Generic placeholder image

Current Organic Chemistry

Author(s): Mohamed R. Shaaban*, Thoraya. A. Farghaly, Afaf Y. Khormi and Ahmad M. Farag

DOI: 10.2174/1385272823666190620121845

DownloadDownload PDF Flyer Cite As
Recent Advances in Synthesis and Uses of Heterocycles-based Palladium(II) Complexes as Robust, Stable, and Low-cost Catalysts for Suzuki- Miyaura Crosscouplings

Page: [1601 - 1662] Pages: 62

  • * (Excluding Mailing and Handling)

Abstract

C-C cross-couplings constitute the largest diversity of organic reactions of chemical, biomedical, and industrial significance. They are also among the most frequently encountered reactions used in the synthesis of numerous drugs and relevant pharmaceutical substances. Development of an easily accessed, efficient, stable, and low cost catalyst is an attractive area of research in such kind of organic synthesis. This review highlights the remarkable and recent achievements made recently in the synthesis and use of palladium(II) complexes catalysts, that are based on heterocycles as ligands in their constitution, in the Suzuki-Miyaura cross-coupling.

Keywords: Suzuki-Miyaura, cross-couplings, palladium(II) complexes, heterocycles, catalysis, biaryls.

Graphical Abstract

[1]
Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites. In: Fortschritte der Chemie organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products. Progress in the Chemistry of Organic Natural Products; Herz, W.; Falk, H.; Kirby, G.W.; Moore, R.E., Eds.; Springer: Vienna, 2001, Vol. 82, pp. 1-249.
[http://dx.doi.org/10.1007/978-3-7091-6227-9_1]
[2]
Horton, D.A.; Bourne, G.T.; Smythe, M.L. The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev., 2003, 103(3), 893-930.
[http://dx.doi.org/10.1021/cr020033s] [PMID: 12630855]
[3]
Guo, T.; Adang, A.E.P.; Dolle, R.E.; Dong, G.; Fitzpatrick, D.; Geng, P.; Ho, K.K.; Kultgen, S.G.; Liu, R.; McDonald, E.; McGuinness, B.F.; Saionz, K.W.; Valenzano, K.J.; Van Straten, N.C.R.; Xie, D.; Webb, M.L. Small molecule biaryl FSH receptor agonists. Part 1: Lead discovery via encoded combinatorial synthesis. Bioorg. Med. Chem. Lett., 2004, 14(7), 1713-1716.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.042] [PMID: 15026056]
[4]
Tomcufcik, A.; Child, R.; Sloboda, R. inventors; Wyeth Holdings Corp, assignee. Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain. U.S. Patent 3784701A, January 8,, 1970.
[5]
Buhlmayer, P.; Ostermayer, F.; Schmidlin, T. Acyl compounds. U.S. Patent 5399578, March 21,, 1995.
[6]
Hajduk, P.J.; Bures, M.; Praestgaard, J.; Fesik, S.W. Privileged molecules for protein binding identified from NMR-based screening. J. Med. Chem., 2000, 43(18), 3443-3447.
[http://dx.doi.org/10.1021/jm000164q] [PMID: 10978192]
[7]
Faghih, R.; Dwight, W.; Pan, J.B.; Fox, G.B.; Krueger, K.M.; Esbenshade, T.A.; McVey, J.M.; Marsh, K.; Bennani, Y.L.; Hancock, A.A. Synthesis and SAR of aminoalkoxy-biaryl-4-carboxamides: Novel and selective histamine H3 receptor antagonists. Bioorg. Med. Chem. Lett., 2003, 13(7), 1325-1328.
[http://dx.doi.org/10.1016/S0960-894X(03)00118-5] [PMID: 12657274]
[8]
Look, G.C.; Vacin, C.; Dias, T.M.; Ho, S.; Tran, T.H.; Lee, L.L.; Wiesner, C.; Fang, F.; Marra, A.; Westmacott, D.; Hromockyj, A.E.; Murphy, M.M.; Schullek, J.R. The discovery of biaryl acids and amides exhibiting antibacterial activity against gram-positive bacteria. Bioorg. Med. Chem. Lett., 2004, 14(6), 1423-1426.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.026] [PMID: 15006375]
[9]
Jefferson, Piperidine-containing β-arylpropionic acids as potent antagonists of αvβ3/αvβ5 integrins. Bioorg. Med. Chem. Lett., 2004, 14, 5257-5261.
[http://dx.doi.org/10.1016/j.bmcl.2004.08.033] [PMID: 15454207]
[10]
Wang, G.T.; Wang, S.; Gentles, R.; Sowin, T.; Leitza, S.; Reilly, E.B.; Von Geldern, T.W. Amino-substituted heterocycles as isosteres of trans-cinnamides: Design and synthesis of heterocyclic biaryl sulfides as potent antagonists of LFA-1/ICAM-1 binding. Bioorg. Med. Chem. Lett., 2005, 15(1), 195-201.
[http://dx.doi.org/10.1016/j.bmcl.2004.10.008] [PMID: 15582439]
[11]
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]
[12]
Diederich, F.; de Mejiere, A. Metal Catalyzed Cross-Coupling Reactions, 2nd ed; John Wiley & Sons: Weinheim, 2004.
[13]
Espinet, P.; Echavarren, A.M. The mechanisms of the stille reaction. Angew. Chem. Int. Ed. Engl., 2004, 43(36), 4704-4734.
[PMID: 15366073]
[14]
Cárdenas, D.J. Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions. Angew. Chem. Int. Ed. Engl., 2003, 42(4), 384-387.
[http://dx.doi.org/10.1002/anie.200390123] [PMID: 12569501]
[15]
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]
[16]
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]
[17]
Miyaura, N.; Yanagi, T.; Suzuki, A. The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases. Synth. Commun., 1981, 11, 513-519.
[http://dx.doi.org/10.1080/00397918108063618]
[18]
Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev., 1995, 95, 2457-2483.
[http://dx.doi.org/10.1021/cr00039a007]
[19]
Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organicelectrophiles, 1995-1998. J. Organomet. Chem., 1999, 576, 147-168.
[http://dx.doi.org/10.1016/S0022-328X(98)01055-9]
[20]
Suzuki, A. Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel Lecture). Angew. Chem. Int. Ed. Engl., 2011, 50(30), 6722-6737.
[http://dx.doi.org/10.1002/anie.201101379] [PMID: 21618370]
[21]
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]
[22]
Biajoli, A.F.P.; Schwalm, C.S.; Limberger, J.; Claudino, T.S.; Monteiro, A.L. Recent progress in the use of Pd-catalyzed C-C cross-coupling reactions in the synthesis of pharmaceutical compounds. J. Braz. Chem. Soc., 2014, 25, 2186-2214.
[http://dx.doi.org/10.5935/0103-5053.20140255]
[23]
Barnard, B.C. Palladium-catalysed C-C coupling: Then and now. Platin. Met. Rev., 2008, 52, 38-45.
[http://dx.doi.org/10.1595/147106708X256634]
[24]
Bellina, F.; Carpita, A.; Rossi, R. Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances. Synthesis, 2004, 2004(15), 2419-2440.
[http://dx.doi.org/10.1055/s-2004-831223]
[25]
Shibasaki, M.; Boden, C.D.; Kojima, A. The asymmetric Heck reaction. Tetrahedron, 1997, 53, 7371-7395.
[http://dx.doi.org/10.1016/S0040-4020(97)00437-7]
[26]
Laughlin, S.T.; Bertozzi, C.R. Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation. Nat. Protoc., 2007, 2(11), 2930-2944.
[http://dx.doi.org/10.1038/nprot.2007.422] [PMID: 18007630]
[27]
Zim, D.; Gruber, A.S.; Ebeling, G.; Dupont, J.; Monteiro, A.L. Sulfur-containing palladacycles: Efficient phosphine-free catalyst precursors for the Suzuki cross-coupling reaction at room temperature. Org. Lett., 2000, 2(18), 2881-2884.
[http://dx.doi.org/10.1021/ol0063048] [PMID: 10964389]
[28]
Botella, L.; Nájera, C. A convenient oxime-carbapalladacycle-catalyzed Suzuki cross-coupling of aryl chlorides in water. Angew. Chem. Int. Ed. Engl., 2002, 41(1), 179-181.
[http://dx.doi.org/10.1002/1521-3773(20020104)41:1<179:AID-ANIE179>3.0.CO;2-O] [PMID: 12491479]
[29]
Yang, D.; Chen, Y.C.; Zhu, N-Y. Sterically bulky thioureas as air- and moisture-stable ligands for pd-catalyzed Heck reactions of aryl halides. Org. Lett., 2004, 6(10), 1577-1580.
[http://dx.doi.org/10.1021/ol049697+] [PMID: 15128240]
[30]
Page, P.C.B.; Buckley, B.R.; Christie, S.D.; Edgar, M.; Poulton, A.M.; Elsegood, M.R.; McKee, V. A new paradigm in N-heterocyclic carbenoid ligands. Organomet. Chem., 2005, 690, 6210-6216.
[http://dx.doi.org/10.1016/j.jorganchem.2005.09.015]
[31]
Miura, M. Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling. Angew. Chem. Int. Ed. Engl., 2004, 43(17), 2201-2203.
[http://dx.doi.org/10.1002/anie.200301753] [PMID: 15108127]
[32]
Herrmann, W.A. N-heterocyclic carbenes: a new concept in organometallic catalysis. Angew. Chem. Int. Ed. Engl., 2002, 41(8), 1290-1309.
[http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1290:AID-ANIE1290>3.0.CO;2-Y] [PMID: 19750753]
[33]
Althagafi, I.I.; Shaaban, M.R.; Al-dawood, A.Y.; Farag, A.M. Novel pyridine-based Pd(II)-complex for efficient Suzuki coupling of aryl halides under microwaves irradiation in water. Chem. Cent. J., 2017, 11, 88-97.
[http://dx.doi.org/10.1186/s13065-017-0320-2]
[34]
Dawood, K.M.; Darweesh, A.F.; Shaaban, M.R.; Farag, A.M. Microwave-promoted Heck and Suzuki coupling reactions of new 3-(5-bromobenzofuranyl) pyrazole in aqueous media. ARKIVOC, 2018, 5, 348-358.
[35]
Dawood, K.M.; Elamin, M.B.; Farag, A.M. Microwave-assisted synthesis of 2-acetyl-5-arylthiophenes and 4-(5-arylthiophen-2-yl) thiazoles via Suzuki coupling in water. ARKIVOC, 2015, (7), 50-62.
[36]
Dawood, K.M.; Elamin, M.B.; Farag, A.M. Microwave-Assisted Synthesis of Arylated Pyrrolo[2,1-a] Isoquinoline Derivatives via Sequential [3 + 2] cycloadditions and suzuki-miyaura cross-couplings in aqueous medium. J. Heterocycl. Chem., 2016, 53(6), 1928-1934.
[http://dx.doi.org/10.1002/jhet.2508]
[37]
Dawood, K.M.; Shaaban, M.R.; Elamin, M.B.; Farag, A.M. Catalytic activity of some oxime-based Pd(II)-complexes in Suzuki coupling of aryl and heteroaryl bromides in water. Arab. J. Chem., 2017, 10(4), 473-479.
[http://dx.doi.org/10.1016/j.arabjc.2013.06.004]
[38]
Dawood, K.M.; Farag, A.M.; El-Deftar, M.M.; Gardiner, M.; Abdelaziz, H.A. Microwave-assisted synthesis of 5-arylbenzofuran-2-carboxylates via Suzuki coupling using 2-quinolinealdoxime-Pd(II)-complex. ARKIVOC, 2013, (3), 210-226.
[39]
Rao, K.U.; Appa, R.M.; Lakshmidevi, J.; Vijitha, R.; Rao, K.S.V.K.; Narasimhulu, M.; Venkateswarlu, K.C. (sp2)-C(sp2) Coupling in Water: Palladium(II) complexes of n-pincer tetradentate porphyrins as effective catalysts. Asian J. Org. Chem., 2017, 6(6), 751-757.
[http://dx.doi.org/10.1002/ajoc.201700068]
[40]
Zhang, G.; Luan, Y.; Han, X.; Wang, Y.; Wen, X.; Ding, C. Pd(L-proline)2 complex, an efficient catalyst for Suzuki-Miyaura coupling reaction in neat water. Appl. Organomet. Chem., 2014, 28(5), 332-336.
[http://dx.doi.org/10.1002/aoc.3129]
[41]
Layek, S. Anuradha; A., Bhumika; Pathak, D.D. Synthesis and characterization of a new Pd(II)-Schiff base complex [Pd(APD)2]: An efficient and recyclable catalyst for Heck-Mizoroki and Suzuki-Miyaura reactions. J. Organomet. Chem., 2017, 846, 105-112.
[http://dx.doi.org/10.1016/j.jorganchem.2017.05.049]
[42]
Shen, L.; Huang, S.; Nie, Y.; Lei, F. An efficient microwave-assisted Suzuki reaction using a new pyridine-pyrazole/Pd(II) species as catalyst in aqueous media. Molecules, 2013, 18(2), 1602-1612.
[http://dx.doi.org/10.3390/molecules18021602] [PMID: 23353128]
[43]
Ibrahim, M.B.; El Ali, B.; Fettouhi, M.; Ouahab, L.A. highly active palladium(II)-bis(oxazoline)catalyst for Suzuki-Miyaura, Mizoroki-Heck and Sonogashira coupling reactions in aqueous dimethylformamide. Appl. Organomet. Chem., 2015, 29(6), 400-407.
[http://dx.doi.org/10.1002/aoc.3305]
[44]
Potkin, V.I.; Bumagin, N.A.; Petkevich, S.K.; Lyakhov, A.S.; Rudakov, D.A.; Livantsov, M.V.; Golantsov, N.E. 5-(p-tolyl) isoxazol-3-amine-palladium(II) complex: preparation, structure, and catalytic application in the Suzuki-Miyaura reaction in water. Synthesis, 2012, 44(1), 151-157.
[http://dx.doi.org/10.1055/s-0031-1289618]
[45]
Baruah, J.; Gogoi, R.; Gogoi, N.; Borah, G. A thiosemicarbazone-palladium(II)-imidazole complex as an efficient pre-catalyst for Suzuki-Miyaura cross-coupling reactions at room temperature in aqueous media. Transition Metal Chem., 2017, 42(8), 683-692.
[http://dx.doi.org/10.1007/s11243-017-0174-4]
[46]
Liu, C.; Liu, G.; Zhao, H. a highly active Pd(ii) complex with 1-tritylimidazole ligand for Suzuki-miyaura and heck coupling reactions. Chin. J. Chem., 2016, 34(10), 1048-1052.
[http://dx.doi.org/10.1002/cjoc.201600272]
[47]
Szulmanowicz, M.S.; Zawartka, W.; Gniewek, A.; Trzeciak, A.M. Structure, dynamics and catalytic activity of Palladium(II) complexes with imidazole ligands. Inorg. Chim. Acta, 2010, 363(15), 4346-4354.
[http://dx.doi.org/10.1016/j.ica.2010.08.037]
[48]
Borkowski, T.; Zawartka, W.; Pospiech, P.; Mizerska, U.; Trzeciak, A. Reusable functionalized polysiloxane-supported Palladium catalyst for Suzuki-Miyaura cross-coupling. J. Catal., 2011, 282, 270-277.
[http://dx.doi.org/10.1016/j.jcat.2011.06.023]
[49]
Bumagin, N.A.; Kletskov, A.V.; Petkevich, S.K.; Kolesnik, I.A.; Lyakhov, A.S.; Ivashkevich, L.S.; Baranovsky, A.V.; Kurman, P.V.; Potkin, V.I. Substituted 1-(isoxazol-3-yl) methyl-1H-1,2,3-triazoles: Synthesis, palladium(II) complexes, and high-turnover catalysis in aqueous media. Tetrahedron, 2018, 74(27), 3578-3588.
[http://dx.doi.org/10.1016/j.tet.2018.05.016]
[50]
Kumar, S.; Saleem, F.; Singh, A.K. ‘Click’ generated 1,2,3-triazole based organosulfur/selenium ligands and their Pd(ii) and Ru(ii) complexes: Their synthesis, structure and catalytic applications. Dalton Trans., 2016, 45(28), 11445-11458.
[http://dx.doi.org/10.1039/C6DT01406B] [PMID: 27338234]
[51]
Mieczynska, E.; Borkowski, T.; Cypryk, M.; Pospiech, P.; Trzeciak, A.M. Palladium supported on triazolyl-functionalized polysiloxane as recyclable catalyst for Suzuki-Miyaura cross-coupling. Appl. Catal. A Gen., 2014, 470, 24-30.
[http://dx.doi.org/10.1016/j.apcata.2013.10.032]
[52]
Kong, F.; Zhou, C.; Wang, J.; Yu, Z.; Wang, R. Water-soluble Palladium click chelating complex: An efficient and reusable precatalyst for Suzuki-Miyaura and Hiyama reactions in water. ChemPlusChem, 2013, 78(6), 536-545.
[http://dx.doi.org/10.1002/cplu.201300067]
[53]
Bakherad, M.; Keivanloo, A.; Bahramian, B.; Jajarmi, S. Suzuki, Heck, and copper-free Sonogashira reactions catalyzed by 4-amino-5-methyl-3-thio-1,2,4-triazole-functionalized polystyrene resin-supported Pd(II) under aerobic conditions in water. J. Organomet. Chem., 2013, 724, 206-212.
[http://dx.doi.org/10.1016/j.jorganchem.2012.11.008]
[54]
Lasri, J.; MacLeod, T.C.O.; Pombeiro, A.J.L. Oxadiazoline and ketoimine palladium(II) complexes supported on a chitosan membrane and their catalytic activity for the microwave-assisted Suzuki-Miyaura cross-coupling in water. Appl. Catal. A Gen., 2011, 397(1-2), 94-102.
[http://dx.doi.org/10.1016/j.apcata.2011.02.019]
[55]
Fiebor, A.; Tia, R.; Makhubela, B.C.E.; Kinfe, H.H.B. Water-soluble SNS cationic palladium(II) complexes and their Suzuki-Miyaura cross-coupling reactions in aqueous medium. Beilstein J. Org. Chem., 2018, 14, 1859-1870.
[http://dx.doi.org/10.3762/bjoc.14.160] [PMID: 30112091]
[56]
Das, A.; Mishra, D.K.; Sinha, B.A. Pd(II) complex of a β-cyclodextrin-based polydentate ligand: An efficient catalyst for the Suzuki reaction in aqueous media. J. Coord. Chem., 2017, 70(17), 3035-3047.
[http://dx.doi.org/10.1080/00958972.2017.1378812]
[57]
Jerome, P.; Sathishkumar, P.N.; Bhuvanesh, N.S.P.; Karvembu, R. Towards phosphine-free Pd(II) pincer complexes for catalyzing Suzuki-Miyaura cross-coupling reaction in aqueous medium. J. Organomet. Chem., 2017, 845, 115-124.
[http://dx.doi.org/10.1016/j.jorganchem.2017.03.045]
[58]
Emre, H. M.; Yetkin, S. Microwave-assisted aqueous Suzuki coupling reactions catalyzed by ionic palladium(II) complexes. Transit. Metal Chem , 2012, (37), 109-116.
[http://dx.doi.org/10.1007/s11243-011-9564-1]
[59]
Baran. T. A new chitosan Schiff base supported Pd(II) complex for microwave-assisted synthesis of biaryls compounds. J. Mol. Struct., 2017, 1141, 535-541.
[http://dx.doi.org/10.1016/j.molstruc.2017.03.122]
[60]
Yadav, S.; Singh, A.; Rashid, N.; Ghotia, M.; Roy, T.K.; Ingole, P.P.; Ray, S.; Mobin, S.M.; Dash, C. Phosphine-Free bis(Pyrrolyl)pyridine based NNN-pincer Palladium(II) complexes as efficient catalysts for suzuki-miyaura cross-coupling reactions of aryl bromides in aqueous medium. Chem. Select, 2018, 3(32), 9469-9475.
[http://dx.doi.org/10.1002/slct.201801647]
[61]
nes, B.; SanMartin, R.; Moure, M.J.; Dominguez, E. Insights into the role of new palladium pincer complexes as robust and recyclable precatalysts for Suzuki-miyaura couplings in neat water. Adv. Synth. Catal., 2009, 351(13), 2124-2132.
[http://dx.doi.org/10.1002/adsc.200900345]
[62]
Ulusoy, M.; Oncel, N.; Aytar, E. Substituted 2-(2”-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki-Miyaura cross-coupling reactions. Turk. J. Chem., 2015, 39(6), 1289-1299.
[http://dx.doi.org/10.3906/kim-1505-105]
[63]
Prakash, O.; Joshi, H.; Sharma, K.N.; Sharma, A.K.; Singh, A.K. Catalytic synthesis of Bi- and teraryls in aqueous medium with palladium(II) complexes of 2-(Pyridine-2-ylmethylsulfanyl)benzoic acid. Eur. J. Inorg. Chem., 2015, 2015(3), 520-526.
[http://dx.doi.org/10.1002/ejic.201403003]
[64]
Mondal, P.; Banerjee, S.; Roy, A.S.; Mandal, T.K.; Islam, S.M. In situ prepared mesoporous silica nanosphere supported palladium(II) 2-aminopyridine complex catalyst for Suzuki-Miyaura cross-coupling reaction in water. J. Mater. Chem., 2012, 22(38), 20434-20442.
[http://dx.doi.org/10.1039/c2jm33835a]
[65]
Banik, B.; Tairai, A.; Shahnaz, N.; Das, P. Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki-Miyaura reactions in aqueous media. Tetrahedron Lett., 2012, 53(42), 5627-5630.
[http://dx.doi.org/10.1016/j.tetlet.2012.08.026]
[66]
Tu, T.; Feng, X.; Wang, Z.; Liu, X. A robust hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex: Synthesis and its catalytic application towards Suzuki-Miyaura couplings in aqueous solvents. Dalton Trans., 2010, 39(44), 10598-10600.
[http://dx.doi.org/10.1039/c0dt01083a] [PMID: 20941441]
[67]
Tu, T.; Malineni, J.; Doetz, K.H. A novel pyridine-bridged bis-benzimidazolylidene pincer palladium complex: Synthesis and catalytic properties. Adv. Synth. Catal., 2008, 350(11+12), 1791-1795.
[http://dx.doi.org/10.1002/adsc.200800244]
[68]
Liu, P.; Yan, M.; He, R. Bis(imino)pyridine palladium(II) complexes as efficient catalysts for the Suzuki-Miyaura reaction in water. Appl. Organomet. Chem., 2010, 24(2), 131-134.
[69]
Lee, D-H.; Lee, Y.H.; Kim, D.I.; Kim, Y.; Lim, W.T.; Harrowfield, J.M.; Thuery, P.; Jin, M-J.; Park, Y.C.; Lee, I-M. A highly effective azetidine-Pd(II) catalyst for Suzuki-Miyaura coupling reactions in water. Tetrahedron, 2008, 64(30-31), 7178-7182.
[http://dx.doi.org/10.1016/j.tet.2008.05.093]
[70]
Li, L.; Wu, T.; Wang, J.; Wang, R. Water-soluble ionic Palladium complexes: Effect of pendant ionic groups on palladium nanoparticles and suzuki-miyaura reaction in neat water. ChemPlusChem, 2014, 79(2), 257-265.
[http://dx.doi.org/10.1002/cplu.201300374]
[71]
Suzuka, T.; Adachi, M.; Yang, Z-S.; Ogihara, K.; Higa, M. Use of polymer-supported terpyridine palladium complex for Suzuki-Miyaura cross-coupling reaction in water and the synthesis of 2,6-disubstituted pyrimidines. Trans. Mater. Res. Soc. Jpn., 2013, 38(1), 119-122.
[http://dx.doi.org/10.14723/tmrsj.38.119]
[72]
Guo, Y.; Li, J.; Shi, X.; Liu, Y.; Xie, K.; Liu, Y.; Jiang, Y.; Yang, B.; Yang, R. Cyclodextrin-supported palladium complex: A highly active and recoverable catalyst for Suzuki-Miyaura cross-coupling reaction in aqueous medium. Appl. Organomet. Chem., 2017, 31(4)e3592
[http://dx.doi.org/10.1002/aoc.3592]
[73]
Baran, T.; Mentes, A. Microwave assisted synthesis of biaryls by C-C coupling reactions with a new chitosan supported Pd(II) catalyst. J. Mol. Struct., 2016, 1122, 111-116.
[http://dx.doi.org/10.1016/j.molstruc.2016.05.091]
[74]
Perumgani, P.C.; Kodicherla, B.; Mandapati, M.R.; Parvathaneni, S.P. Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex. Inorg. Chim. Acta, 2018, 477, 227-232.
[http://dx.doi.org/10.1016/j.ica.2018.03.006]
[75]
Sfahani, A.L.; Mohammadpoor-Baltork, I.; Mirkhani, V.; Khosropour, A.R.; Moghadam, M.; Tangestaninejad, S.; Kia, R. Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP): An efficient and reusable catalyst for Suzuki-Miyaura cross-coupling and Heck reactions. Adv. Synth. Catal., 2013, 355, 957-972.
[http://dx.doi.org/10.1002/adsc.201200707]
[76]
Sadhasivam, V.; Balasaravanan, R.; Chithiraikumar, C.; Siva, A. Incorporating Pd(OAc)2 on imine functionalized microporous covalent organic frameworks: A stable and efficient heterogeneous catalyst for Suzuki-Miyaura coupling in aqueous medium. Chem. Select, 2017, 2(3), 1063-1070.
[http://dx.doi.org/10.1002/slct.201601440]
[77]
Sobhani, S.; Zarifi, F. Pd-isatin Schiff base complex immobilized on γ-Fe2O3 as a magnetically recyclable catalyst for Heck and Suzuki cross-coupling reactions. Chin. J. Catal., 2015, 36, 555-563.
[http://dx.doi.org/10.1016/S1872-2067(14)60291-6]
[78]
Chidananda, V.K.B.; Ramakrishna, D.; Kaur, M.; Doddarevanna, R.H. Benzimidazolyl based Schiff base palladium complex in an ionic liquid: an effective combination for Suzuki coupling. J. Coord. Chem., 2017, 70(9), 1573-1584.
[http://dx.doi.org/10.1080/00958972.2017.1311412]
[79]
Li, H.; Wu, Y. Water-soluble 2-arylnaphthoxazole-derived palladium(II) complexes as phosphine-free catalysts for the Suzuki reaction in aqueous solvent. Appl. Organomet. Chem., 2008, 22(4), 233-236.
[http://dx.doi.org/10.1002/aoc.1379]
[80]
Kumar, S.; Ahmed, N. A facile approach for the synthesis of novel 1-oxa- and 1-aza-flavonyl-4-methyl-1H-benzo[d][1, 3] oxazin-2(4H)-ones by microwave enhanced Suzuki-Miyaura coupling using bidentate chromen-4-one-based Pd(II)-diimine complex as catalyst. RSC Advances, 2015, 5, 77075-77087.
[http://dx.doi.org/10.1039/C5RA15274G]
[81]
Gok, L.; Gunnaz, S.; Sahin, Z.S.; Pelit, L.; Turkmen, H. The imidazo[4,5-f][1,10]-phenanthrolinl-2-ylidene and its palladium complexes: Synthesis, characterization, and application in C-C cross-coupling reactions. J. Organomet. Chem., 2017, 827, 96-104.
[http://dx.doi.org/10.1016/j.jorganchem.2016.11.013]