TR
EN
N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction
Abstract
N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes (Cat-1-5) were used for the first time as catalysts in the Suzuki-Miyaura reaction between aryl bromides and arylboronic acids. All complexes screened were found to be excellent catalysts in the selected coupling between 4-bromobenzaldehyde and phenylboronic acid at room temperature. Cat-3 was shown to be the most efficient one and used for the optimisation of the reaction conditions and determining the substrate scope. The application of the optimised method provided a series of biaryls (3a-l) in excellent isolated yields. With these promising results the catalysts could be applied succesfully to some other classic cross-coupling reactions such as Sonogashira, Stille and Buchwald-Hartwig.
Keywords
Thanks
Prof. Dr. Nejdet Coşkun
References
- [1] Blakemore D.C., Suzuki-Miyaura Coupling. In: Blakemore D.C., Doyle P.M., Fobian Y.M., (Eds). Synthetic Methods in Drug Discovery Volume 1. Cambridge: RSC, (2016); 1-69.
- [2] Koshvandi T. K. A., Heravi M. M., Momeni T., Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update, Appl. Organomet. Chem., 32(3) (2018) 1–59.
- [3] Dhangar G., Serrano J. L., Schulzke C., Gunturu K. C., Kapdi A. R., Palladacycle-Catalyzed Triple Suzuki Coupling Strategy for the Synthesis of Anthracene-Based OLED Emitters, ACS Omega, 2(7) (2017) 3144–3156.
- [4] García-López J. A., Greaney M. F., Synthesis of biaryls using aryne intermediates, Chem. Soc. Rev., 45(24) (2016) 6766–6798.
- [5] Beletskaya I. P., Alonso F., Tyurin V., The Suzuki-Miyaura reaction after the Nobel prize, Coord. Chem. Rev., 385(2019) 137–173.
- [6] Hooshmand S. E., Heidari B., Sedghi R., Varma R. S., Recent advances in the Suzuki-Miyaura cross-coupling reaction using efficient catalysts in eco-friendly media, Green Chem., 21(3) (2019) 381–405.
- [7] Froese R. D. J., Lombardi C., Pompeo M., Rucker R. P., Organ M. G., Designing Pd-N-Heterocyclic Carbene Complexes for High Reactivity and Selectivity for Cross-Coupling Applications, Acc. Chem. Res., 50(9) (2017) 2244–2253.
- [8] Charra V., de Frémont P., Braunstein P., Multidentate N-heterocyclic carbene complexes of the 3d metals: Synthesis, structure, reactivity and catalysis, Coord. Chem. Rev., 341 (2017) 53–176.
Details
Primary Language
English
Subjects
-
Journal Section
Research Article
Authors
Publication Date
March 29, 2021
Submission Date
October 10, 2020
Acceptance Date
January 27, 2021
Published in Issue
Year 2021 Volume: 42 Number: 1
APA
Çetin Korukçu, M. (2021). N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction. Cumhuriyet Science Journal, 42(1), 30-37. https://doi.org/10.17776/csj.808828
AMA
1.Çetin Korukçu M. N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction. CSJ. 2021;42(1):30-37. doi:10.17776/csj.808828
Chicago
Çetin Korukçu, Meliha. 2021. “N-Alkoxycarbonyl Carbamoylmethyl Substituted 1H-Imidazol-2-Yliden-Pd (II) Complexes As Highly Efficient Catalysts for Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal 42 (1): 30-37. https://doi.org/10.17776/csj.808828.
EndNote
Çetin Korukçu M (March 1, 2021) N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction. Cumhuriyet Science Journal 42 1 30–37.
IEEE
[1]M. Çetin Korukçu, “N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction”, CSJ, vol. 42, no. 1, pp. 30–37, Mar. 2021, doi: 10.17776/csj.808828.
ISNAD
Çetin Korukçu, Meliha. “N-Alkoxycarbonyl Carbamoylmethyl Substituted 1H-Imidazol-2-Yliden-Pd (II) Complexes As Highly Efficient Catalysts for Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal 42/1 (March 1, 2021): 30-37. https://doi.org/10.17776/csj.808828.
JAMA
1.Çetin Korukçu M. N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction. CSJ. 2021;42:30–37.
MLA
Çetin Korukçu, Meliha. “N-Alkoxycarbonyl Carbamoylmethyl Substituted 1H-Imidazol-2-Yliden-Pd (II) Complexes As Highly Efficient Catalysts for Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal, vol. 42, no. 1, Mar. 2021, pp. 30-37, doi:10.17776/csj.808828.
Vancouver
1.Meliha Çetin Korukçu. N-Alkoxycarbonyl / carbamoylmethyl substituted 1H-imidazol-2-yliden-Pd (II) complexes as highly efficient catalysts for Suzuki-Miyaura cross-coupling reaction. CSJ. 2021 Mar. 1;42(1):30-7. doi:10.17776/csj.808828
Cited By
The application of Box–Behnken design for the optimization of protocatechuic acid separation by a reactive extractant trioctylphosphine oxide
Biomass Conversion and Biorefinery
https://doi.org/10.1007/s13399-023-03794-w