Synthesis and application of a fluorous Lawesson's reagent: Convenient chromatography-free product purification

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1093-1095

  Kaleta, Zoltán ^a   Tárkányi, Gábor ^a   Gömöry, Ágnes ^a   Kálmán, Ferenc ^b   Nagy, Tamás ^b   Soós, Tibor ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b ComGenex Inc ^*  (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646441438     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0529849     Document Type: Article

References (17)

1. Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: New York, 1996.
2. Perregaard, J.; Scheibye, S.; Meyer, H. J.; Thomsen, I.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1977, 86, 679.
3. Reviews with extensive literature background: (a) Levinson, M. I.; Cava, M. P. Tetrahedron 1985, 41, 5061.
4. (b) Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003, 1929.
5. (a) Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoud, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000; p 25.
6. (b) Gladysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823 and the following articles in this special issue entitled "Fluorous Chemistry".
7. (c) The Handbook on Fluorous Chemistry; Gladysz, J. A., Horváth, I. T., Curran, D. P., Eds.; Wiley-VCH: New York, 2004.
8. Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714.
9. Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.-O. Org. Synth. 1984, 62, 158.
10. For details of the synthesis of the fluorous anisoles 3a-c, see the Supporting Information.
11. Development and application of Wittig methodology in fluorous chemistry: Rocaboy, C.; Rutherford, D.; Bennett, B. L.; Gladysz, J. A. J. Phys. Org. Chem. 2000, 596.
12. Study on the insulation of the electron-withdrawing effect of the perfluoroalkyl groups: Alvey, L. J.; Meier, R.; Soós, T.; Bernatis, P.; Gladysz, J. A. Eur. J. Inorg. Chem. 2000, 1975.
13. For details, see the Supporting Information
14. The primary amides are susceptible to dehydration by Lawesson's reagent: Perregaard, J.; Thomsen, I.; Lawesson, S.-O. Bull. Soc. Chim. Belg. 1977, 87, 321.
15. Some representative microwave applications in Lawesson reactions: (a) Varma, R. S.; Kumar, D. Org. Lett. 1999, 1, 697.
16. (b) Olsson, R.; Hansen, H. C.; Anderson, C.-M. Tetrahedron Lett. 2000, 41, 7947.
17. The mixed sorbent strategy proved to be efficient in fluorous synthesis when polar functionalities are appended several atoms away from the perfluoroalkyl chain: Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319.