European Journal of Chemistry 2019, 10(4), 367-375 | doi: https://doi.org/10.5155/eurjchem.10.4.367-375.1915 | Get rights and content

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Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water


Othman Abduallah Al-Fulaij (1) orcid , Abdel-Zaher Abdelaziz Elassar (2,*) orcid , Kamal Mohamed Dawood (3) orcid

(1) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(2) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(3) Chemistry Department, Faculty of Science, Kuwait University, Safat-13060, Kuwait
(*) Corresponding Author

Received: 07 Jul 2019 | Revised: 20 Sep 2019 | Accepted: 27 Sep 2019 | Published: 31 Dec 2019 | Issue Date: December 2019

Abstract


The 1,3-dipolar cycloaddition reaction of bis-hydrazonyl chlorides with methyl propiolate afforded dimethyl 1,1¢-aryl-3,3`-bipyrazole-4,4`-dicarboxylates (5a,b). Heating the later compound 5a with a mixture of HCl/AcOH gave 3,3`-bipyrazole-5,5`-dicarboxylic acid derivative 6. Treatment of the hydrazonoyl chloride (1a) and 3,3`-bipyrazole-5,5`-dicarboxylic acid (6) with palladium(II) chloride gave the corresponding Pd-complexes 7 and 8, respectively. The catalytic activity of the prepared Pd-complexes was examined in the Suzuki cross-coupling reaction of phenylboronic acid with activated and deactivated aryl(hetaryl) bromides. The catalyst system provides very good to excellent yields, 85-94%. The structures of the obtained products were established from their elemental analysis, spectral data, XPS, EDX, and single crystal X-ray crystallography. Crystal data for C10H7N2O2 (6): triclinic, space group P-1 (no. 2), a = 3.9956(10) Å, b = 9.8917(18) Å, c = 10.810(3) Å, α = 94.167(15)°, β = 94.979(19)°, γ = 98.953(15)°, V = 418.83(16) Å3, Z = 2, T = 296.(2) K, μ(Cu Kα) = 0.887 mm-1, Dcalc = 1.484 g/cm3, 5469 reflections measured (11.72° ≤ 2Θ ≤ 133.24°), 1420 unique (Rint = 0.0633, Rsigma = 7.24%) which were used in all calculations. The final R1 was 0.1055 (>2sigma(I)) and wR2 was 0.3620 (all data).


Keywords


Bipyrazoles; C-C coupling; Heterocycles; Pd-complexes; X-ray single crystal; Bis-hydrazonoyl chlorides

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DOI: 10.5155/eurjchem.10.4.367-375.1915

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Funding information


This research work is funded by Kuwait University, research project grant SC-13/15.

Citations

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[1]. Mohammad Suhail, Sofi Danish Mukhtar, Imran Ali, Ariba Ansari, Saiyam Arora
Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective
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[2]. Kamal M. Dawood, Ashraf A. Abbas
Synthetic Routes to Bioactive Bipyrazole Derivatives
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DOI: 10.1002/slct.202003436
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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Al-Fulaij, O.; Elassar, A.; Dawood, K. Eur. J. Chem. 2019, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, O.; Elassar, A.; Dawood, K. Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water. Eur. J. Chem. 2019, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, O., Elassar, A., & Dawood, K. (2019). Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water. European Journal of Chemistry, 10(4), 367-375. doi:10.5155/eurjchem.10.4.367-375.1915
Al-Fulaij, Othman, Abdel-Zaher Abdelaziz Elassar, & Kamal Mohamed Dawood. "Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water." European Journal of Chemistry [Online], 10.4 (2019): 367-375. Web. 29 Nov. 2021
Al-Fulaij, Othman, Elassar, Abdel-Zaher, AND Dawood, Kamal. "Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water" European Journal of Chemistry [Online], Volume 10 Number 4 (31 December 2019)

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