Research Article

A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions

Volume: 17 Number: 4 December 29, 2021
EN

A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions

Abstract

1-(2,5-dimethylbenzyl)benzimidazole (1) and 1,3-bis(2,5-dimethylbenzyl)benzimidazolium chloride (2) were prepared. The reaction of 2 with Pd(OAc)2, LiCl and Et3N gave [PdCl2{1,3-bis(2,5-dimethylbenzyl)benzimidazolin-2-ylidene}(PPh3)] (3) complex. The prepared compounds were characterized by NMR, FT-IR, elemental analysis and also LC-MSMS (for 3). The palladium complex 3 was used as catalyst in Suzuki –Miyaura cross-coupling reactions of some aryl bromides and chlorides with phenylboronic acid.

Keywords

References

  1. 1. Miyaura, N, Yamada, K, Suzuki, A. 1979. A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides. Tetrahedron Letters; 20(36): 3437-3440.
  2. 2. Miyaura, N, Suzuki, A. 1979. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. Journal of the Chemical Society, Chemical Communications; 19: 866-867.
  3. 3. Pagett, AB, Lloyd-Jones, GC. Suzuki–Miyaura cross-coupling. In: Denmark SE et al. (ed.) Organic Reactions, Wiley, UK, 2019, pp 547-620.
  4. 4. Talukder, MM, Cue, JMO, Miller, JT, Gamage, PL, Aslam, A, McCandless, GT, Biewer, MC, Stefan, MC. 2020. Ligand steric effects of α-diimine nickel(II) and palladium(II) complexes in the Suzuki–Miyaura cross-coupling reaction. ACS Omega; 5(37): 24018-24032.
  5. 5. D’Accriscio, F, Ohleier, A, Nicolas, E, Demange, M, Boullay, OTD, Saffon-Merceron, N, Fustier-Boutignon, M, Rezabal, E, Frison, G, Nebra, N, Mezailles, N. 2020. [(dcpp)Ni(η2-Arene)] precursors: Synthesis, reactivity, and catalytic application to the Suzuki–Miyaura reaction. Organometallics; 39(10): 1688-1699.
  6. 6. Ansari, RM, Kumar, LM, Bhat, BR. 2018. Air-stable cobalt(II) and nickel(II) Complexes with schiff base Ligand for catalyzing Suzuki–Miyaura cross-coupling reaction. Russian Journal of Coordination Chemistry; 44: 1-8.
  7. 7. Key, RJ, Tengco, JMM, Smith, MD, Vannucci, AK. 2019. A molecular/heterogeneous nickel catalyst for Suzuki–Miyaura coupling. Organometallics; 38(9): 2007-2014.
  8. 8. Ansari, RM, Bhat, BR. 2017. Schiff base transition metal complexes for Suzuki–Miyaura cross-coupling reaction. Journal of Chemical Sciences; 129: 1483-1490.

Details

Primary Language

English

Subjects

Engineering

Journal Section

Research Article

Publication Date

December 29, 2021

Submission Date

May 24, 2021

Acceptance Date

November 23, 2021

Published in Issue

Year 2021 Volume: 17 Number: 4

APA
Demir Atlı, D. (2021). A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions. Celal Bayar University Journal of Science, 17(4), 405-415. https://doi.org/10.18466/cbayarfbe.941916
AMA
1.Demir Atlı D. A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions. CBUJOS. 2021;17(4):405-415. doi:10.18466/cbayarfbe.941916
Chicago
Demir Atlı, Deniz. 2021. “A Mixed N-Heterocyclic Carbene Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions”. Celal Bayar University Journal of Science 17 (4): 405-15. https://doi.org/10.18466/cbayarfbe.941916.
EndNote
Demir Atlı D (December 1, 2021) A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions. Celal Bayar University Journal of Science 17 4 405–415.
IEEE
[1]D. Demir Atlı, “A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions”, CBUJOS, vol. 17, no. 4, pp. 405–415, Dec. 2021, doi: 10.18466/cbayarfbe.941916.
ISNAD
Demir Atlı, Deniz. “A Mixed N-Heterocyclic Carbene Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions”. Celal Bayar University Journal of Science 17/4 (December 1, 2021): 405-415. https://doi.org/10.18466/cbayarfbe.941916.
JAMA
1.Demir Atlı D. A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions. CBUJOS. 2021;17:405–415.
MLA
Demir Atlı, Deniz. “A Mixed N-Heterocyclic Carbene Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions”. Celal Bayar University Journal of Science, vol. 17, no. 4, Dec. 2021, pp. 405-1, doi:10.18466/cbayarfbe.941916.
Vancouver
1.Deniz Demir Atlı. A Mixed N-Heterocyclic Carbene/Triphenylphosphine Palladium(II) Complex for Suzuki-Miyaura Cross-Coupling Reactions. CBUJOS. 2021 Dec. 1;17(4):405-1. doi:10.18466/cbayarfbe.941916