N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION

Volume: 3 Number: 3 January 8, 2017
  • Rukiye Fırıncı
EN

N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION

Abstract

A series of N-butyl substituted imidazolium salts, (1a-c) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes (2a-c) were synthesized and characterized. Pd-NHC complexes were fully determined by elemental analysis and spectroscopic. The synthesized complexes were tested in Suzuki-Miyaura cross-coupling reaction. These complexes were found to be efficient catalysts for the Suzuki-Miyaura reaction of phenylboronic acid with aryl bromides.

 

References

  1. Jacobsen H, Correa A, Poater A, Costabile C, Cavallo L. Understanding the M(NHC) (NHC=N-heterocyclic carbene) bond. Coordination Chemistry Reviews. 2009 Mar;253:687-703. DOI: 10.1016/j.ccr.2008.06.006.
  2. Boehme C, Frenking G. Electronic structure of stable carbenes, silylenes, and germylenes. Journal of the American Chemical Society. 1996 Feb;118:2039-46. DOI: 10.1021/ja9527075.
  3. Viciu M. S, Navarro O, Germaneau R. F, Kelly R. A, Sommer W, Marion N, Stevens E. D, Cavallo L, Nolan S. P. Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene). Organometallics. 2004 Feb;23:1629-35. DOI: 10.1021/om034319e.
  4. a. Diez C, Nagel U. Chiral iridium(I) bis(NHC) complexes as catalysts for asymmetric transfer hydrogenation. Applied Organometallic Chemistry. 2010 Apr;24:509-516. DOI: 10.1002/aoc.1650. b. Crudden C. M, Allen D. P. Stability and reactivity of N-heterocyclic carbene complexes. Coordination Chemistry Reviews. 2004 Dec;248:2247-73. DOI: 10.1016/j.ccr.2004.05.013. c. Crabtree R. H. NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis. Journal of Organometallic Chemistry. 2005 Dec;690:5451-57. DOI: 10.1016/j.jorganchem.2005.07.099.
  5. Herrmann W. A. N-Heterocyclic Carbenes: A new concept in organometallic catalysis. Angewandte Chemie International Edition. 2002 Apr;41:1290-1309. DOI: 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y.
  6. Hahn F. E. Heterocyclic carbenes. Angewandte Chemie International Edition. 2006 Jan;45:1348-52. DOI: 10.1002/anie.200503858.
  7. ArduengoIII A. J, Harlow R. L, Kline M. A stable crystalline carbene. Journal of the American Chemical Society. 1991 Jan;113:361-63. DOI: 10.1021/ja00001a054.
  8. Mangalum A, McMillen C. D, Tennyson A. G. Synthesis, coordination chemistry and reactivity of transition metal complexes supported by a chelating benzimidazolylidene carboxylate ligand. Inorganica Chimica Acta. 2015 Feb;426:29-38. DOI: 10.1016/j.ica.2014.11.003.

Details

Primary Language

English

Subjects

-

Journal Section

-

Authors

Rukiye Fırıncı This is me

Publication Date

January 8, 2017

Submission Date

July 1, 2016

Acceptance Date

-

Published in Issue

Year 2016 Volume: 3 Number: 3

APA
Fırıncı, R. (2017). N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. Journal of the Turkish Chemical Society Section A: Chemistry, 3(3), 93-104. https://doi.org/10.18596/jotcsa.90024
AMA
1.Fırıncı R. N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. JOTCSA. 2017;3(3):93-104. doi:10.18596/jotcsa.90024
Chicago
Fırıncı, Rukiye. 2017. “N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION”. Journal of the Turkish Chemical Society Section A: Chemistry 3 (3): 93-104. https://doi.org/10.18596/jotcsa.90024.
EndNote
Fırıncı R (January 1, 2017) N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. Journal of the Turkish Chemical Society Section A: Chemistry 3 3 93–104.
IEEE
[1]R. Fırıncı, “N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION”, JOTCSA, vol. 3, no. 3, pp. 93–104, Jan. 2017, doi: 10.18596/jotcsa.90024.
ISNAD
Fırıncı, Rukiye. “N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION”. Journal of the Turkish Chemical Society Section A: Chemistry 3/3 (January 1, 2017): 93-104. https://doi.org/10.18596/jotcsa.90024.
JAMA
1.Fırıncı R. N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. JOTCSA. 2017;3:93–104.
MLA
Fırıncı, Rukiye. “N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 3, no. 3, Jan. 2017, pp. 93-104, doi:10.18596/jotcsa.90024.
Vancouver
1.Rukiye Fırıncı. N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. JOTCSA. 2017 Jan. 1;3(3):93-104. doi:10.18596/jotcsa.90024

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