Click chemistry approach to ionic liquids (ILs) supported organic synthesis

Authors

  • Alioune fall
  • Insa Seck
  • Massène Sène
  • Mohamed Gaye
  • Matar Seck
  • Generosa Gómez
  • Yagamare Fall

Abstract

A furan substrate anchored to an ionic liquid bound tert-butyldiphenylsiloxane was synthesized using a “click†chemistry approach. The ionic liquid supported furan moiety underwent singlet oxygen oxidation to afford a butenolide intermediate which after removal of the siloxane group gave a bicyclic lactone.

References

- For recent reviews, see (a) T. Welton Chem. Rev. 1999, 99, 2071-2083. (b) P. Wasserscheid, W. Keim Angew. Chem., Int. Ed. 2000, 39, 3772-3789; (c) J. S. Wilkes Green Chem. 2002, 4, 73-80; (d) J. Dupont, R. F. de Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3691; (e) P. Wasserscheid, T. Welton Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany, 2003.

- (a) J-Y. Huang, M. Lei, Y-G. Wang, Tetrahedron Lett. 2006, 47, 3047-3050 and referencies therein. (b) W. Miao, T. H. Chan, Acc. Chem. Res. 2006, 39, 897-908.

- M. M. Meloni, P. D. White, D. Armour, R. C. D. Brown Tetrahedron 2007, 63, 299-311.

- (a) A. Fall, M. Sène, M. Gaye, G. Gómez, Y. Fall, Tetrahedron Lett. 2010, 51, 4501-4504; (b) A. Fall, M. Sène, E. Tojo, G. Gómez, Y. Fall, Synthesis 2010, 20, 3415-3417; (c) A. Fall, M. Sène, O. Diouf, M. Gaye, G. Gómez, Y. Fall, Open Org. Chem.J. 2012, 6, 21-26.

- (a) H. C. Kolb, M. G. Finn, K. B. Sharpless Angew. Chem., Int. Ed. 2001, 40, 2004-2021; (b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem., Int. Ed. 2002, 41, 2596-2599; (c) C. W. Toroe, M. Christensen, M. Meldal J. Org. Chem. 2002, 67, 3057-3064; (d) A. Krasiñski, V. V. Forkin, K. B. Sharpless Org. Lett. 2004, 6, 1237-1240; (e) T. Thirumurugan, D. Matosiuk, K. Jozwiak Chem. Rev. 2013, 113, 4905-4979.

- (a) Y. Fall, B. Vidal, D. Alonso, G. Gómez Tetrahedron Lett. 2003, 44, 4467-4469; (b) M. Pérez, P. Canoa, G. Gómez, C. Terán, Y. Fall Tetrahedron Lett. 2004, 45, 5207-5209; (c) D. Alonso, M. Pérez, G. Gómez, B. Covelo, Y. Fall Tetrahedron. 2005, 61, 2021-2026; (d) M. Teijeira, P. L. Suárez, G. Gómez, C. Terán, Y. Fall Tetrahedron Lett. 2005, 46, 5889-5892; (e) I. García, G. Gómez, M. Teijeira, C. Terán, Y. Fall Tetrahedron Lett. 2006, 47, 1333-1335; (f) P. Canoa, M. Pérez, B. Covelo, G. Gómez, Y. Fall Tetrahedron Lett. 2007, 48, 3441-3443; (g) C. Ãlvarez, M. Pérez, A. Zúñiga, G. Gómez, Y. Fall Synthesis 2010, 22, 3883-3890; (h) P. Canoa, Z. Gándara, M. Pérez, R. Gago, G. Gómez, Y. Fall Synthesis 2011, 3, 431-436; (h) M. Gónzalez, Z. Gándara, B. Covelo, G. Gómez, Y. Fall Tetrahedron Lett. 2011, 52, 5983-5986; (i)A. Zúñiga, G. Pazos, P. Besada, Y. Fall Tetrahedron Lett. 2012, 53, 4293-4295; (j) M. González, Z. Gándara, G. Pazos, G. Gómez, Y. Fall Synthesis 2013, 45, 625-632; (k) M. Gónzalez, Z. Gándara, A. Martínez, G. Gómez, Y. Fall Tetrahedron Lett. 2013, 54, 3647-3650; (l) M. Gónzalez, Z. Gándara, A. Martínez, G. Gómez, Y. Fall Synthesis 2013, 45, 1693-1700; M. González, Z. Gándara, M. Seck, G. Gómez, Y. Fall Mediterr. J. Chem. 2015, 4, 18-29.

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Published

2015-06-26

Issue

Vol. 4 No. 4 (2015)

Section

Organic Chemistry

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