Innate C-H trifluoromethylation of heterocycles

Proceedings of the National Academy of Sciences of the United States of America

Volumn 108, Issue 35, 2011, Pages 14411-14415

  Ji, Yining ^a   Brueckl, Tobias ^a   Baxter, Ryan D ^a   Fujiwara, Yuta ^a   Seiple, Ian B ^a   Su, Shun ^a   Blackmond, Donna G ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

C H functionalization; Medicinal chemistry; Synthetic methodology

Indexed keywords

ALKENE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; NATURAL PRODUCT; PYRIDINE DERIVATIVE;

ARTICLE; ELECTRON; ENVIRONMENTAL TEMPERATURE; METHYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; TRIFLUOROMETHYLATION;

CARBON; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, FLUORINATED; HYDROGEN; METHYLATION;

EID: 80052298009     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1109059108     Document Type: Article

References (32)

1. Smart B.E. (1996) Introduction:Fluorine chemistry. Chem Rev 96:1555-1556.
2. Filler R, Kobayashi Y, Yagupolskii LM, eds. (1993) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications (Elsevier, Amsterdam).
3. Welch J.T. (1987) Advances in the preparation of biologically-active organofluorine compounds. Tetrahedron 43:3123-3197.
4. Ma J.A., Cahard D. (2007) Strategies for nucleophilic, electrophilic, and radical trifluoromethylations. J Fluorine Chem 128:975-996.
5. Meanwell N.A. (2011) Synopsis of some recent tactical application of bioisosteres in drug design. J Med Chem 54:2529-2591.
6. Furuya T., Kamlet A.S., Ritter T. (2011) Catalysis for fluorination and trifluoromethylation. Nature 473:470-477.
7. Wiehn M.S., Vinogradova E.V., Togni A. (2010) Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents. J Fluorine Chem 131:951-957.
8. Umemoto T., Ishihara S. (1993) Power-variable electrophilic trifluoromethylating agents. S-, Se-, and Te- (trifluoromethyl)dibenzothio-, -seleno-, and -tellurophenium salt system. J Am Chem Soc 115:2156-2164.
9. Prakash G.K., Yudin A.K. (1997) Perfluoroalkylation with organosilicon reagents. Chem Rev 97:757-786. (Pubitemid 127661198)
10. Roy S., Gregg B.T., Gribble G.W., Le V.D., Roy S. (2011) Trifluoromethylation of aryl and heteroaryl halides. Tetrahedron 67:2161-2195.
11. Tomashenko O.A., Grushin V.V. (2011) Aromatic trifluoromethylation with metal complexes. Chem Rev, 10.1021/cr1004293.
12. Oishi M., Kondo H., Amii H. (2009) Aromatic trifluoromethylation catalytic in copper. Chem Commun 14:1909-1911.
13. Knauber T., Arikan F., Roschenthaler G.V., Goossen L.J. (2011) Copper-catalyzed trifluoromethylation of aryl iodides with potassium (trifluoromethyl)trimethoxyborate. Chemistry 17:2689-2697.
14. Morimoto H., Tsubogo T., Litvinas N.D., Hartwig J.F. (2011) A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides. Angew Chem Int Ed Engl 50:3793-3798.
15. Chu L., Qing F.L. (2010) Copper-mediated oxidative trifluoromethylation of boronic acids. Org Lett 12:5060-5063.
16. Senecal T., Parsons A.T., Buchwald S.T. (2011) Room temperature aryl trifluoromethylation via copper-mediated oxidative cross-coupling. J Org Chem 76:1174-1176.
17. Cho E.J., et al. (2010) The palladium-catalyzed trifluoromethylation of aryl chlorides. Science 328:1679-1681.
18. Wang X., Truesdale L., Yu J.Q. (2010) Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter. J Am Chem Soc 132:3648-3649.
19. Seiple I.B., et al. (2010) Direct C-H arylation of electron-deficient heterocycles with arylboronic acids. J Am Chem Soc 132:13194-13196.
20. Fujiwara Y., et al. (2011) Practical C-H functionalization of quinones with boronic acids. J Am Chem Soc 133:3292-3295.
21. Kino T., et al. (2010) Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(III) compound, H2O2 and dimethylsulfoxide. J Fluorine Chem 131:98-105.
22. Langlois B.R., Laurent E., Roidot N. (1991) Trifluoromethylation of aromatic compounds with sodium trifluoromethanesulfinate under oxidative conditions. Tetrahedron Lett 32:7525-7528.
23. Langlois B.R., Laurent E., Roidot N. (1992) "Pseudo-cationic" trifluoromethylation of enol esters with sodium trifluoromethanesulfinate. Tetrahedron Lett 33:1291-1294.
24. Langlois B.R., Montegre D., Roidot N. (1994) Synthesis of S-trifluoromethyl-containing a-amino acids from sodium trifluoromethanesulfinate and dithio-amino acids. J Fluorine Chem 63-66.
25. Billard T., Roques N., Langlois B.R. (1999) Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides. J Org Chem 64:3813-3820.
26. 2: A detailed tertiary butyl oxidation mechanism. J Phys Chem 103:9731-9769.
27. 3I and its industrial applications. Appl Cat A General 342:137-143.
28. Kumar V., Malhotra S.V. (2008) Synthesis of nucleoside-based antiviral drugs in ionic liquids. Bioorg Med Chem Lett 18:5640-5642.
29. Bresser T., Monzon G., Mosrin M., Knochel P. (2010) Scaleable preparation of sensitive functionalized aromatics and heteroaromatics via directed metalation using tmpZnCl- LiCl. Org Process Res Dev 14:1299-1130.
30. Hirota K., Sako M.H. (1997) A high chemical reativity of 5-azidouracils and its synthetic application:Novel synthesis of 8-substituted 1,3-dimethylxanthine derivatives. Heterocycles 46:547-554. (Pubitemid 127740635)
31. Coe J.W., et al. (2005) Varenicline:An alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem 48:3474-3477. (Pubitemid 40664098)
32. Coe J.W., Watson H.A., Singer R.A. (2008) Varenicline: Discovery synthesis and process chemistry developments. Process Chemistry in the Pharmaceutical Industry, eds K Gadamasetti and T Braish (CRC Press, Boca Raton, FL), Vol 2, pp 23-47.