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The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions

Year 2018, , 133 - 148, 01.09.2017
https://doi.org/10.18596/jotcsa.341530

Abstract

A range of iminophosphine (PN) ligands ((C6H5)2P-C6H4-CH=NR
(R=-C6H3(2-CH3)(4-OH) (1a), -CH2CH2C6H4(4-OH)
(1b) and -C5H3N(2-CH3)
(1c))  have been synthesized starting from 4-amino-3-methylphenol,
4-(2-aminoethyl)phenol and 2-amino-3-methylpyridine with 2-(diphenylphosphino)benzaldehyde.
The PN ligands were reacted with Pd(cod)Cl2 to give corresponding new
PdLCl2 metal complexes, (2a,
2b and 2c).
The Heck and Suzuki C-C coupling reactions were examined with
catalysts 2a-2c and showed high conversions under the determined conditions with
para substituted arylhalides

References

  • 1. Aydemir, M., Baysal, A., Gümgüm, B., Synthesis and characterization of tris{2-(N,N-bis(diphenylphosphino) aminoethyl} amine derivatives: Application of a palladium(II) complex as a pre-catalyst in the Heck and Suzuki cross-coupling reactions. J. Organomet. Chem. 2008; 693: 3810-3814.
  • 2. Scrivanti, A., Beghetto, V., Matteoli, U., Antonaroli, S., Marini, A., Crociani, B., Catalytic activity of η2-(olefin)palladium(0) complexes with iminophosphine ligands in the Suzuki–Miyaura reaction. Role of the olefin in the catalyst stabilization. Tetrahedron 2005; 61: 9752-9758.
  • 3. Nadri, S., Joshaghani, M., Rafiee, E., Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki–Heck reaction. Applied Catal. A, 2009; 362: 163-168.
  • 4. Iranpoor, N., Firouzabadi, H., Motevalli, S., Talebi, M., Palladium nanoparticles supported on silicadiphenyl phosphinite (SDPP) as efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions. J. Organomet. Chem. 2012; 708: 118-124.
  • 5. Iyer, S., Kulkarni, G.M., Ramesh, C., Mizoroki–Heck reaction, catalysis by nitrogen ligand Pd complexes and activation of aryl bromides. Tetrahedron, 2004; 60: 2163-2172.
  • 6. Gruber, A. S., Zim, D., Ebeling, G., Monteiro, A.L., Dupont, J., Sulfur-Containing Palladacycles as Catalyst Precursors for the Heck Reaction. Org. Lett. 2000; 2: 1287-1290.
  • 7. Doherty, S., Knight, J.G., Tom, H., Scanlan, T. H., Elsegood, M. R. J., Clegg,W., Iminophosphines: synthesis, formation of 2,3-dihydro-1H-benzo[1,3]azaphosphol-3-ium salts and N-(pyridin-2-yl)-2-diphenylphosphinoylaniline, coordination chemistry and applications in platinum group catalyzed Suzuki coupling reactions and hydrosilylations. J. Organomet. Chem. 2002; 650: 231-248.
  • 8. Cheng, J., Wang, F., Xu, J. H., Pan, Y., Zhang, Z., Palladium-catalyzed Suzuki–Miyaura reaction using aminophosphine as ligand. Tetrahedron Lett. 2003; 44: 7095-7098.
  • 9. Drew, D., Doyle, J. R., Cyclic diolefin complexes of platinum and palladium. Inorg. Synth. 1990; 28: 346-347.
  • 10. Laue, S., Greiner, L., Wöltinger, J., Liese, A., Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone. Advan. Synt.& Catal. 2001; 343: 711-720.
  • 11. Keleş, M., Şahinoğlu, C., Emir, D. M., Mart, M., New iminophosphine–Ru(II) complexes and their application in hydrogenationand transfer hydrogenation. Appl. Organometal. Chem. 2014; 28: 768-772.
  • 12. Monteiro, A .L., Nobre, S. M., Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki–Miyaura cross-coupling reactions under mild conditions. J. Mol. Catal. A 2009; 313: 65-73.
  • 13. Jeffrey, J.C., Rauchfuss, T. B., Tucker, P.A., Metal Complexes of Diiminodiphosphines. Structural and Reactivity Patterns. Inorg. Chem. 1980; 19: 3306-3315.
  • 14. Rulke, R. E., Kaasjager, V. E., Wehman, P., Elsevir, C. J., Leeuwen, P. W., Vrieze, K., Stable Palladium(0), Palladium(II), and Platinum(II) Complexes Containing a New, Multifunctional and Hemilabile Phosphino−Imino−Pyridyl Ligand:  Synthesis, Characterization, and Reactivity.Organomet. 1996; 15: 3022-3031.
  • 15. Crochet, P., Gimeno, J., Borge, J., Garcia-Granda, S., Novel ruthenium(II) complexes containing imino- or aminophosphine ligands for catalytic transfer hydrogenation. New J. Chem. 2003; 27: 414-420.
  • 16. Kwong, H. L., Lee, W. S., Lai, T. S., Wong, W. T., Ruthenium catalyzed asymmetric transfer hydrogenation based on chiral P,N,O Schiff base ligands and crystal structure of a ruthenium(II) complex bearing chiral P,N,O Schiff base ligands. Inorg. Chem. Com. 1999; 2: 66-69.
  • 17. Reddy, K.R., Surekha, K., Lee, G. H., Peng, S.M., Chen, J.T., Liu, S.T., Study of Insertion of Olefins and/or Carbon Monoxide into Phosphine−Imine Palladium Methyl Complexes. Organometallics, 2001; 20: 1292-1299.
  • 18. Wang, C., Friedrich, S., Youkin, T. R., Li, R. T., Grubbs, R. H., Bansleben, D. A., Day, M. W., Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization. Organomet. 1998; 17: 3149-3151.
  • 19. Lavery, A., Nelson, S. M., Dinuclear intermediates in the oxidation of pendant olefinic groups of palladium(II)-co-ordinated Schiff-base ligands. J. Chem. Soc. Dalt Trans. 1984; 0: 615-620.
  • 20. Flower, K. R., Alder, M.J., Cross, W. I., Pritchard, R. G., Azo-phosphine containing complexes of Group 6 metal carbonyls: crystal and molecular structure of [Mo(CO)5{1-(4-ethylphenylazo)-6-diphenylphosphino-naphthalen-2-ol}]. J. Organomet. Chem., 1998; 568: 279-285.
  • 21. Gavrilov, K. N., Korostylev, A.V., Bondarev, O.G., Lyubimov, S. Y., Kovalevsky, A. Y., Petrovskii, P. V., Davankov, V. A., New palladium(II) complexes of (N,N-dimethylamino)alkoxy-1,3,2-oxazaphospholidine ligands. Inorg.Chim. Acta, 2000; 303: 1-6.
  • 22. Smith, G. S., Mahamo, T., Mogorosi,M. M., Moss, J. R., Mapolie, S. F., Slootweg, J.C., Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts. J. Organomet.Chem. 2012; 703: 34-42.
  • 23. Andjelkovic, K., Radulovic, V., Bacchi, A., Pelizzi, G., Sladic, D., Brceski, I., Synthesis, Structure, and Antimicrobial Activity of Complexes of Pt(II), Pd(II), and Ni(II) with the Condensation Product of 2-(Diphenylphosphino)benzaldehyde and Semioxamazide. Mon. Chem.Chem. Monthly, 2006; 137: 681-691.
  • 24. Smith,G.S., Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C.,Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene. J. Organomet. Chem. 2011; 696: 3585-3592.
  • 25. Keleş¸ M., Yılmaz, M.K., Palladium (II) complexes with aminomethylphosphine ligands as catalysts for the heck reaction. Heteroatom Chem., 2012; 23: 466-471.
  • 26. Serindağ, O., Aydın, Z., Keleş, M., Synthesis of palladium complexes with bis (diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate. J. Organomet. Chem. 2007; 692: 1951-1955.
  • 27. Garrau, P.E., DELTA.R-ring contributions to phosphorus-31 NMR parameters of transition-metal-phosphorus chelate complexes. Chem. Rev. 1981; 81: 229-266.
  • 28. Smith, R.C., Bodner, C. R., Earl, M.J., Sears, N.C., Hill, N. E., Bishop, L.M., Sizemore, N.,Hehemann, D.T., Bohn, J.J., Protasiewiez, J. D., Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines. J. Organomet. Chem. 2005; 690: 477-481. DOI:
  • 29. Pramick, M. R., Rosemeier, S. M., Beranek, M. T., Nickse, S. B., Stone, J. J., Stockland, R.A., Baldwin, Kastner, S.M. M.E., Coupling of Aryl Halides with Aryl Boronic Acids with P (C6H5)(2-C6H4Cl) 2 as the Supporting Ligand. Organomet. 2003; 22: 523-528.
  • 30. Harrington, P.J., Lodewijk, E., Twenty years of naproxen technology. Org. Process Res. Dev. 1997; 1: 72-76.
  • 31. Sabounchei, S. J., Panahimehr, M., Ahmadi, M., Nasri, Z., . Khavasi, H.R., Four-coordinate Pd (II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction. J. Organomet. Chem. 2013; 723: 207-213.
Year 2018, , 133 - 148, 01.09.2017
https://doi.org/10.18596/jotcsa.341530

Abstract

References

  • 1. Aydemir, M., Baysal, A., Gümgüm, B., Synthesis and characterization of tris{2-(N,N-bis(diphenylphosphino) aminoethyl} amine derivatives: Application of a palladium(II) complex as a pre-catalyst in the Heck and Suzuki cross-coupling reactions. J. Organomet. Chem. 2008; 693: 3810-3814.
  • 2. Scrivanti, A., Beghetto, V., Matteoli, U., Antonaroli, S., Marini, A., Crociani, B., Catalytic activity of η2-(olefin)palladium(0) complexes with iminophosphine ligands in the Suzuki–Miyaura reaction. Role of the olefin in the catalyst stabilization. Tetrahedron 2005; 61: 9752-9758.
  • 3. Nadri, S., Joshaghani, M., Rafiee, E., Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki–Heck reaction. Applied Catal. A, 2009; 362: 163-168.
  • 4. Iranpoor, N., Firouzabadi, H., Motevalli, S., Talebi, M., Palladium nanoparticles supported on silicadiphenyl phosphinite (SDPP) as efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions. J. Organomet. Chem. 2012; 708: 118-124.
  • 5. Iyer, S., Kulkarni, G.M., Ramesh, C., Mizoroki–Heck reaction, catalysis by nitrogen ligand Pd complexes and activation of aryl bromides. Tetrahedron, 2004; 60: 2163-2172.
  • 6. Gruber, A. S., Zim, D., Ebeling, G., Monteiro, A.L., Dupont, J., Sulfur-Containing Palladacycles as Catalyst Precursors for the Heck Reaction. Org. Lett. 2000; 2: 1287-1290.
  • 7. Doherty, S., Knight, J.G., Tom, H., Scanlan, T. H., Elsegood, M. R. J., Clegg,W., Iminophosphines: synthesis, formation of 2,3-dihydro-1H-benzo[1,3]azaphosphol-3-ium salts and N-(pyridin-2-yl)-2-diphenylphosphinoylaniline, coordination chemistry and applications in platinum group catalyzed Suzuki coupling reactions and hydrosilylations. J. Organomet. Chem. 2002; 650: 231-248.
  • 8. Cheng, J., Wang, F., Xu, J. H., Pan, Y., Zhang, Z., Palladium-catalyzed Suzuki–Miyaura reaction using aminophosphine as ligand. Tetrahedron Lett. 2003; 44: 7095-7098.
  • 9. Drew, D., Doyle, J. R., Cyclic diolefin complexes of platinum and palladium. Inorg. Synth. 1990; 28: 346-347.
  • 10. Laue, S., Greiner, L., Wöltinger, J., Liese, A., Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone. Advan. Synt.& Catal. 2001; 343: 711-720.
  • 11. Keleş, M., Şahinoğlu, C., Emir, D. M., Mart, M., New iminophosphine–Ru(II) complexes and their application in hydrogenationand transfer hydrogenation. Appl. Organometal. Chem. 2014; 28: 768-772.
  • 12. Monteiro, A .L., Nobre, S. M., Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki–Miyaura cross-coupling reactions under mild conditions. J. Mol. Catal. A 2009; 313: 65-73.
  • 13. Jeffrey, J.C., Rauchfuss, T. B., Tucker, P.A., Metal Complexes of Diiminodiphosphines. Structural and Reactivity Patterns. Inorg. Chem. 1980; 19: 3306-3315.
  • 14. Rulke, R. E., Kaasjager, V. E., Wehman, P., Elsevir, C. J., Leeuwen, P. W., Vrieze, K., Stable Palladium(0), Palladium(II), and Platinum(II) Complexes Containing a New, Multifunctional and Hemilabile Phosphino−Imino−Pyridyl Ligand:  Synthesis, Characterization, and Reactivity.Organomet. 1996; 15: 3022-3031.
  • 15. Crochet, P., Gimeno, J., Borge, J., Garcia-Granda, S., Novel ruthenium(II) complexes containing imino- or aminophosphine ligands for catalytic transfer hydrogenation. New J. Chem. 2003; 27: 414-420.
  • 16. Kwong, H. L., Lee, W. S., Lai, T. S., Wong, W. T., Ruthenium catalyzed asymmetric transfer hydrogenation based on chiral P,N,O Schiff base ligands and crystal structure of a ruthenium(II) complex bearing chiral P,N,O Schiff base ligands. Inorg. Chem. Com. 1999; 2: 66-69.
  • 17. Reddy, K.R., Surekha, K., Lee, G. H., Peng, S.M., Chen, J.T., Liu, S.T., Study of Insertion of Olefins and/or Carbon Monoxide into Phosphine−Imine Palladium Methyl Complexes. Organometallics, 2001; 20: 1292-1299.
  • 18. Wang, C., Friedrich, S., Youkin, T. R., Li, R. T., Grubbs, R. H., Bansleben, D. A., Day, M. W., Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization. Organomet. 1998; 17: 3149-3151.
  • 19. Lavery, A., Nelson, S. M., Dinuclear intermediates in the oxidation of pendant olefinic groups of palladium(II)-co-ordinated Schiff-base ligands. J. Chem. Soc. Dalt Trans. 1984; 0: 615-620.
  • 20. Flower, K. R., Alder, M.J., Cross, W. I., Pritchard, R. G., Azo-phosphine containing complexes of Group 6 metal carbonyls: crystal and molecular structure of [Mo(CO)5{1-(4-ethylphenylazo)-6-diphenylphosphino-naphthalen-2-ol}]. J. Organomet. Chem., 1998; 568: 279-285.
  • 21. Gavrilov, K. N., Korostylev, A.V., Bondarev, O.G., Lyubimov, S. Y., Kovalevsky, A. Y., Petrovskii, P. V., Davankov, V. A., New palladium(II) complexes of (N,N-dimethylamino)alkoxy-1,3,2-oxazaphospholidine ligands. Inorg.Chim. Acta, 2000; 303: 1-6.
  • 22. Smith, G. S., Mahamo, T., Mogorosi,M. M., Moss, J. R., Mapolie, S. F., Slootweg, J.C., Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts. J. Organomet.Chem. 2012; 703: 34-42.
  • 23. Andjelkovic, K., Radulovic, V., Bacchi, A., Pelizzi, G., Sladic, D., Brceski, I., Synthesis, Structure, and Antimicrobial Activity of Complexes of Pt(II), Pd(II), and Ni(II) with the Condensation Product of 2-(Diphenylphosphino)benzaldehyde and Semioxamazide. Mon. Chem.Chem. Monthly, 2006; 137: 681-691.
  • 24. Smith,G.S., Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C.,Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene. J. Organomet. Chem. 2011; 696: 3585-3592.
  • 25. Keleş¸ M., Yılmaz, M.K., Palladium (II) complexes with aminomethylphosphine ligands as catalysts for the heck reaction. Heteroatom Chem., 2012; 23: 466-471.
  • 26. Serindağ, O., Aydın, Z., Keleş, M., Synthesis of palladium complexes with bis (diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate. J. Organomet. Chem. 2007; 692: 1951-1955.
  • 27. Garrau, P.E., DELTA.R-ring contributions to phosphorus-31 NMR parameters of transition-metal-phosphorus chelate complexes. Chem. Rev. 1981; 81: 229-266.
  • 28. Smith, R.C., Bodner, C. R., Earl, M.J., Sears, N.C., Hill, N. E., Bishop, L.M., Sizemore, N.,Hehemann, D.T., Bohn, J.J., Protasiewiez, J. D., Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines. J. Organomet. Chem. 2005; 690: 477-481. DOI:
  • 29. Pramick, M. R., Rosemeier, S. M., Beranek, M. T., Nickse, S. B., Stone, J. J., Stockland, R.A., Baldwin, Kastner, S.M. M.E., Coupling of Aryl Halides with Aryl Boronic Acids with P (C6H5)(2-C6H4Cl) 2 as the Supporting Ligand. Organomet. 2003; 22: 523-528.
  • 30. Harrington, P.J., Lodewijk, E., Twenty years of naproxen technology. Org. Process Res. Dev. 1997; 1: 72-76.
  • 31. Sabounchei, S. J., Panahimehr, M., Ahmadi, M., Nasri, Z., . Khavasi, H.R., Four-coordinate Pd (II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction. J. Organomet. Chem. 2013; 723: 207-213.
There are 31 citations in total.

Details

Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Mustafa Kemal Yılmaz 0000-0002-9969-3956

Mustafa Keleş 0000-0003-2669-1818

Publication Date September 1, 2017
Submission Date October 3, 2017
Acceptance Date January 2, 2018
Published in Issue Year 2018

Cite

Vancouver Yılmaz MK, Keleş M. The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions. JOTCSA. 2017;5(1):133-48.