Pyrazole-directed, fluoroalcohol-free arylation of C-H bonds

Authors

  • Le Van Lam Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT). Vietnam National University Ho Chi Minh City. Author
  • Nguyen Thanh Tung Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT), Vietnam. Vietnam National University Ho Chi Minh City, Vietnam. Author

DOI:

https://doi.org/10.62239/jca.2024.001

Keywords:

arylation, palladium, functionalization

Abstract

Directed arylation of sp2 C−H bonds is often considered one of the most convenient methods to rapidly increase the complexity of organic molecules. However, most of the available methods utilized fluoroalcohols such as hexafluoroisopropanol (HFIP) as the solvent. Herein we report a simple method for palladium-catalyzed, directed arylation of arene C−H bond using acetic acid solvent. The successful functionalization relies on the use of pyrazole directing group.

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References

P. Gandeepan, T. Müller, D. Zell, G. Cera, S. Warratz, L. Ackermann, Chem. Rev. 119 (2019) 2192-2452. https://doi.org/10.1021/acs.chemrev.8b00507

J. Zhang, X. Lu, C. Shen, L. Xu, L. Ding, G. Zhong, Chem. Soc. Rev. 50 (2021) 3263-3314. https://doi.org/10.1039/D0CS00447B

S. Rej, A. Das, N. Chatani, Coord. Chem. Rev. 431 (2021) 213683. https://doi.org/10.1016/j.ccr.2020.213683

J. Grover, G. Prakash, N. Goswami, D. Maiti, Nat. Commun. 13 (2022) 1085. https://doi.org/10.1021/acs.accounts.1c00168

G. Albano, A. Punzi, M. A. M. Capozzi, G. M. Farinola, Green Chem. 24 (2022) 1809-1894. https://doi.org/10.1039/D1GC03168F

M. Li, J. Wang, Synthesis 54 (2022) 4734-4752. https://doi.org/10.1055/a-1677-5870

R. Giri, N. L. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 129 (2007) 3510-3511. https://doi.org/10.1021/ja0701614

V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 127 (2009) 13154-13155. https://doi.org/10.1021/ja054549f

K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 128 (2006) 14047-14049. https://doi.org/10.1021/ja065718e

J. Jeon, C. Lee, I. Park, S. Hong, Chem. Rec. 21 (2021) 3613-3627. https://doi.org/10.1002/tcr.202100117

G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 52 (2013) 11726-11743. https://doi.org/10.1002/anie.201301451

L. Ackermann, A. Althammer, R. Born, Angew. Chem. Int. Ed. 45 (2006) 2619-2622. https://doi.org/10.1002/anie.200504450

C. J. Teskey, S. M. A. Sohel, D. L. Bunting, S. G. Modha, M. F. Greaney, Angew. Chem. Int. Ed. 56 (2017) 5263-5266. https://doi.org/10.1002/anie.201701523

S. H. Kwak, N. Gulia, O. Daugulis, J. Org. Chem. 82 (2018) 5844-5850. https://doi.org/10.1021/acs.joc.8b00659

N. Gulia, J. Fornalski, A. Gumienna, M. Ambroziak, S. Szafert, Chem. Eur. J. 28 (2022) e202202449. https://doi.org/10.1002/chem.202202449

N. Gulia, O. Daugulis, Angew. Chem. Int. Ed. 56 (2017) 3630-3634. https://doi.org/10.1002/anie.201611407

T. Bhattacharya, A. Ghosh, D. Maiti, Chem. Sci. 12 (2021) 3857-3870. https://doi.org/10.1039/D0SC06937J

H. F. Motiwala, A. M. Armaly, J. G. Cacioppo, T. C. Coombs, K. R. K. Koehn, V. M. Norwood, IV, J. Aubé, Chem. Rev. 122 (2022) 12544-12747. https://doi.org/10.1021/acs.chemrev.1c00749

Published

09-03-2024

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How to Cite

Pyrazole-directed, fluoroalcohol-free arylation of C-H bonds. (2024). Vietnam Journal of Catalysis and Adsorption, 13(1), 01-04. https://doi.org/10.62239/jca.2024.001

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