Tris(2-(perfluorohexyl)ethyl)tin hydride: A new fluorous reagent for use in traditional organic synthesis and liquid phase combinatorial synthesis

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2531-2532

  Curran, Dennis P ^a   Hadida, Sabine ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYANIDE; KETONE; ORGANIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029914650     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953287m     Document Type: Article

References (28)

1. Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: Chichester, UK. 1992.
2. Zhu, D.-W. Synthesis 1993, 953.
3. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
4. Highlights of the chemistry in refs 3 and 4: (a) Gladysz, J. A. Science 1994, 266, 55. (b) Bergbreiter, D. E. Chemiracts: Org. Chem. 1995, 8, 108.
5. Highlights of the chemistry in refs 3 and 4: (a) Gladysz, J. A. Science 1994, 266, 55. (b) Bergbreiter, D. E. Chemiracts: Org. Chem. 1995, 8, 108.
6. The "ethylene spacer" serves to insulate the phosphorous from the powerful inductive effect of the perfluoroalkyl group.
7. The indicated name is only for convenience. The approved name of 3 is tris(3,3,4.4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)tin hydride.
8. Neumann, W. P. Synthesis 1987, 665.
9. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
10. Compounds 1-3 are new. but a number of compounds related to 1 and 2 are known, see: De Clercq. L.; Willem, R.; Gielen, M.: Atassi. G. Bull. Chem. Soc. Belg. 1984, 93, 1089.
11. 3, 141 mg.
12. BTF: bp 102 °C, d ≈ 1.2, 1 kg = $40 (information taken from the 1995 Aldrich catalog). This has occasionally been used as a solvent, though we are not aware of applications in organic synthesis. Raner, K. D.; Lusztyk, J.: Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 3652. Surya Prakash, G. K. In Synthetic Fluorine Chemistry; Olah, G. A., Chambers, R. D., Surya Prakash, G. K., Eds.: Wiley: New York. 1992; pp 227-57 (see uncited reaction on p 256).
13. BTF: bp 102 °C, d ≈ 1.2, 1 kg = $40 (information taken from the 1995 Aldrich catalog). This has occasionally been used as a solvent, though we are not aware of applications in organic synthesis. Raner, K. D.; Lusztyk, J.: Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 3652. Surya Prakash, G. K. In Synthetic Fluorine Chemistry; Olah, G. A., Chambers, R. D., Surya Prakash, G. K., Eds.: Wiley: New York. 1992; pp 227-57 (see uncited reaction on p 256).
14. Designed after the procedure in the following: Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303.
15. Other alternatives to tributyltin hydride are as follows: Polymeric hydrides: (a) Neumann, W. P.; Peterseim. M. React. Polym. 1993, 20, 189. Acid soluble tin hydrides: (b) Clive, D. L. J.; Yang. W. J. Org. Chem. 1995, 60, 2607. (c) Vedejs. E.; Duncan. S. M.; Haight. A. R. J. Org. Chem. 1993, 58, 3046. Water soluble tin hydrides: (d) Liaht, J.: Brelsow. R. Tetrahedron Lett. 1990, 31, 2957. (e) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
16. Other alternatives to tributyltin hydride are as follows: Polymeric hydrides: (a) Neumann, W. P.; Peterseim. M. React. Polym. 1993, 20, 189. Acid soluble tin hydrides: (b) Clive, D. L. J.; Yang. W. J. Org. Chem. 1995, 60, 2607. (c) Vedejs. E.; Duncan. S. M.; Haight. A. R. J. Org. Chem. 1993, 58, 3046. Water soluble tin hydrides: (d) Liaht, J.: Brelsow. R. Tetrahedron Lett. 1990, 31, 2957. (e) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
17. Other alternatives to tributyltin hydride are as follows: Polymeric hydrides: (a) Neumann, W. P.; Peterseim. M. React. Polym. 1993, 20, 189. Acid soluble tin hydrides: (b) Clive, D. L. J.; Yang. W. J. Org. Chem. 1995, 60, 2607. (c) Vedejs. E.; Duncan. S. M.; Haight. A. R. J. Org. Chem. 1993, 58, 3046. Water soluble tin hydrides: (d) Liaht, J.: Brelsow. R. Tetrahedron Lett. 1990, 31, 2957. (e) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
18. Other alternatives to tributyltin hydride are as follows: Polymeric hydrides: (a) Neumann, W. P.; Peterseim. M. React. Polym. 1993, 20, 189. Acid soluble tin hydrides: (b) Clive, D. L. J.; Yang. W. J. Org. Chem. 1995, 60, 2607. (c) Vedejs. E.; Duncan. S. M.; Haight. A. R. J. Org. Chem. 1993, 58, 3046. Water soluble tin hydrides: (d) Liaht, J.: Brelsow. R. Tetrahedron Lett. 1990, 31, 2957. (e) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
19. Other alternatives to tributyltin hydride are as follows: Polymeric hydrides: (a) Neumann, W. P.; Peterseim. M. React. Polym. 1993, 20, 189. Acid soluble tin hydrides: (b) Clive, D. L. J.; Yang. W. J. Org. Chem. 1995, 60, 2607. (c) Vedejs. E.; Duncan. S. M.; Haight. A. R. J. Org. Chem. 1993, 58, 3046. Water soluble tin hydrides: (d) Liaht, J.: Brelsow. R. Tetrahedron Lett. 1990, 31, 2957. (e) Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221.
20. Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London. 1986.
21. Hadida, S.; Hoshino, M. Unpublished results.
22. Reviews: (a) Terren, N. K.: Gardner, M.: Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. (b) Liskamp, R. M. J. Angew. Chem., Int. Ed. Engt. 1994, 33, 633. (c) Gallop, M. A.: Barrett, R. W.; Dower, W. J.: Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233, 1385.
23. Reviews: (a) Terren, N. K.: Gardner, M.: Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. (b) Liskamp, R. M. J. Angew. Chem., Int. Ed. Engt. 1994, 33, 633. (c) Gallop, M. A.: Barrett, R. W.; Dower, W. J.: Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233, 1385.
24. Reviews: (a) Terren, N. K.: Gardner, M.: Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. (b) Liskamp, R. M. J. Angew. Chem., Int. Ed. Engt. 1994, 33, 633. (c) Gallop, M. A.: Barrett, R. W.; Dower, W. J.: Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233, 1385.
25. Such syntheses have been christened "mutiplex syntheses". Mitscher. L. A. Chemtracts: Org. Chem. 1995, 8, 19.
26. All the products are known compounds. Giese. B. Angew. Chem. 1983, 95, 771.
27. The reagents may also find use in the liquid phase synthesis of mixtures. See: Carell, T.: Wintner, E. A.: Sutherland, A. J.: Rebek, J., Jr.; Dunayevskiy, Y. M.: Vouros, P. Chem. Biol. 1995, 2, 171.
28. For a discussion of the possibilities for liquid phase combinatorial synthesis, see: Curran, D. P. Chemiracts: Org. Chem., in press.