2051-62-9Relevant articles and documents
Application of cyclic thiourea as an efficient ligand in palladium-catalyzed Hiyama cross-coupling reactions
Wu, Zhi-Sheng,Yang, Min,Li, Hong-Ling,Qi, Yan-Xing
, p. 1415 - 1419 (2008)
Cyclic thiourea has been first utilized as an efficient ligand in palladium-catalyzed Hiyama cross-coupling reactions. In the presence of palladium(II) acetate, N,N′-bis(2,5-di-tert-butylphenyl)-N,N′- ethylenethiourea, tetrabutylammonium fluoride, and dioxane, aryl halides (X = I, Br, Cl) underwent smooth cross coupling with trimethoxy(phenyl)silane to afford the corresponding biaryl products in moderate to excellent yields. Furthermore, the thiourea can be recovered by column chromatography and reused with negligible loss in catalytic activity. Georg Thieme Verlag Stuttgart.
Electrochemical synthesis and characterization of palladium nanoparticles on nafion-graphene support and its application for Suzuki coupling reaction
Shendage, Suresh S.,Patil, Umakant B.,Nagarkar, Jayashree M.
, p. 3457 - 3461 (2013)
The electrochemically deposited palladium nanoparticles on nafion-graphene support showed an excellent catalytic activity for Suzuki coupling reactions. The as obtained catalyst was characterized by SEM, TEM, EDAX, XRD, and TGA. The particle size of palladium nanoparticles (Pd NPs) determined from TEM was in the range of 4-12 nm. The mean diameter of Pd NPs was found to be 8.1 ± 1.9 nm. The recyclability of the catalyst was examined and it did not show any significant loss of catalytic activity for five consecutive cycles.
A highly stable and efficient magnetically recoverable and reusable Pd nanocatalyst in aqueous media heterogeneously catalysed Suzuki C-C cross-coupling reactions
Abbas Khakiani, Bahareh,Pourshamsian, Khalil,Veisi, Hojat
, p. 259 - 265 (2015)
Surface modification of Fe3O4 nanoparticles with triethoxyethylcyanide groups was used for the immobilization of palladium nanoparticles to produce Fe3O4/Ethyl-CN/Pd. The catalyst was characterized using Fourier transform infrared, wavelength-dispersive X-ray, energy-dispersive X-ray and X-ray photoelectron spectroscopies, field-emission scanning electron and transmission electron microscopies, and X-ray diffraction, vibrating sample magnetometry and inductively coupled plasma analyses. In this fabrication, cyano groups played an important role as a capping agent. The catalytic behaviour of Fe3O4/Ethyl-CN/Pd nanoparticles was measured in the Suzuki cross-coupling reaction of various aryl halides (Ar-I, Ar-Br, Ar-Cl) with phenylboronic acid in aqueous phase at room temperature. Interestingly, the novel catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled seven times without any significant loss in activity.
Green synthesis of palladium nanoparticles using Hibiscus sabdariffa L. flower extract: Heterogeneous and reusable nanocatalyst in Suzuki coupling reactions
Hekmati, Malak,Bonyasi, Fahimeh,Javaheri, Hadis,Hemmati, Saba
, (2017)
An elementary and ecological method has been designed for the biosynthesis of palladium nanoparticles, through the utilization of aqueous extract of red tea (Hibiscus sabdariffa L.) as a reducing and stabilizing agent. The nanoparticles obtained were characterized through UV–visible spectroscopy, transmission election microscopy, X-ray diffraction, Fourier transform infrared spectroscopy, scanning election microscopy, energy-dispersive X-ray analysis and inductively coupled plasma analysis. The nanoparticles with spherical shape and dimensions of approximately 10?nm were used as a heterogeneous catalyst for Suzuki coupling reactions under mild conditions. The high efficiency of the catalytic reaction was affirmed by the good yields of products, easy work-up, absence of palladium leached from the support and smooth recovery of catalyst.
Palladium anchored to SBA-15 functionalized with melamine-pyridine groups as a novel and efficient heterogeneous nanocatalyst for Suzuki-Miyaura coupling reactions
Veisi, Hojat,Hamelian, Mona,Hemmati, Saba
, p. 25 - 33 (2014)
The synthesis and characterization of an efficient and reusable catalyst, SBA-15/CCPy/Pd(II) nanocatalyst by grafting of melamine bearing pyridine groups on SBA-15 and subsequent generation of Pd nanoparticles, are described. The catalyst has been characterized by means of X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray (EDX), inductivity coupled plasma (ICP), nitrogen adsorption-desorption, and Fourier transform infrared (FTIR) spectroscopy. The catalyst is used in Suzuki cross-coupling reaction of various aryl halides, including less reactive chlorobenzene, and phenylboronic acid to give biaryls without any additive or ligand. These cross coupled products were produced in excellent yields under mild conditions at extremely low palladium loading (～0.3 mol%) with significantly high turnover frequencies (TOFs). The heterogeneous catalyst can be readily recovered by simple filtration and reused 7 times without significant loss in its activity.
Palladium biphenyl N-heterocyclic carbene complexes: Synthesis, structure and their catalytic efficiency in water mediated Suzuki-Miyaura cross-coupling reaction
Seva, Lavudi,Hwang, Wen-Shu,Sabiah, Shahulhameed
, p. 125 - 131 (2016)
Synthesis of bis-N-heterocyclic carbene ligand with biphenyl backbone [MIBIPhen](Br)2 (L), [Ag(MIBIPhen)]2(PF6)2 (1) and palladium-NHC complexes, [Pd(MIBIPhen)(Cl)(H3C-CN)]PF6 (2), [Pd(MIBIPhen)(H3C-CN)2](PF6)2 (3) and [Pd(MIBIPhen)Br2] (4) {MIBIPhen = (3,3′-(biphenyl-2,2′-diylbis(methylene))bis(1-methyl-1H-imidazol-3-ium)bromide)} is reported. All complexes (1-4) are characterized by NMR, ESI-MS, elemental analysis and single crystal XRD. Complex 1 serves as an efficient NHC transfer agent for the preparation of complex 2. Treatment of complex 2 with AgPF6 drives the exchange of chloride by acetonitrile to result in complex 3. Complex 4 is prepared by in situ deprotonation of MIBIPhen with Pd(OAc)2. Complex 1 is molecular box type with silver in bent geometry. Complexes 2, 3 & 4 exist as monomers with palladium in distorted-square-planar geometry. All Pd-NHC complexes are explored as catalyst in water mediated Suzuki-Miyaura cross coupling reaction where complex 3 shows efficient catalytic activity.
Pyridine mediated palladium acetate-catalysed dehalogenation of biaryl halides in ionic liquid system
Xin, Bingwei,Jia, Chunxiao,Qi, Zhixun
, p. 407 - 410 (2012)
The palladium acetate-catalysed dehalogenation of biaryl halides has been investigated in room temperature ionic liquids with pyridine acting as a co-solvent. The significant effect of pyridine in conjunction with Pd(OAc) 2 in [bmim][PF6] gave excellent results in the dehalogenation of biaryl iodines and bromides. The pyridine activated the C2-H of the imidazolium salt to be the source of hydrogen. The separation of desired product was easily performed by extraction with diethyl ether and the Pd(OAc)2-[bmim][PF6] system could be recycled five times with only a small decrease in activity. This procedure represents an environmentally friendly method for the preparation of biaryl compounds without the use of complex ligands.
Nickel(II) complexes with N,O-donor thiopseudourea ligands: Syntheses, structures, and catalytic applications in Kumada–Corriu cross-coupling reactions
Shakunthala, Kinche,Srivastava, Ankit Kumar,Babu, G. Narendra,Keesara, Srinivas,Pal, Samudranil
, (2021)
Synthesis, characterization, and physical properties of benzyl-N′-(4-R-benzoyl)-N-(2,6-diisopropylphenyl)carbamimidothioates, HL1 (R = H) and HL2 (R = Cl), and their nickel(II) complexes having the general molecular formula [Ni(L1/2)2] (1 and 2) have been reported. Elemental analysis, magnetic susceptibility, solution electrical conductivity, and various spectroscopic (IR, UV–Vis, and 1H NMR) measurements were used to characterize HL1, HL2, and the two complexes (1 and 2). The molecular structures of all four compounds were determined by single-crystal X-ray crystallographic studies. The structures of HL1 and HL2 showed the imino-ketone form of both compounds. In each of 1 and 2, the six-membered chelate ring forming iminolate-O and azomethine-N donor two (L1/2)? ligands form a square-planar trans-N2O2 coordination environment around the metal center. The spectroscopic characteristics of HL1, HL2, 1, and 2 are consistent with their molecular structures. Both complexes were successfully employed as efficient catalysts in Kumada–Corriu C-C cross-coupling reactions of aryl bromides with phenylmagnesium bromide. The reactions provided biaryl products in good to excellent yields with a good substrate scope.
A two-dimensional amide-linked covalent organic framework anchored Pd catalyst for Suzuki-Miyaura coupling reaction in the aqueous phase at room temperature
Wu, Shang,Ding, Ning,Jiang, Pengwei,Wu, Lan,Feng, Qiaoliang,Zhao, Lianbiao,Wang, Yanbin,Su, Qiong,Zhang, Hong,Yang, Quanlu
, (2020)
A two-dimensional amide-linked covalent organic frameworks (2D-COFs) supported Pd catalysis system was synthesized. Fourier transformed Infrared (FTIR), X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS) are used to characterize the prepared catalyst. Electron microscopes (SEM and TEM) are employed to know the morphologies of the synthesized catalysts. The catalyst is an efficient heterogeneous catalyst for Suzuki-Miyaura coupling reaction, exhibits high catalytic activity for various aryl halides and aryl boronic acids in aqueous media at room temperature. More importantly, the catalyst with high stability could be easily recycled for at least nine runs without decrease of the catalytic activity.
Highly Active Heterogeneous PdCl2/MOF Catalyst for Suzuki–Miyaura Cross-Coupling Reactions of Aryl Chloride
Gong, Xue-Fang,Zhang, Ling-Yan,Zhang, Hui-Xin,Cui, Yu-Meng,Jin, Fen-Chun,Liu, Yu,Zhai, Yu-Feng,Li, Jin-Heng,Liu, Gui-Yan,Zeng, Yong-Fei
, p. 1336 - 1341 (2020)
The exploration of highly efficient Pd/MOF heterogeneous catalyst system for the Suzuki–Miyaura cross-coupling (SMC) reactions of aryl chlorides is still challenging. Herein, a PdCl2/UiO-67-bpydc was successfully synthesized by immobilizing a low amount of PdCl2 onto the zirconium-based MOF (UiO-67-bpydc). PdCl2/UiO-67-bpydc showed excellent catalytic performance and good recycle ability for the SMC reaction of aryl chlorides under an ambient condition. Furthermore, PdCl2/UiO-67-bpydc retains the high catalytic activity even after five cycles, and exhibited excellent substrate size selectivity.
Dabco as an inexpensive and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
Li, Jin-Heng,Liu, Wen-Jie
, p. 2809 - 2811 (2004)
An inexpensive and highly efficient Pd(OAc)2/Dabco catalytic system has been developed for the cross-coupling of aryl halides with arylboronic acids. A combination of Pd(OAc)2 and Dabco (triethylenediamine) was observed to form an excellent catalyst, which affords high TONs (turnover numbers; TONs up to 950 000 for the reaction of Phl and p-chlorophenylboronic acid) for Suzuki-Miyaura cross-coupling of various aryl iodides and bromides with arylboronic acids.
Highly Active and Stable Palladium Nanoparticles Encapsulated in a Mesoporous Silica Yolk-Shell Nanoreactor for Suzuki-Miyaura Reactions
Wei, Fang,Cao, Changyan,Sun, Yongbin,Yang, Shuliang,Huang, Peipei,Song, Weiguo
, p. 2475 - 2479 (2015)
A yolk-shell nanoreactor with nitrogen-doped carbon spheres as the yolk and mesoporous silica (mSiO2) as the shell, together with Pd nanoparticles uniformly encapsulated in the void space, were prepared. They showed excellent catalytic activity and stability in the Suzuki-Miyaura reaction between bromobenzene and phenylboronic acid with 99% yield in 5 min. Core catalysis: A yolk-shell nanoreactor with nitrogen-doped carbon spheres as the yolk and mesoporous silica (mSiO2) as the shell, together with Pd nanoparticles uniformly encapsulated in the void space, showed excellent catalytic activity and stability in the Suzuki-Miyaura reaction. CTAB=Hexadecyl trimethyl ammonium bromide, PDA=Polydopamine, TEOS=Tetraethyl orthosilicate.
Highly efficient photocatalytic Suzuki coupling reaction by Pd3P/CdS catalyst under visible-light irradiation
Yang, Huai-Qing,Chen, Qian-Qian,Liu, Fulai,Shi, Rui,Chen, Yong
, p. 676 - 680 (2021)
Monodispersed palladium phosphide (Pd3P) (5.2 ± 0.5 nm) was firstly applied to photocatalytic Suzuki coupling reaction under visible light irradiation with CdS nanoflake as a photosensitizer. This heterogeneous system exhibited high yields to corresponding products and excellent stability in alcohol solvent at room temperature.
A novel magnetically recoverable palladium nanocatalyst containing organoselenium ligand for the synthesis of biaryls via Suzuki-Miyaura coupling reaction
Rangraz, Yalda,Nemati, Firouzeh,Elhampour, Ali
, (2020)
In the present work, a novel heterogeneous catalytic system involving palladium(II) complex as moisture- and air-stable organoselenium ligand supported on Fe3O4 nanoparticles modified by SiO2/azidopropyltriemethoxy silane was designed, synthesized and characterized using various physicochemical methods inclusive VSM, EDX, FE-SEM, TG, XRD, and FT-IR spectroscopy. The catalytic activity of the synthesized magnetic nanocatalyst which named Fe3O4@SiO2-T-Se/Pd(II) was evaluated in Suzuki-Miyaura coupling reactions for the preparation of corresponding biaryls using diverse aryl halides and arylboronic acids. The mild reaction conditions, variety of substrate scope, good yield, low reaction time, high stability, utilization of organoselenium compound as an air and moisture insensitive ligand and its immobilization on solid support, and more importantly effortless recovery and recyclability of the catalyst up to seven consecutive runs with no remarkable change in its activity are some of the interesting features of this protocol that makes it more beneficial from both industrial and environmental points of view.
Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions
Rajagopal,Jarikote, Dilip V.,Srinivasan
, p. 616 - 617 (2002)
Palladium catalyzed Suzuki cross-coupling reactions of halobenzenes including chlorobenzenes with phenylboronic acid have been achieved at ambient temperature (30°C) in the absence of a phosphine ligand using the ionic liquid 1,3-di-n-butylimidazolium tet
Microwave enhanced cross-coupling reactions involving potassium organotrifluoroborates
Kabalka, George W.,Al-Masum, Mohammad
, p. 6329 - 6331 (2005)
Palladium catalyzed coupling reactions of potassium aryltrifluoroborates with aryl iodides occur rapidly utilizing microwave irradiation. The coupled products are produced in excellent yields.
Palladium-guanidine complex immobilized on SBA-16: A highly active and recyclable catalyst for Suzuki coupling and alcohol oxidation
Yang, Hengquan,Han, Xiaojing,Ma, Zhancheng,Wang, Runqin,Liu, Jing,Ji, Xiangfei
, p. 441 - 451 (2010)
By immobilizing a mixture of a palladium-guanidine complex and guanidine on the mesoporous cage-like material SBA-16 via a one-pot silylation, we have successfully prepared a new solid catalyst for Suzuki coupling and the aerobic oxidation of alcohols. The structure and composition of the solid catalyst were characterized with N2 sorption, XRD, TEM, FT-IR and solid state NMR. The coordination state of the palladium-guanidine complex supported on the solid catalyst was preliminarily investigated with XPS and UV-vis spectroscopy. This catalyst afforded fast conversions for the Suzuki coupling of various aryl bromides and arylboronic acids in a 50% aqueous ethanol solution at 50 °C even at loadings of 0.01-0.001 mol%, and the TOF (turn-over frequency) for the Suzuki coupling of bromobenzene and arylboronic acids could be up to 45700 h-1 under mild conditions. A satisfactory yield was obtained even after the catalyst was reused several times. The developed solid catalyst combined with the mild conditions investigated represents one of the most efficient heterogeneous systems for the Suzuki coupling of bromides. Furthermore, it was found that the solid catalyst could also work well for the aerobic oxidation of benzylic alcohols and cinnamyl alcohol, affording over 99% selectivity. The catalyst could be reused 15 times without a significant decrease in activity and selectivity.
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Eliel,Daignault
, p. 2450,2451 (1965)
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Preparation of Ni-microsphere and Cu-MOF using aspartic acid as coordinating ligand and study of their catalytic properties in Stille and sulfoxidation reactions
Ghorbani-Choghamarani, Arash,Bastan, Hosna,Kakakhani, Zahra,Taherinia, Zahra
, p. 14905 - 14914 (2021)
In this study, the thermal and catalytic behavior of Ni-microsphere and Cu-MOF were investigated with aspartic acid as the coordinating ligand with different morphologies. The Ni-microsphere and Cu-MOF with aspartic acid, as the coordinating ligand, were prepared via a solvothermal method. The morphology and porosity of the obtained Ni microsphere and Cu-MOF were characterized by XRD, FTIR, TGA, DSC, BET and SEM techniques. The catalytic activity of the Ni-microsphere and Cu-MOF was examined in Stille and sulfoxidation reactions. The Ni microsphere and Cu-MOF were easily isolated from the reaction mixtures by simple filtration and then recycled four times without any reduction of catalytic efficiency.
A simple and efficient reusable polystyrene-supported palladium catalyst for Hiyama cross-coupling
Diebold, Carine,Derible, Antoine,Becht, Jean-Michel,Le Drian, Claude
, p. 264 - 267 (2013)
An efficient synthesis of biaryls using a Hiyama reaction between aryl iodides and aryltrialkoxysilanes in the presence of a diphenylphosphinomethylpolystyrene-supported palladium catalyst is described. The cross-coupling proceeds in the presence of only 0.1 mol % of supported palladium. The catalyst can be used at least four times and the palladium leaching is extremely low (ca. 1% of the initial amount).
In situ generation of palladium nanoparticles: Ligand-free palladium catalyzed ultrafast Suzuki-Miyaura cross-coupling reaction in aqueous phase at room temperature
Du, Zhengyin,Zhou, Wanwei,Wang, Fen,Wang, Jin-Xian
, p. 4914 - 4918 (2011)
An ultrafast and highly efficient ligand-free Suzuki-Miyaura cross-coupling reaction between aryl bromides/iodides and arylboronic acids using palladium chloride as catalyst in PEG400/H2O in air at room temperature has been developed. TEM showed that palladium nanoparticles were generated in situ from PdCl2/PEG400/H2O without use of other reductants. The catalyst system can be recycled to reuse three times with good yields.
Palladium-catalyzed denitrogenative cross-coupling of aryl halides with arylhydrazines under mild reaction conditions
Kempasiddaiah, Manjunatha,Kandathil, Vishal,Dateer, Ramesh B.,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.
, p. 273 - 281 (2021)
A greener approach for the synthesis of various functionalized biaryl frameworks in good to excellent yield through palladium-catalyzed denitrogenative cross-coupling of aryl halides with arylhydrazines under mild reaction conditions was developed. Catalytic system is free from the aid of expensive ligands and external oxidants. Biogenically prepared palladium nanoparticles (Pd NPs) immobilized cellulose based dip catalyst displayed excellent reactivity and selectivity toward the synthesis of a broad array of symmetrical and unsymmetrical biaryls through C–N bond cleavage in air as green oxidant. In addition, recyclability in denitrogenative cross-coupling reaction was also studied which showed excellent recycling performance and the dip catalyst remained stable even after several reuses. Thus, our newly developed strategy was successfully applied for constructing wide-ranging functional groups tolerated biaryls using arylhydrazines and aryl halides as coupling partners which is most useful for practical applications in synthetic chemistry.
Aqueous Suzuki coupling reaction catalyzed by water-soluble diimine/Pd(II) systems
Zhou, Jin,Guo, Xuming,Tu, Changzheng,Li, Xiaoyan,Sun, Hongjian
, p. 697 - 702 (2009)
A series of water-soluble diimine ligands were applied for the Suzuki reaction of arylbromide in different media. Low loading of catalyst (0.01 mol%) were necessary for the coupling reaction to proceed in water or water/ethanol. The catalytic system was found to tolerate a broad range of functional groups.
C-H arylation of unactivated arenes with aryl halides catalyzed by cobalt porphyrin
To, Ching Tat,Chan, Tek Long,Li, Bao Zhu,Hui, Ying Ying,Kwok, Tsz Yiu,Lam, Suet Yu,Chan, Kin Shing
, p. 1023 - 1026 (2011)
A general procedure for cobalt-catalyzed direct C-H arylation of unactivated arenes has been discovered. This method employs aryl halides as the direct coupling partners with arenes without using any Grignard-type reagents. This catalysis opens a new methodology for the preparation of symmetrical as well as unsymmetrical biaryls in a user-friendly approach.
An efficient catalyst- and base-free Suzuki-type coupling reaction
Yan, Jie,Zhou, Zhongshi,Zhu, Min
, p. 8173 - 8175 (2005)
Biaryls were prepared in good yields via a fast and efficient catalyst- and base-free Suzuki-type coupling reaction of sodium tetraphenylborate with iodanes in water at room temperature.
An environment-friendly dip-catalyst with xylan-based catalytic paper coatings
He, Mengyun,Qi, Haisong,Song, Tao,Xiang, Zhouyang
, (2021/10/12)
Replacing catalyst supports with sustainable and degradable materials is an urgent task. Xylan is a type of abundant natural polymers with potential applications in dispersing, anchoring, and coating materials, but its material values have always been underestimated. In this study, polyethyleneimine modified dialdehyde xylan (DAX-PEI) was used as a dispersing and anchoring agent to bind Pd nanoparticles onto paper surface to produce a DAX-PEI-Pd coated paper, which was used to catalyze Suzuki-Miyaura reactions. The catalytic coated paper exhibited a good catalytic activity with a yield of 91% and a high turnover frequency (TOF) of 3300 h?1. Besides, it showed an excellent recyclability with the same catalytic coated paper being used 15 times and still having a yield of nearly 90%. This environment-friendly catalytic coated paper owns its great prospect in organic synthesis.
Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold
Medina-Mercado, Ignacio,Porcel, Susana
, (2022/03/15)
A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.
Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media
Chahkamali, Farhad Omarzehi,Sansano, José Miguel,Sobhani, Sara
, (2021/11/10)
Abstract: Pd–N-heterocyclic carbine complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA, and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K4[Fe(CN)6]·3H2O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst confers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, ease of the catalyst recovery and reuse by magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles. Graphic Abstract: A new water dispersible heterogeneous Pd–N-heterocyclic carbene for the efficient fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water is developed.[Figure not available: see fulltext.].
