Taming of fluoroform: Direct nucleophilic trifluoromethylation of Si, B, S, and C centers

Science

Volumn 338, Issue 6112, 2012, Pages 1324-1327

  Surya Prakash, G K ^a   Jog, Parag V ^a   Batamack, Patrice T D ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; CARBON; ELECTROPHILE; ETHER; FLUOROFORM; ORGANIC SOLVENT; POLITEF; POLYVINYLIDENE FLUORIDE; SILICON; TETRAHYDROFURAN; TOLUENE;

CARBON; DRUG; FUNCTIONAL CHANGE; GREENHOUSE GAS; METHYLATION; ORGANIC COMPOUND; SOLVENT; STOCHASTICITY; SULFUR; VOLUME;

ARTICLE; CHEMICAL REACTION; FLUORINE NUCLEAR MAGNETIC RESONANCE; FOAM; GREENHOUSE GAS; NUCLEOPHILIC TRIFLUOROMETHYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STOICHIOMETRY;

EID: 84870712049     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1227859     Document Type: Article

References (47)

1. K. Müller, C. Faeh, F. Diederich, Science 317, 1881 (2007).
2. As of 20 July 2012, based on the search performed in SciFinder Scholar with trifluoromethylation as research topic and number of articles published between 2008 and 2011.
3. G. K. S. Prakash, R. Krishnamurti, G. A. Olah, J. Am. Chem. Soc. 111, 393 (1989).
4. I. Ruppert, K. Schlich, W. Volbach, Tetrahedron Lett. 25, 2195 (1984).
5. G. K. S. Prakash, M. Mandal, J. Fluor. Chem. 112, 123 (2001).
6. G. K. S. Prakash, A. K. Yudin, Chem. Rev. 97, 757 (1997).
7. Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 134, 9034 (2012).
8. Y. Ye, S. H. Lee, M. S. Sanford, Org. Lett. 13, 5464 (2011).
9. N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 132, 2878 (2010).
10. E. J. Cho et al., Science 328, 1679 (2010).
11. G. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 130, 8600 (2008).
12. J. F. Hartwig, H. Morimoto, P. Fier (Univ. of Illinois, USA, 2012), pp. 60 U.S. Patent Appl. 20120226041.
13. H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. Int. Ed. 50, 3793 (2011).
14. F. Wang et al., Angew. Chem. Int. Ed. 50, 7153 (2011).
15. G. P. Stahly (Ethyl Corp., USA, 1989), pp. 9 U.S. Patent 4804774A.
16. G. P. Stahly, D. R. Bell, J. Org. Chem. 54, 2873 (1989).
17. T. Hagiwara, T. Kobayashi, T. Fuchikami, Nippon Kagaku Kaishi 1997, 869 (1997).
18. G. Pawelke, J. Fluor. Chem. 42, 429 (1989).
19. J. Grobe, J. Hegge, Synlett 1995, 641 (1995).
20. P. Ramaiah, R. Krishnamurti, G. K. S. Prakash, Org. Synth. 72, 232 (1995).
21. G. K. S. Prakash, A. K. Yudin, D. Deffieux, G. A. Olah, Synlett 1996, 151 (1996).
22. G. K. S. Prakash, J. Hu, G. A. Olah, J. Org. Chem. 68, 4457 (2003).
23. G. K. S. Prakash, J. Hu, G. A. Olah (Univ. of Southern California, USA, 2004), pp. 15 U.S. Patent 6,803,477.
24. W. Han, Y. Li, H. Tang, H. Liu, J. Fluor. Chem. 140, 7 (2012).
25. T. Shono, M. Ishifune, T. Okada, S. Kashimura, J. Org. Chem. 56, 2 (1991).
26. R. Barhdadi, M. Troupel, J. Perichon, Chem. Commun. (12): 1251 (1998).
27. B. Folleas, I. Marek, J.-F. Normant, J. L. Saint, Tetrahedron Lett. 39, 2973 (1998).
28. B. Folleas, I. Marek, J.-F. Normant, L. Saint-Jalmes, Tetrahedron 56, 275 (2000).
29. B. R. Langlois, T. Billard, Synthesis 2, 185 (2003).
30. B. R. Langlois, T. Billard, ACS Symp. Ser. 911, 57 (2005).
31. S. Large, N. Roques, B. R. Langlois, J. Org. Chem. 65, 8848 (2000).
32. A. Zanardi, M. A. Novikov, E. Martin, J. Benet-Buchholz, V. V. Grushin, J. Am. Chem. Soc. 133, 20901 (2011).
33. P. Novak, A. Lishchynskyi, V. V. Grushin, Angew. Chem. Int. Ed. 51, 7767 (2012).
34. P. Novák, A. Lishchynskyi, V. V. Grushin, J. Am. Chem. Soc. 134, 16167 (2012).
35. I. Popov, S. Lindeman, O. Daugulis, J. Am. Chem. Soc. 133, 9286 (2011).
36. G. K. S. Prakash, P. V. Jog, P. T. D. Batamack, G. A. Olah (Univ. of Southern California, USA, 2012), pp. 42 PCT. Int. Appl. WO2012148772A1.
37. T. Billard, B. R. Langlois, G. Blond, Eur. J. Org. Chem. 2001, 1467 (2001).
38. N. J. Rijs, R. A. J. O'Hair, Dalton Trans. 41, 3395 (2012).
39. T. Knauber, F. Arikan, G. V. Röschenthaler, L. J. Goossen, Chem. Eur. J. 17, 2689 (2011).
40. V. V. Levin, A. D. Dilman, P. A. Belyakov, M. I. Struchkova, V. A. Tartakovsky, Tetrahedron Lett. 52, 281 (2011).
41. B. A. Khan, A. E. Buba, L. J. Goossen, Chem. Eur. J. 18, 1577 (2012).
42. A. A. Kolomeitsev et al., Tetrahedron Lett. 44, 8273 (2003).
43. G. A. Molander, B. P. Hoag, Organometallics 22, 3313 (2003).
44. G. A. Olah, G. K. S. Prakash, A. Molnar, J. Sommer, Superacid Chemistry (Wiley, Hoboken, NJ, ed. 2, 2009).
45. R. E. Banks, Ed., Preparation, Properties, and Industrial Applications of Organofluorine Compounds (Ellis Horwood Ltd., Chichester, UK, 1982).
46. G. Forat, J.-M. Mas, L. Saint-Jalmes (Rhone-Poulenc Chimie SA, Fr. 1996), pp. 16 Eur. Patent 735023A1.
47. S. Mukhopadhyay, A. T. Bell, R. V. Srinivas, G. S. Smith, Org. Process Res. Dev. 8, 660 (2004).