Synthesis 2017; 49(05): 973-980
DOI: 10.1055/s-0036-1588088
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Applications of Solid-Supported Ammonium Fluorides in Organic Synthesis

Daniela Lanari
a   Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy
,
Oriana Piermatti
b   Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy   Email: luigi.vaccaro@unipg.it
,
Chiara Morozzi
a   Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo 1, 06123 Perugia, Italy
,
Stefano Santoro
b   Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy   Email: luigi.vaccaro@unipg.it
,
Luigi Vaccaro*
b   Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy   Email: luigi.vaccaro@unipg.it
› Author Affiliations
Further Information

Publication History

Received: 21 August 2016

Accepted after revision: 07 October 2016

Publication Date:
10 November 2016 (online)


Abstract

This review summarizes recent contributions on the use of fluoride catalysts immobilized on polymer supports. Besides the commercially available Amberlyst fluoride, TBAF on silica gel, and TBAF on alumina, that have proved widely useful for several interesting and valuable synthetic C–N, C–O, and C–C bond transformations, novel catalysts based on the DABCO moiety have allowed access to very useful, new transformations.

1 Introduction

2 Polystyryl-DABCOF2

3 Polystyryl-DABCOF

4 Amberlyst Fluoride (Amb-F)

5 TBAF on Alumina or on Silica Gel

6 Conclusion

 
  • References

    • 1a Clark JH. Chem. Rev. 1980; 80: 429
    • 1b Wilkinson JA. Chem. Rev. 1992; 92: 505
    • 1c Sheppard WA, Sharts CM. Organic Fluorine Chemistry . W. A. Benjamin; New York: 1969
    • 2a Corey EJ, Venkateswarlu A. J. Am. Chem. Soc. 1972; 94: 6190
    • 2b Kremsky JN, Sinha ND. Bioorg. Med. Chem. Lett. 1994; 4: 2171
    • 2c Amantini D, Belleggia R, Fringuelli F, Pizzo F, Vaccaro L. J. Org. Chem. 2004; 69: 2896
    • 2d Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L. J. Org. Chem. 2005; 70: 6526
    • 2e D’Ambrosio G, Fringuelli F, Pizzo F, Vaccaro L. Green Chem. 2005; 7: 874
    • 3a Ismalaj E, Strappaveccia G, Ballerini E, Elisei F, Piermatti O, Gelman D, Vaccaro L. ACS Sustainable Chem. Eng. 2014; 2: 2461
    • 3b Hiyama T. Organofluorine Compounds: Chemistry and Applications. Springer-Verlag; New York: 2000
    • 3c Bhadury PS, Raza SK, Jaiswal DK. J. Fluorine Chem. 1999; 99: 115
    • 3d Mann J. Chem. Soc. Rev. 1987; 16: 381
    • 3e Sharts CM, Sheppard WA. Org. React. 1974; 21: 125
    • 4a Clacens J.-M, Genuit D, Delmotte L, Garcia-Ruiz A, Bergeret G, Montiel R, Lopez J, Figueras F. J. Catal. 2004; 221: 483
    • 4b Blass BE. Tetrahedron 2002; 58: 9301
    • 4c Clark JH, Macquarrie DJ. J. Org. Process Res. Dev. 1997; 1: 149
    • 4d Yoshiharu N, Seiji N, Shigetoshi K, Hiroshi M, Minoru I. Bull. Chem. Soc. Jpn. 1992; 65: 2934
    • 4e Ueki M, Amemiya M. Tetrahedron Lett. 1987; 28: 6617
    • 4f Bergbreiter DE, Lalonde JJ. J. Org. Chem. 1987; 52: 1601
    • 4g Clark JH, Cork DG, Robertson MS. Chem. Lett. 1983; 1145
    • 4h Clark JH, Cork DG, Gibbs HW. J. Chem. Soc., Perkin Trans. 1 1983; 2253
    • 5a Porta R, Benaglia M, Puglisi A. Org. Process Res. Dev. 2016; 20: 2
    • 5b Chiroli V, Benaglia M, Puglisi A, Porta R, Jumde RP, Mandoli A. Green Chem. 2014; 16: 2798
    • 5c Catalytic Methods in Asymmetric Synthesis: Advanced Materials, Techniques, and Applications. Gruttadauria M, Giacalone F. Wiley; Hoboken: 2011
    • 5d Recoverable and Recyclable Catalysts . Benaglia M. Wiley; Chichester: 2009
    • 5e Benaglia M, Puglisi A, Cozzi F. Chem. Rev. 2003; 103: 3401
    • 5f McNamara CA, Dixon MJ, Bradley M. Chem. Rev. 2002; 102: 3275
    • 5g Ley SV, Baxendale IR, Bream RN, Jackson PS, Leach AG, Longbottom DA, Nesi M, Scott JS, Storer RI, Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000; 3815
  • 6 Fringuelli F, Lanari D, Pizzo F, Vaccaro L. Curr. Org. Synth. 2009; 6: 203
  • 7 Lenardão EJ, Soares LK, Barcellos AM, Perin G. Curr. Green Chem. 2016; 3: 4
  • 8 Angelini T, Lanari D, Maggi R, Pizzo F, Sartori G, Vaccaro L. Adv. Synth. Catal. 2012; 354: 908
  • 9 Ballerini E, Crotti P, Frau I, Lanari D, Pizzo F, Vaccaro L. Green Chem. 2013; 15: 2394
    • 10a Ballerini E, Curini M, Gelman D, Lanari D, Piermatti O, Pizzo F, Santoro S, Vaccaro L. ACS Sustainable Chem. Eng. 2015; 3: 1221
    • 10b Angelini T, Bonollo S, Lanari D, Pizzo F, Vaccaro L. Org. Lett. 2012; 14: 4610
  • 11 Angelini T, Bonollo S, Ballerini E, Lanari D, Maggi R, Piermatti O, Sartori G, Vaccaro L. J. Flow Chem. 2014; 4: 40
  • 12 Andraos J, Ballerini E, Vaccaro L. Green Chem. 2015; 17: 913
  • 13 Ballerini E, Maggi G, Pizzo F, Piermatti O, Gelman D, Vaccaro L. Org. Process Res. Dev. 2016; 20: 474
  • 14 Fringuelli F, Lanari D, Pizzo F, Vaccaro L. Green Chem. 2010; 12: 1301
  • 15 Strappaveccia G, Angelini T, Bianchi L, Santoro S, Piermatti O, Lanari D, Vaccaro L. Adv. Synth. Catal. 2016; 358: 2134
  • 16 Strappaveccia G, Lanari D, Gelman D, Pizzo F, Rosati O, Curini M, Vaccaro L. Green Chem. 2013; 15: 199
  • 17 Lanari D, Alonzi M, Ferlin F, Santoro S, Vaccaro L. Org. Lett. 2016; 18: 2680
    • 18a Kiefel MJ In Comprehensive Organic Functional Group Transformations II . Vol. 3. Katritzky AR, Taylor RJ. K. Elsevier; Oxford: 2005: 657-684

    • For selected recent examples, see:
    • 18b Powell KJ, Han L.-C, Sharma P, Moses JE. Org. Lett. 2014; 16: 2158
    • 18c Yin W, Wang C, Huang Y. Org. Lett. 2013; 15: 1850
    • 18d Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2011; 50: 519
    • 18e Qin C, Jiao N. J. Am. Chem. Soc. 2010; 132: 15893
  • 19 Marciano D, Goldvaser M, Columbus I, Zafrani Y. J. Org. Chem. 2011; 76: 8549
  • 20 Chan JM. W, Sardon H, Engler AC, García JM, Hedrick JL. ACS Macro Lett. 2013; 2: 860
  • 21 Wang J.-Q, Kong D.-L, Chen J.-Y, Cai F, He L.-N. J. Mol. Catal. A: Chem. 2006; 249: 143
  • 22 Lanari D, Ballini R, Palmieri A, Pizzo F, Vaccaro L. Eur. J. Org. Chem. 2011; 2874