대한방사성의약품학회지 (Journal of Radiopharmaceuticals and Molecular Probes)

  • 제7권2호
  • /
  • Pages.141-146
  • /
  • 2021
  • /
  • 2384-1583(pISSN)
  • /
  • 2508-3848(eISSN)
대한방사성의약품학회 (Korean Society of Radiopharmaceuticals and Molecular Probes)
권호 표지
DOI QR코드

DOI QR Code

Calix-Arene based phase transfer catalysts fornucleophilic fluorination

  • Minji Nam (Department of Chemistry and Chemical Engineering, Inha University) ;
  • Dong Wook Kim (Department of Chemistry and Chemical Engineering, Inha University)
  • 투고 : 2021.06.07
  • 심사 : 2021.06.28
  • 발행 : 2021.12.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

With increasing interest in fluorinated compounds, nucleophilic fluorination reaction has been generally used for synthesizing fluorine-containing chemicals. However, alkali metal fluorides (MFs) generally have low solubility and reactivity in organic solvent. To overcome these problems, various phase transfer catalysts (PTCs) have been investigated. Calix-arene is known as to capture the metal cation(M+), and therefore in this review, we would like to introduce several kinds of calix-arene based PTCs, such as bis-tert-alcohol-functionalized crown-6-calix[4]arene (BACCA), oligo-ethylene glycol linked bis-triethyleneglycol crown-5-calix[4]arene (BTC5A), and ionic liquid functionalized calix-arene based catalyst, as well as ion-pair receptor crown-6-calix[4]arene-capped calix[4]pyrrole.

키워드

과제정보

This work was supported by the Basic Science Research Program (grant code:NRF20201AC1009017), administered through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT, and Future Planning, KOREA.

참고문헌

  1. Lee JW, Oliveira MT, Jang HB, Lee S, Chi DY, Kim DW, Song CE. Hydrogen-bond promoted nucleophilic fluorination: concept, mechanism and applications in positron emission tomography. Chem Soc Rev 2016;45:4638-4650. https://doi.org/10.1039/C6CS00286B
  2. Campbell MG, Ritter T. Modern carbon-fluorine bond forming reactions for aryl fluoride synthesis. Chem Rev 2015;115:612-633. https://doi.org/10.1021/cr500366b
  3. Jadhav VH, Jang SH, Jeong HJ, Lim ST, Sohn MH, Chi DY, Kim DW. Polymer-supported pentaethylene glycol as a facile heterogeneous catalyst for nucleophilic fluorination. Org Lett 2010;12:3740-3743. https://doi.org/10.1021/ol101485n
  4. Kim DW, Jeong HJ, Lim ST, Sohn MH. Tetrabutylammonium tetra(tert-butyl alcohol)-coordinated fluoride as a facile fluoride source. Angew Chem 2008;120:8532-8534. https://doi.org/10.1002/ange.200803150
  5. Carvalho NF, Pliego JR. Theoretical design and calculation of a crown ether phase-transfer-catalyst scaffold for nucleophilic fluorination merging two catalytic concepts. J Org Chem 2016;81:8455-8463. https://doi.org/10.1021/acs.joc.6b01624
  6. Kim DW, Chi DY. Polymer-supported ionic liquids: imidazolium salts as catalysts for nucleophilic substitution reactions including fluorinations. Angew Chem Int Ed 2004;43:483-485. https://doi.org/10.1002/anie.200352760
  7. Pilcher AS, Ammon HL, DeShong P. Utilization of tetrabutylammonium triphenylsilyldifluoride as a fluoride source for nucleophilic fluorination. J Am Chem Soc 1995;117:5166-5167. https://doi.org/10.1021/ja00123a025
  8. Km DW, Song CE, Chi DY. New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity. J Am Chem Soc 2002;124:10278-10279. https://doi.org/10.1021/ja026242b
  9. Jadhav VH, Kim JG, Park SH, Kim DW. Task-specific hexaethylene glycol bridged di-cationic ionic liquids as catalysts for nucleophilic fluorination using potassium fluoride. Chem Eng J 2017;308:664-668. https://doi.org/10.1016/j.cej.2016.09.118
  10. Kim DW, Hong DJ, Jang KS, Chi DY. Structural modification of polymer-supported ionic liquids as catalysts for nucleophilic substitution reactions including fluorination. Adv Synth Catal 2006;348:1719-1727. https://doi.org/10.1002/adsc.200606119
  11. Joseph R, Rao CP. Ion and molecular recognition by lower rim 1,3-di-conjugates of calix[4]arene as receptors. Chem Rev 2011;111:4658-4702. https://doi.org/10.1021/cr1004524
  12. Bohmer V. Calixarenes, macrocycles with (almost) unlimited possibilities. Angew Chem Int Ed Engl 1995;34:713-745. https://doi.org/10.1002/anie.199507131
  13. Scheerder J, Duynhoven JPM, Engbersen JFJ, Reinhoudt DN. Solubilization of NaX salts in chloroform by bifunctional receptors. Angew Chem Int Ed Engl 1996;35:1090-1093. https://doi.org/10.1002/anie.199610901
  14. Sisson AL, Shah MR, Bhosale S, Matile S. Synthetic ion channels and pores(2004-2005). Chem Soc Rev 2006;35:1269-1286. https://doi.org/10.1039/B512423A
  15. Sessler JL, Kim SK, Gross DE, Lee CH, Kim JS, Lynch VM. Crown-6-calix[4]arene-capped calix[4]pyrrole: an ion-pair receptor for solvent-separated CsF ions. J Am Chem Soc 2008;130:13162-13166. https://doi.org/10.1021/ja804976f
  16. Sessler JL, Gross DE, Cho WS, Lynch VM, Schmidtchen FP, Bates GW, Light ME, Gale PA. Calix[4]pyrrole as a chloride anion receptor: solvent and counteraction effects. J Am Chem Soc 2006;128:12281-12288. https://doi.org/10.1021/ja064012h
  17. Casnati A, Barboso S, Rouquette H, Schwing-Weill M-J, Arnaud-Neu F, Dozol J-F, Ungaro R. New efficient calixarene amide ionophores for the selective removal of strontium ion from nuclear waste: synthesis, complexation, and extraction properties. J Am Chem Soc 2001;123:12182-12190. https://doi.org/10.1021/ja016597f
  18. Dondoni A, Marra A. Calixarene and calixresorcarene glycosides: their synthesis and biological applications. Chem Rev 2010;110:4949-4977. https://doi.org/10.1021/cr100027b
  19. Sameni S, Jeunesse C, Matt D, Harrowfield J. Calix[4]arene daisychains. Chem Soc Rev 2009;38:2117-2146. https://doi.org/10.1039/b900183b
  20. Kim DW, Ahn D-S, Oh Y-H, Lee S, Kil HS, Oh SJ, Lee SJ, Kim JS, Ryu JS, Moon DH, Chi DY. A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules. J Am Chem Soc 2006;128:16394-16397. https://doi.org/10.1021/ja0646895
  21. Jadhav VH, Choi W, Lee S-S, Lee S, Kim DW. Bis-tert-alcohol-functionalized crown-6-calix[4]arene: an organic promoter for nucleophilic fluorination. Chem Eur J 2016;22:4515-4520. https://doi.org/10.1002/chem.201504602
  22. O'Hagan D, Deng H. Enzymatic fluorination and biotechnological developments of the fluorinase. Chem Rev 2015;115:634-649. https://doi.org/10.1021/cr500209t
  23. Han HJ, Lee S-S, Kang SM, Kim Y, Park C, Yoo S, Kim CH, Oh Y-H, Lee S, Kim DW. The effects of structural modifications of bis-tert-alcohol-functionalized crown-calix[4]arenes as nucleophilic fluorination promotors and relations with computational predictions. Eur J Org Chem 2020;2020:728-735. https://doi.org/10.1002/ejoc.201901746
  24. Engle KM, Pfeifer L, Pidgeon GW, Giuffredi GT, Thompson AL, Paton RS, Brown JM, Gouverneur V. Coordination diversity in hydrogen-bonded homoleptic fluoride-alcohol complexes modulates reactivity. Chem Sci 2015;6:5293-5302. https://doi.org/10.1039/C5SC01812A
  25. Zechel DL, Reid SP, Nashiru O, Mayer C, Stoll D, Jakeman DL, Warren AJ, Withers SG. Enzymatic synthesis of carbon-fluorine bonds. J Am Chem Soc 2001;123:4350-4351. https://doi.org/10.1021/ja005855q
  26. Kang SM, Kim CH, Lee KC, Kim DW. Bis-triethylene glycolic crown-5-calix[4]arene: a promoter of nucleophilic fluorination using potassium fluoride. Org Lett 2019;21:3062-3066. https://doi.org/10.1021/acs.orglett.9b00649
  27. Greaves TL, Drummond CJ. Protic ionic liquids: properties and applications. Chem Rev 2008;108:206-237. https://doi.org/10.1021/cr068040u
  28. Wasserscheid P, Keim W. Ionic liquids-new "solutions" for transition metal catalysis. Angew Chem Int Ed 2000;39:3772-3789. https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
  29. Yang F, Guo H, Jiao Z, Li C, Ye J. Calixarene ionic liquids: excellent phase transfer catalysts for nucleophilic substitution reaction in water. J Iran Chem Soc 2012;9:327-332 https://doi.org/10.1007/s13738-011-0027-6