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New Morpholinoethyl-Substituted (NHC)PdBr2(3-Chloropyridine) Complexes: Synthesis, Characterization and Catalytic Activity in the Suzuki-Miyaura Reaction

Year 2019, , 374 - 380, 25.08.2019
https://doi.org/10.19113/sdufenbed.476479

Abstract

Recently,
chemists studying with organometallic compounds are increasingly interested in
Pd-PEPPSI complexes. This study contains the synthesis of the
2-morpholinoethyl-substituted Pd-PEPPSI complexes and their catalytic activity
in the Suzuki-Miyaura reaction. Synthesized the Pd-PEPPSI complexes have been
prepared from the 2-morpholinoethyl-substituted N-heterocyclic carbene (NHC)
precursors, palladium chloride and 3-chloropyridine. These complexes have been
characterized by using 1H NMR, 13C NMR, FTIR spectroscopy
and elementel analysis techniques. Also, synthesized the Pd-PEPPSI complexes
have been examined as catalysts in the Suzuki-Miyaura cross-coupling reaction
with arylboronic acid derivatives and have shown to exhibit well activity in
this reaction.

References

  • [1] Bertogg, A., Campanaovo, F., Togni, A., 2005. N‐Ferrocenyl‐Substituted Planar‐Chiral N‐Heterocyclic Carbenes and Their PdII Complexes. European Journal of Inorganic Chemistry, 2005(2), 347–356.
  • [2] Valente, C., Belowich, M.E., Hadei, N., Organ, M.G., 2010. Pd‐PEPPSI Complexes and the Negishi Reaction. European Journal of Inorganic Chemistry, 2010(23), 4343–4354.
  • [3] Aktaş, A., Akkoç, S. Gök, Y. 2013. Palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media. Journal of Coordination Chemistry, 66(16), 2901–2909.
  • [4] Cinderella, A.P., Vulovic, B., Watson, D.A., 2017. Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction. Journal of the American Chemical Society, 139(23), 7741–7744.
  • [5] Cordovilla, C., Bartolomé, C., Martínez-Ilarduya, J.M., Espinet P., 2015. The Stille Reaction, 38 Years Later. ACS Catalysis, 5(5), 3040−3053.
  • [6] Aktaş, A. Barut Celepci, D., Gök, Y., Aygün, M. 2018. 2-Hydroxyethyl-Substituted (NHC)Pd(II) PPh3 Complexes: Synthesis, Characterization, Crystal Structure and Its Application on Sonogashira Cross-Coupling Reactions in Aqueous Media. ChemistrySelect (3),10932– 10937.
  • [7] Osi´nska, M., Gniewek, A., Trzeciak, A.M., 2016. Suzuki–Miyaura, Hiyama coupling catalyzed by PEPPSI-type complexes with non-bulky NHC ligand. Journal of Molecular Catalysis A: Chemical, (418-419) C.S., Bhattacharyya, A., Hwang, W.S., Lin, I.J.B., 2009. Coinage Metal-N-Heterocyclic Carbene Complexes. Chemical Reviews, 109(8), 3561-3598.
  • [8] Sarı, Y., Aktaş, A., Barut Celepci, D., Gök, Y., Aygün, M., 2017. Synthesis, Characterization and Crystal Structure of New 2-Morpholinoethyl-Substituted Bis-(NHC)Pd(II) Complexes and the Catalytic Activity in the Direct Arylation Reaction. Catalysis Letters 147(9), 2340–2351.
  • [9] Gök, Y., Aktas, A., Erdoğan, H., Sarı, Y., 2018. New 4-vinylbenzyl-substituted bis(NHC)-Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction. Inorganica Chimica Acta, (471), 735–740.
  • [10] Chen, W.-X., Zhang, C.-Y., Lu, J.-M., 2013. Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalysed by N-heterocyclic carbene-palladium(II)-1-methylimi. Journal of Chemical Research, 37(10), 611-614.
  • [11] Poyatos, M., Mata, J.A., Peris, E., 2009. Complexes with Poly(N-heterocyclic carbene) Ligands: Structural Features and Catalytic Applications. Chemical Reviews, 109(8), 3677-3707.
  • [12] Díez-González, S., Marion, N., Nolan, S.P., 2009. N-Heterocyclic Carbenes in Late Transition Metal Catalysis. Chemical Reviews, 109(8), 3612–3676.
  • [13] Zhu, L., Ye, Y., Shao L., 2012. Well-defined NHC–Pd(II)–Im (NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C–N coupling of primary amines with aryl chlorides. Tetrahedron, 68(10), 2414–2420.
  • [14] Inomata, H., Toh, A., Mitsui, T., Fukuzawa, S., 2013. N-heterocyclic carbene copper(I) complex-catalyzed direct C–H thiolation of benzothiazoles. Tetrahedron Letters, 54(35), 4729–4731.
  • [15] Fortman, G.C., Nolan, S.P., 2011. N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. Chemical Society Reviews, 40(10), 5151–5169.
  • [16] Zhou, Z.-Z., Liu, F.-S., Shen, D.-S., Tan, C., Luo, L.-Y., 2011. Efficient palladium-catalyzed Suzuki cross-coupling reaction with β-ketoamine ligands. Inorganic Chemistry Communications, 14(5), 659–662.
  • [17] Polshettiwar, V., Decottignies, A., Len, C., Fihri, A., 2010. Suzuki-Miyaura Cross‐Coupling Reactions in Aqueous Media: Green and Sustainable Syntheses of Biaryls. ChemSusChem 3(5), 502–522.
  • [18] Benhamou, L., Besnar., C., Kündig, E.P., 2014. Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions. Organometallics, 33(1), 260−266.
  • [19] Aktaş, A., Barut Celepci, D., Gök, Y., Aygün, M. 2018. 2-Hydroxyethyl-Substituted Pd-PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki-Miyaura Reaction for Aryl Chlorides in Aqueous Media. ChemistrySelect (3), 9974–9980.
  • [20] Touj, N., Gürbüz, N., Hamdi, N., Yaşar, S., Özdemir, İ., 2018. Palladium PEPPSI complexes: Synthesis and catalytic activity on the Suzuki-Miyaura coupling reactions for aryl bromides at room temperature in aqueous media. Inorganica Chimica Acta, (478), 187–194.
  • [21] He, X.-X., Li, Y., Ma, B.-B., Ke, Z., Liu, F.-S., 2016. Sterically Encumbered Tetraarylimidazolium Carbene Pd-PEPPSI Complexes: Highly Efficient Direct Arylation of Imidazoles with Aryl Bromides under Aerobic Conditions. Organometallics, 35(16), 2655−2663.
  • [22] Özdemir, İ., Gök, Y., Gürbüz, N., Çetinkaya, E., Çetinkaya, B., 2004. Palladium‐catalyzed Suzuki reaction using 1,3‐dialkylbenzimidazol‐2‐ylidene ligands in aqueous media. Heteroat. Chem., 15(6), 419-423.
  • [23] Çekirdek, S., Yaşar, S., Özdemir, İ., 2014. Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application. Appl. Organomet. Chem., 28(6), 423-431.
  • [24] Aktaş, A., Keleştemur, Ü., Gök, Y., Balcıoğlu, S., Ateş, B., Aygün, M., 2018. Morpholino-ethyl‑substituted N‑heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties. J. Iran. Chem. Soc. 15, 131–139.
  • [25] Barbu, L., Popa, M.M., Shova, S., Ferbinteanu, M., Draghici, C., Dumitrascu, F., 2017. New Pd-NHC PEPPSI complexes from benzimidazolium salts with a phenacyl group attached to N3. Inorganica Chimica Acta, (463), 97–101.
  • [26] Seva, L., Hwang, W.S., Sabiah, S., 2016. Palladium biphenyl N-heterocyclic carbene complexes: Synthesis, structure and their catalytic efficiency in water mediated Suzuki–Miyaura cross-coupling reaction. Journal of Molecular Catalysis A: Chemical, (418-419), 125-131.
  • [27] Turkmen, H., Pelit, L., Cetinkaya, B., 2011. Water-soluble cis-[(NHC)PdBr2(TPPTS)] catalysts and their applications in Suzuki–Miyaura coupling of aryl chlorides. Journal of Molecular Catalysis A: Chemical, 348(1-2), 88–93.
  • [28] Shaughnessy, K.H., 2009. Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions. Chemistry Revviews. 109(2), 643–710.
  • [29] Schroeter, F., Soellner, J., Strassner. T., 2018. Cyclometalated Palladium NHC Complexes Bearing PEG Chains for Suzuki−Miyaura Cross-Coupling in Water. Organometallics 37(22), 4267−4275.
  • [30] Vishal, K., Fahlman, B.D., Sasidhar, B.S., Patil, S.A., Patil. S.A., 2017. Magnetic Nanoparticle-Supported N-Heterocyclic Carbene-Palladium(II): A Convenient, Efficient and Recyclable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions. Catal Lett 147(4), 900–918.
  • [31] Şahin, N., 2019. PEPPSI-type 2-methyl-2-propenyl-functionalized N-heterocyclic carbene-palladium complexes: Synthesis, structural characterization and catalytic activity on SuzukieMiyaura reaction. Journal of Molecular Structure 1177, 193-198.
  • [32] Shi, J.-C., Yu, H., Jiang, D., Yu, M., Huang, Y., Nong, L., Zhang, Q., Jin. Z., 2014. N-Heterocyclic Carbene Conjugated with Poly(ethylene glycol) for Palladium-Catalyzed Suzuki–Miyaura Coupling in Aqueous Solvents. Catal Lett 144(1), 158–164.

Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite

Year 2019, , 374 - 380, 25.08.2019
https://doi.org/10.19113/sdufenbed.476479

Abstract

Son
yıllarda, organometalik bileşiklerle çalışan kimyagerler, Pd-PEPPSI
komplekslerine daha fazla ilgi duymaktadırlar. Bu çalışma; 2-morfolinoetil
sübs-titüyeli Pd-PEPPSI komplekslerinin sentezini ve bunların Suzuki-Miyaura
çapraz-eşleşme reaksiyonundaki katalitik aktivitelerini içerir. Sentezlenen
Pd-PEPPSI kompleksleri; 2-morfolinoetil sübstitüyeli N-heterosiklik karben
(NHC) öncüleri, paladyum klorür ve 3-kloropiridin'den hazırlanmıştır. Bu
kompleksler, 1H NMR, 13C NMR, FTIR spektroskopisi ve
elementel analiz teknikleri kullanılarak karakterize edilmiştir. Ayrıca,
sentezlenen Pd-PEPPSI kompleksleri, Suzuki-Miyaura
çapraz-eşleşme
reaksiyonunda katalizör olarak incelenmiş ve bu reaksiyonda iyi aktivite
sergiledikleri gözlenmiştir.

References

  • [1] Bertogg, A., Campanaovo, F., Togni, A., 2005. N‐Ferrocenyl‐Substituted Planar‐Chiral N‐Heterocyclic Carbenes and Their PdII Complexes. European Journal of Inorganic Chemistry, 2005(2), 347–356.
  • [2] Valente, C., Belowich, M.E., Hadei, N., Organ, M.G., 2010. Pd‐PEPPSI Complexes and the Negishi Reaction. European Journal of Inorganic Chemistry, 2010(23), 4343–4354.
  • [3] Aktaş, A., Akkoç, S. Gök, Y. 2013. Palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media. Journal of Coordination Chemistry, 66(16), 2901–2909.
  • [4] Cinderella, A.P., Vulovic, B., Watson, D.A., 2017. Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction. Journal of the American Chemical Society, 139(23), 7741–7744.
  • [5] Cordovilla, C., Bartolomé, C., Martínez-Ilarduya, J.M., Espinet P., 2015. The Stille Reaction, 38 Years Later. ACS Catalysis, 5(5), 3040−3053.
  • [6] Aktaş, A. Barut Celepci, D., Gök, Y., Aygün, M. 2018. 2-Hydroxyethyl-Substituted (NHC)Pd(II) PPh3 Complexes: Synthesis, Characterization, Crystal Structure and Its Application on Sonogashira Cross-Coupling Reactions in Aqueous Media. ChemistrySelect (3),10932– 10937.
  • [7] Osi´nska, M., Gniewek, A., Trzeciak, A.M., 2016. Suzuki–Miyaura, Hiyama coupling catalyzed by PEPPSI-type complexes with non-bulky NHC ligand. Journal of Molecular Catalysis A: Chemical, (418-419) C.S., Bhattacharyya, A., Hwang, W.S., Lin, I.J.B., 2009. Coinage Metal-N-Heterocyclic Carbene Complexes. Chemical Reviews, 109(8), 3561-3598.
  • [8] Sarı, Y., Aktaş, A., Barut Celepci, D., Gök, Y., Aygün, M., 2017. Synthesis, Characterization and Crystal Structure of New 2-Morpholinoethyl-Substituted Bis-(NHC)Pd(II) Complexes and the Catalytic Activity in the Direct Arylation Reaction. Catalysis Letters 147(9), 2340–2351.
  • [9] Gök, Y., Aktas, A., Erdoğan, H., Sarı, Y., 2018. New 4-vinylbenzyl-substituted bis(NHC)-Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction. Inorganica Chimica Acta, (471), 735–740.
  • [10] Chen, W.-X., Zhang, C.-Y., Lu, J.-M., 2013. Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalysed by N-heterocyclic carbene-palladium(II)-1-methylimi. Journal of Chemical Research, 37(10), 611-614.
  • [11] Poyatos, M., Mata, J.A., Peris, E., 2009. Complexes with Poly(N-heterocyclic carbene) Ligands: Structural Features and Catalytic Applications. Chemical Reviews, 109(8), 3677-3707.
  • [12] Díez-González, S., Marion, N., Nolan, S.P., 2009. N-Heterocyclic Carbenes in Late Transition Metal Catalysis. Chemical Reviews, 109(8), 3612–3676.
  • [13] Zhu, L., Ye, Y., Shao L., 2012. Well-defined NHC–Pd(II)–Im (NHC=N-heterocyclic carbene; Im=1-methylimidazole) complex catalyzed C–N coupling of primary amines with aryl chlorides. Tetrahedron, 68(10), 2414–2420.
  • [14] Inomata, H., Toh, A., Mitsui, T., Fukuzawa, S., 2013. N-heterocyclic carbene copper(I) complex-catalyzed direct C–H thiolation of benzothiazoles. Tetrahedron Letters, 54(35), 4729–4731.
  • [15] Fortman, G.C., Nolan, S.P., 2011. N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. Chemical Society Reviews, 40(10), 5151–5169.
  • [16] Zhou, Z.-Z., Liu, F.-S., Shen, D.-S., Tan, C., Luo, L.-Y., 2011. Efficient palladium-catalyzed Suzuki cross-coupling reaction with β-ketoamine ligands. Inorganic Chemistry Communications, 14(5), 659–662.
  • [17] Polshettiwar, V., Decottignies, A., Len, C., Fihri, A., 2010. Suzuki-Miyaura Cross‐Coupling Reactions in Aqueous Media: Green and Sustainable Syntheses of Biaryls. ChemSusChem 3(5), 502–522.
  • [18] Benhamou, L., Besnar., C., Kündig, E.P., 2014. Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions. Organometallics, 33(1), 260−266.
  • [19] Aktaş, A., Barut Celepci, D., Gök, Y., Aygün, M. 2018. 2-Hydroxyethyl-Substituted Pd-PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki-Miyaura Reaction for Aryl Chlorides in Aqueous Media. ChemistrySelect (3), 9974–9980.
  • [20] Touj, N., Gürbüz, N., Hamdi, N., Yaşar, S., Özdemir, İ., 2018. Palladium PEPPSI complexes: Synthesis and catalytic activity on the Suzuki-Miyaura coupling reactions for aryl bromides at room temperature in aqueous media. Inorganica Chimica Acta, (478), 187–194.
  • [21] He, X.-X., Li, Y., Ma, B.-B., Ke, Z., Liu, F.-S., 2016. Sterically Encumbered Tetraarylimidazolium Carbene Pd-PEPPSI Complexes: Highly Efficient Direct Arylation of Imidazoles with Aryl Bromides under Aerobic Conditions. Organometallics, 35(16), 2655−2663.
  • [22] Özdemir, İ., Gök, Y., Gürbüz, N., Çetinkaya, E., Çetinkaya, B., 2004. Palladium‐catalyzed Suzuki reaction using 1,3‐dialkylbenzimidazol‐2‐ylidene ligands in aqueous media. Heteroat. Chem., 15(6), 419-423.
  • [23] Çekirdek, S., Yaşar, S., Özdemir, İ., 2014. Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application. Appl. Organomet. Chem., 28(6), 423-431.
  • [24] Aktaş, A., Keleştemur, Ü., Gök, Y., Balcıoğlu, S., Ateş, B., Aygün, M., 2018. Morpholino-ethyl‑substituted N‑heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties. J. Iran. Chem. Soc. 15, 131–139.
  • [25] Barbu, L., Popa, M.M., Shova, S., Ferbinteanu, M., Draghici, C., Dumitrascu, F., 2017. New Pd-NHC PEPPSI complexes from benzimidazolium salts with a phenacyl group attached to N3. Inorganica Chimica Acta, (463), 97–101.
  • [26] Seva, L., Hwang, W.S., Sabiah, S., 2016. Palladium biphenyl N-heterocyclic carbene complexes: Synthesis, structure and their catalytic efficiency in water mediated Suzuki–Miyaura cross-coupling reaction. Journal of Molecular Catalysis A: Chemical, (418-419), 125-131.
  • [27] Turkmen, H., Pelit, L., Cetinkaya, B., 2011. Water-soluble cis-[(NHC)PdBr2(TPPTS)] catalysts and their applications in Suzuki–Miyaura coupling of aryl chlorides. Journal of Molecular Catalysis A: Chemical, 348(1-2), 88–93.
  • [28] Shaughnessy, K.H., 2009. Hydrophilic Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions. Chemistry Revviews. 109(2), 643–710.
  • [29] Schroeter, F., Soellner, J., Strassner. T., 2018. Cyclometalated Palladium NHC Complexes Bearing PEG Chains for Suzuki−Miyaura Cross-Coupling in Water. Organometallics 37(22), 4267−4275.
  • [30] Vishal, K., Fahlman, B.D., Sasidhar, B.S., Patil, S.A., Patil. S.A., 2017. Magnetic Nanoparticle-Supported N-Heterocyclic Carbene-Palladium(II): A Convenient, Efficient and Recyclable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions. Catal Lett 147(4), 900–918.
  • [31] Şahin, N., 2019. PEPPSI-type 2-methyl-2-propenyl-functionalized N-heterocyclic carbene-palladium complexes: Synthesis, structural characterization and catalytic activity on SuzukieMiyaura reaction. Journal of Molecular Structure 1177, 193-198.
  • [32] Shi, J.-C., Yu, H., Jiang, D., Yu, M., Huang, Y., Nong, L., Zhang, Q., Jin. Z., 2014. N-Heterocyclic Carbene Conjugated with Poly(ethylene glycol) for Palladium-Catalyzed Suzuki–Miyaura Coupling in Aqueous Solvents. Catal Lett 144(1), 158–164.
There are 32 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Aydın Aktaş 0000-0001-8496-6782

Publication Date August 25, 2019
Published in Issue Year 2019

Cite

APA Aktaş, A. (2019). Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 23(2), 374-380. https://doi.org/10.19113/sdufenbed.476479
AMA Aktaş A. Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. August 2019;23(2):374-380. doi:10.19113/sdufenbed.476479
Chicago Aktaş, Aydın. “Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon Ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23, no. 2 (August 2019): 374-80. https://doi.org/10.19113/sdufenbed.476479.
EndNote Aktaş A (August 1, 2019) Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23 2 374–380.
IEEE A. Aktaş, “Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite”, Süleyman Demirel Üniv. Fen Bilim. Enst. Derg., vol. 23, no. 2, pp. 374–380, 2019, doi: 10.19113/sdufenbed.476479.
ISNAD Aktaş, Aydın. “Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon Ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23/2 (August 2019), 374-380. https://doi.org/10.19113/sdufenbed.476479.
JAMA Aktaş A. Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23:374–380.
MLA Aktaş, Aydın. “Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon Ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 23, no. 2, 2019, pp. 374-80, doi:10.19113/sdufenbed.476479.
Vancouver Aktaş A. Yeni Morfolinoetil-Sübstitüyeli (NHC)PdBr2(3-Kloropiridin) Kompleksleri: Sentez, Karakterizasyon ve Suzuki-Miyaura Reaksiyonundaki Katalitik Aktivite. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23(2):374-80.

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