EN
The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions
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
Keywords
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.
Details
Primary Language
English
Subjects
Engineering, Chemical Engineering
Journal Section
Research Article
Publication Date
September 1, 2017
Submission Date
October 3, 2017
Acceptance Date
January 2, 2018
Published in Issue
Year 2018 Volume: 5 Number: 1
APA
Yılmaz, M. K., & Keleş, M. (2017). The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions. Journal of the Turkish Chemical Society Section A: Chemistry, 5(1), 133-148. https://doi.org/10.18596/jotcsa.341530
AMA
1.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):133-148. doi:10.18596/jotcsa.341530
Chicago
Yılmaz, Mustafa Kemal, and Mustafa Keleş. 2017. “The Catalytic Activity of Palladium(II) Complexes Containing PN Ligands in the Heck and Suzuki C-C Coupling Reactions”. Journal of the Turkish Chemical Society Section A: Chemistry 5 (1): 133-48. https://doi.org/10.18596/jotcsa.341530.
EndNote
Yılmaz MK, Keleş M (September 1, 2017) The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions. Journal of the Turkish Chemical Society Section A: Chemistry 5 1 133–148.
IEEE
[1]M. K. Yılmaz and M. Keleş, “The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions”, JOTCSA, vol. 5, no. 1, pp. 133–148, Sept. 2017, doi: 10.18596/jotcsa.341530.
ISNAD
Yılmaz, Mustafa Kemal - Keleş, Mustafa. “The Catalytic Activity of Palladium(II) Complexes Containing PN Ligands in the Heck and Suzuki C-C Coupling Reactions”. Journal of the Turkish Chemical Society Section A: Chemistry 5/1 (September 1, 2017): 133-148. https://doi.org/10.18596/jotcsa.341530.
JAMA
1.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;5:133–148.
MLA
Yılmaz, Mustafa Kemal, and Mustafa Keleş. “The Catalytic Activity of Palladium(II) Complexes Containing PN Ligands in the Heck and Suzuki C-C Coupling Reactions”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 5, no. 1, Sept. 2017, pp. 133-48, doi:10.18596/jotcsa.341530.
Vancouver
1.Mustafa Kemal Yılmaz, Mustafa Keleş. The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions. JOTCSA. 2017 Sep. 1;5(1):133-48. doi:10.18596/jotcsa.341530
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