Radical reactions with alkyl and fluoroalkyl ((fluorous) tin hydride reagents in supercritical CO2

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7406-7407

  Hadida, Sabine ^a   Super, Michael S ^b   Beckman, Eric J ^b   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b University of Pittsburgh   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE; ANTHRACENE DERIVATIVE; CYANIDE; INDOLE DERIVATIVE; RADICAL; REAGENT; STEROID;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; REDUCTION; TECHNIQUE;

EID: 0030849312     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971120i     Document Type: Article

References (32)

1. (a) Eckert, C. A.; Knutson, B. L.; Debenedetti, P. G. Nature 1996, 383, 313.
2. (b) Brennecke, J. F. Chem. Ind.-London 1996, 831.
3. (c) Phelps, C. L.; Smart, N. G.; Wai, C. M. J. Chem. Educ. 1996, 73, 1163.
4. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
5. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
6. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
7. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
8. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
9. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
10. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
11. 2. Baumann, W.; Kainz, J.; Koch, D.; Leitner, W. Angew. Chem., Int. Ed. Engl. In press. We thank Professor A. Pfalz for informing us of this work and Prof. W. Leitner for a preprint.
12. (a) Luque de Castro, M. D.; Valcarcel, M.; Tena M. T. Analytical Supercritical Fluid Extraction; Springer-Verlag: Berlin, 1994; p 41.
13. (b) McHugh, M. A.; Krukonis V. J. Supercritical Fluid Extraction: Principle and Practice; Butterworths: Stoneham, MA, 1994.
14. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986.
15. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 715 and 779.
16. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
17. (d) Motherwell, W.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
18. (a) Tanko, J. M.; Blackert, J. F. Science 1994, 263, 203.
19. (b) DeSimone, J. M.; Guan, Z.; Elsbernd, C. S. Science 1992, 257, 945.
20. (a) Horvath, I. T.; Rabai, J. Science 1994, 266, 72.
21. (b) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531.
22. (c) Dimagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312.
23. (d) Curran, D. P.; Hoshino, M. J. Org. Chem. 1996, 61, 6480.
24. (e) Studer, A.; Hadida, S.; Ferrito, R.; Kim, S.-Y.; Jäger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
25. McFann, G. J.; Johnston, K. P.; Hurter, P. N.; Hatton, T. A. IEC Res. 1993, 32, 2336.
26. The formate was identified by comparison with authentic material prepared by the direct reaction of bis(tributyltin)oxide with formic acid. Ohara, M.; Okawara, R. J. Organomet. Chem. 1965, 3, 484.
27. No tin formate was formed in an experiment conducted without AIBN.
28. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
29. Anionic carboxylations under electrochemical conditions: Sullenberger, E. F.; Dressman, S. F.; Michael, A. C. J. Phys. Chem. 1994, 98, 5347.
30. 2 phase. Heating of 10 and 4 with a minimal amount of benzotrifluoride (estimated concentration 0.6 M) provided the following yields: 11, 62%; 12, 6%; 10, 21%.
31. Curran, D. P.; Hadida, S.; Horner, J. H.; Martinez, F. N.; Newcomb, M. Tetrahedron Lett. 1997, 38, 2783.
32. Curran, D. P. Chemtracts - Org. Chem. 1996, 9, 75.