The palladium-catalyzed trifluoromethylation of aryl chlorides

Science

Volumn 328, Issue 5986, 2010, Pages 1679-1681

  Cho, Eun Jin ^a   Senecal, Todd D ^a   Kinzel, Tom ^a   Zhang, Yong ^a   Watson, Donald A ^a,b   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; AMIDE; AMINE; CHLORIDE; ESTER; ETHER DERIVATIVE; NITRILE; PALLADIUM;

AGROCHEMICAL; CATALYSIS; CHLORIDE; METHYLATION; ORGANIC COMPOUND; PALLADIUM; REACTION KINETICS; SUBSTRATE; TRANSFORMATION;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; METHYLATION; PRIORITY JOURNAL;

CATALYSIS; FLUOROBENZENES; HYDROCARBONS, CHLORINATED; HYDROCARBONS, FLUORINATED; LIGANDS; METHYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM;

EID: 77954055124     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1190524     Document Type: Article

References (32)

1. D. Cartwright, in Organofluorine Chemistry, R. E. Banks, B. E. Smart, J. C. Tatlow, Eds. (Plenum, New York, 1994), pp. 237-262.
2. P. Kirsch, Modern Fluoroorganic Chemistry (Wiley-VCH, Weinheim, Germany, 2004).
3. K. Müller, C. Faeh, F. Diederich, Science 317, 1881 (2007).
4. A. M. Thayer, Chem. Eng. News 84, 15 (2006).
5. F. Swarts, Bull. Soc. Chim. Belg. 24, 309 (1892).
6. V. C. R. Mcloughlin, J. Thrower, Tetrahedron 25, 5921 (1969).
7. Y. Kobayashi, I. Kumadaki, Tetrahedron Lett. 10, 4095 (1969).
8. N. V. Kondratenko, E. P. Vechirko, L. M. Yagupolskii, Synthesis 1980, 932 (1980).
9. K. Matsui, E. Tobita, M. Ando, K. Kondo, Chem. Lett. 10, 1719 (1981).
10. D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 108, 832 (1986).
11. G. E. Carr, R. D. Chambers, T. F. Holmes, D. G. Parker, Perkin Trans. 1 1988, 921 (1988).
12. J. H. Clark, M. A. Mcclinton, R. J. Blade, Chem. Commun. 1988, 638 (1988).
13. O. Y. Chen, S. W. Wu, Chem. Commun. 1989, 705 (1989).
14. H. Urata, T. Fuchikami, Tetrahedron Lett. 32, 91 (1991).
15. F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327 (2002).
16. G. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 130, 8600 (2008).
17. M. Oishi, H. Kondo, H. Amii, Chem. Commun. (Cambridge) 2009, 1909 (2009).
18. D. A. Culkin, J. F. Hartwig, Organometallics 23, 3398 (2004).
19. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 128, 4632 (2006).
20. N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 132, 2878 (2010).
21. V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 128, 12644 (2006).
22. D. Naumann et al., Z. Anorg. Allg. Chem. 630, 746 (2004).
23. W. Tyrra et al., Chemistry 11, 6514 (2005).
24. X. Wang, L. Truesdale, J. Q. Yu, J. Am. Chem. Soc. 132, 3648 (2010).
25. B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc. 130, 13552 (2008).
26. D. A. Watson et al., Science 325, 1661 (2009); published online 13 August 2009 (10.1126/science.1178239).
27. Supporting material is available on Science Online.
28. J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc. 126, 13028 (2004).
29. M. J. Frisch et al., Gaussian 03, Revision E.01 (Gaussian, Inc., Wallingford CT, 2004).
30. The employed level of theory is B3LYP/6-311++G(2d,p)/ LanL2Dz//B3LYP/6-31G(d)/LanL2Dz.
31. ORTEP, www.ornl.gov/sci/ortep/ortep.html.
32. We thank the NIH for financial support of this project (grant GM46059) and Merck, Nippon Chemical, Boehringer Ingelheim, and BASF for gifts of chemicals and additional funds. T.K. thanks the Alexander von Humboldt Foundation for a Feodor Lynen postdoctoral fellowship. The Varian NMR instrument that we used was supported by the NSF (grants CHE 9808061 and DBI 9729592). We also thank P. Müller (MIT Chemistry Department, X-Ray Diffraction Facility) for obtaining the crystal structures of 13a and 13b. Cambridge Crystallography Data Centre (CCDC) 771779 and 771780 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the CCDC via www.ccdc.cam.ac.uk/data-request/cif.