Recent advances on defluorinative carboxylation and decarboxylative fluorination of arenes

Document Type : Review Article

Authors

1 Department of Pharmacy, Al-Zahrawi University College, Karbala, Iraq

2 Department of Medical Laboratory Technics, Al-Noor University College, Nineveh, Iraq

3 Medical Technical College, Al-Farahidi University, Iraq

4 Department of Chemistry, Miandoab Branch, Islamic Azad University, Miandoab, Iran

5 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697 Tehran, Iran

Abstract
Abstract: Compared with most studies in the field of CO2 utilization, which focused on the carboxylation of C-I, C−Br, C−Cl, C−B, C-Si, C-O bonds, the direct defluorinative carboxylation of C−F bonds is more challenging due to the much higher bond dissociation energy and less reactivity of C−F bonds, for which it is difficult to initiate the oxidative addition process under mild conditions. Recently, various catalytic systems have been developed that allow the direct carboxylation of inert C-F bonds with atmospheric CO2 and provide versatile methodologies for green synthesis of carboxylic acid derivatives. This review focuses on recent advances in this challenging and hot research topic with special emphasis on the mechanistic details of the reaction pathways.

Keywords

Subjects


  1. (a) A. Samanta, A. Zhao, G.K. Shimizu, P. Sarkar, R. Gupta, Post-combustion CO2 capture using solid sorbents: a review, Ind. Eng. Chem. Res., 51 (2012) 1438-1463; (b) A.J. Hunt, E.H. Sin, R. Marriott, J.H. Clark, Generation, capture, and utilization of industrial carbon dioxide, ChemSusChem., 3 (2010) 306-322.
  2. Wang, S. Que, Z. Ding, E. Vessally, Oxidative carboxylation of olefins with CO2: environmentally benign access to five-membered cyclic carbonates, RSC Adv., 10 (2020) 10806-10806.
  3. Li, S. Abdolmohammadi, M.S. Hoseininezhad-Namin, F. Behmagham, E. Vessally, Carboxylative cyclization of propargylic alcohols with carbon dioxide: A facile and Green route to α-methylene cyclic carbonates, J. CO2 Util., 38 (2020) 220-231.
  4. (a) W. Xu, D. Guo, A.G. Ebadi, M. Toughani, E. Vessally, Transition-metal catalyzed carboxylation of organoboron compounds with CO2, J. CO2, 45 (2021) 101403; (b) W. Xu, A.G. Ebadi, M. Toughani, E. Vessally, Incorporation of CO2 into organosilicon compounds via C-Si bond cleavage. J. CO2 Util., 43 (2021) 101358; (c) L. Feng, X. Li, B. Liu, E. Vessally, Hydrocarboxylation of alkynes utilizing CO2 as C1 synthon: a facile and environmentally benign access to α, β-unsaturated carboxylic acids, J. CO2 Util., 40 (2020) 101220.
  5. Farshbaf, L.Z. Fekri, M. Nikpassand, R. Mohammadi, E. Vessally, Dehydrative condensation of β-aminoalcohols with CO2: An environmentally benign access to 2-oxazolidinone derivatives, J. CO2 Util., 25 (2018) 194-204.
  6. Hosseinian, S. Farshbaf, R. Mohammadi, A. Monfared, E. Vessally, Advancements in six-membered cyclic carbonate (1, 3-dioxan-2-one) synthesis utilizing carbon dioxide as a C1 source. RSC Adv., 8 (2018) 17976-17988.
  7. Vessally, R. Mohammadi, A. Hosseinian, L. Edjlali, M. Babazadeh, Three component coupling of amines, alkyl halides and carbon dioxide: an environmentally benign access to carbamate esters (urethanes), J. CO2 Util., 24 (2018) 361-368.
  8. Didehban, E. Vessally, M. Salary, L. Edjlali, M. Babazadeh, Synthesis of a variety of key medicinal heterocyclic compounds via chemical fixation of CO2 onto o-alkynylaniline derivatives, J. CO2 Util., 23 (2018) 42-50.
  9. Vessally, A. Hosseinian, L. Edjlali, M. Babazadeh, K. Didehban, Chemical fixation of CO2 to allylic (α-allenylic) amines: A green route to synthesis of functionalized 2-oxazolidones, Mini-Rev. Org. Chem., 15 (2018) 315-323.
  10. Vessally, K. Didehban, M. Babazadeh, A. Hosseinian, L. Edjlali, Chemical fixation of CO2 with aniline derivatives: A new avenue to the synthesis of functionalized azole compounds (A review), J. CO2 Util., 21 (2017) 480-490.
  11. (a) A. Correa, R. Martin, Metal‐catalyzed carboxylation of organometallic reagents with carbon dioxide, Angew. Chem. Int. Ed. Engl., 48 (2009) 6201-6204; (b) W. Zhang, L. Xiaobing, Synthesis of carboxylic acids and derivatives using CO2 as carboxylative reagent, Chinese J. Catal., 33 (2012) 745-756; (c) X.-F. Wu, F. Zheng, Synthesis of carboxylic acids and esters from CO2, Top. Curr. Chem., (2016) 1-60; (d) Y.X. Luan, M. Ye, Transition metal-mediated or catalyzed hydrocarboxylation of olefins with CO2, Tetrahedron Lett., 59 (2018) 853-861; (e) J. Hou, J.S. Li, J. Wu, Recent development of light‐mediated carboxylation using CO2 as the feedstock, Asian J. Org. Chem., 7 (2018) 1439-1447; (f) J. Hong, M. Li, J. Zhang, B. Sun, F. Mo, C-H bond carboxylation with carbon dioxide, ChemSusChem, 12 (2019) 6-39; (g) T. Mita, Y. Sato, Syntheses of α‐Amino Acids by Using CO2 as a C1 Source, Chem. Asian J., 14 (2019) 2038-2047; (h) L. Feng, X. Li, B. Liu, E. Vessally, Hydrocarboxylation of alkynes utilizing CO2 as C1 synthon: A facile and environmentally benign access to α, β-unsaturated carboxylic acids, J. CO2, 40 (2020) 101220.
  12. Wang, Y. Sun, L.Y. Shen, W.C. Yang, F. Meng, P. Li, Photochemical and electrochemical strategies in C–F bond activation and functionalization, Org. Chem. Front., 9 (2022) 853-873.
  13. S. Yan, D.S. Wu, J.H. Ye, L. Gong, X. Zeng, C.K. Ran, Y.Y. Gui, J. Li, D.G. Yu, Copper-catalyzed carboxylation of C–F bonds with CO2, ACS Catal., 9 (2019) 6987-6992.
  14. Y. Bo, S.S. Yan, T.Y. Gao, L. Song, C.K. Ran, Y. He, W. Zhang, G.M. Cao, D.G. Yu, Visible-light photoredox-catalyzed selective carboxylation of C(sp2)−F bonds in polyfluoroarenes with CO2, Chinese J. Catal., 43 (2022) 2388-2394.
  15. Zhu, Y.F. Zhang, Z.Y. Liu, L. Zhou, H. Liu, C. Feng, Selective C–F bond carboxylation of gem-difluoroalkenes with CO2 by photoredox/palladium dual catalysis, Chem. Sci., 10 (2019) 6721-6726.
  16. L. Xie, X.T. Gao, H.H. Wu, F. Zhou, J. Zhou, Direct electrochemical defluorinative carboxylation of gem-difluoroalkenes with carbon dioxide, Org. Lett., 22 (2020) 8424-8429.
  17. T. Gao, Z. Zhang, X. Wang, J.S. Tian, S.L. Xie, F. Zhou, J. Zhou, Direct electrochemical defluorinative carboxylation of α-CF3 alkenes with carbon dioxide, Chem. Sci., 11 (2020) 10414-10420.
  18. Senboku, K. Yoneda, S. Hara, Regioselective electrochemical carboxylation of polyfluoroarenes, Electrochem., 81 (2013) 380-382.
  19. Fujii, K. Semba, Q.Z. Li, S. Sakaki, Y. Nakao, Magnesiation of aryl fluorides catalyzed by a rhodium–aluminum complex, J. Am. Chem. Soc., 142 (2020) 11647-11652.
  20. Pei, B. Wang, Nickel‐catalyzed carboxylation of aryl C−F bonds with CO2, Adv. Synth. Catal., 364 (2022)1245-1250.
  21. Y. Bo, S.S. Yan, T.Y. Gao, L. Song, C.K. Ran, Y. He, W. Zhang, G.M. Cao, D.G. Yu, Visible-light photoredox-catalyzed selective carboxylation of C(sp2)−F bonds in polyfluoroarenes with CO2, Chinese Journal of Catalysis, 43 (2022) 2388-2394.
Volume 6, Issue 3 - Serial Number 3
Autumn 2023
Pages 235-244

  • Receive Date 08 August 2023
  • Revise Date 06 September 2023
  • Accept Date 14 October 2023