020.115966 Sun, 2020, Synthesis of a cellulosic Pd(salen)-type catalytic complex as a green and recyclable catalyst for cross-coupling reactions, Catal. Lett., 150, 2900, 10.1007/s10562-020-03172-5 Bi, 2019, The study and application of three highly porous hyper-crosslinked catalysts possessing similar catalytic centers, Polymer, 164, 183, 10.1016/j.polymer.2019.01.009 Lebaschi, 2017, Green synthesis of palladium nanoparticles mediated by black tea leaves (Camellia sinensis) extract: catalytic activity in the reduction of 4-nitrophenol and Suzuki-Miyaura coupling reaction under ligand-free conditions, J. Colloid Interf. Sci., 485, 223, 10.1016/j.jcis.2016.09.027 Mhaldar, 2020, Highly effective cellulose supported 2-aminopyridine palladium complex (Pd(II)-AMP-Cell@Al2O3) for Suzuki-Miyaura and Mizoroki-Heck cross coupling, React. Funct. Polym., 152, 10.1016/j.reactfunctpolym.2020.104586 Heidari, 2017, Magnetically separable and recyclable Fe3O4@SiO2/isoniazide/Pd nanocatalyst for highly efficient synthesis of biaryls by Suzuki coupling reactions, J. Colloid Interf. Sci., 501, 175, 10.1016/j.jcis.2017.04.054 Budarin, 2008, Palladium nanoparticles on polysaccharide-derived mesoporous materials and their catalytic performance in C-C coupling reactions, Green Chem., 10, 382, 10.1039/B715508E Rezapour, 2018, Palladium niacin complex immobilized on starch-coated maghemite nanoparticles as an efficient homo- and cross-coupling catalyst for the synthesis of symmetrical and unsymmetrical biaryls, Catal. Lett., 148, 3165, 10.1007/s10562-018-2513-2 Veisi, 2021, Ultrasound assisted synthesis of Pd NPs decorated chitosan-starch functionalized Fe3O4 nanocomposite catalyst towards Suzuki-Miyaura coupling and reduction of 4-nitrophenol, Int. J. Biol. Macromol., 172, 104, 10.1016/j.ijbiomac.2021.01.040