A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides

Angewandte Chemie - International Edition

Volumn 50, Issue 16, 2011, Pages 3793-3798

  Morimoto, Hiroyuki ^a   Tsubogo, Tetsu ^a   Litvinas, Nichole D ^a   Hartwig, John F ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Aryl halide; Copper; Cross coupling; Trifluoromethylation

Indexed keywords

ARYL BROMIDES; ARYL HALIDES; ARYL IODIDES; CROSS-COUPLINGS; HETEROAROMATIC SYSTEMS; IN-SITU; PHENANTHROLINE COMPLEXES; TRIFLUOROMETHYL; TRIFLUOROMETHYLATION;

BROMINE COMPOUNDS; COPPER; IODINE;

METAL HALIDES;

BROMIDE; COORDINATION COMPOUND; COPPER; FLUORINE; IODIDE; PHENANTHROLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMISTRY; METHYLATION;

ALKYLATION; BROMIDES; COORDINATION COMPLEXES; COPPER; FLUORINE; IODIDES; METHYLATION; PHENANTHROLINES;

EID: 79953675070     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100633     Document Type: Article

References (40)

1. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330.
2. For approaches to trifluoromethylation of aryl halides, see the following and reference [3]: a) E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679-1681;
3. b) V. V. Grushin, W. J. Marshall, J. Am. Chem. Soc. 2006, 128, 12644-12645;
4. c) T. Kitazume, N. Ishikawa, Chem. Lett. 1982, 137-140;
5. d) F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088-7105;
6. Angew. Chem. Int. Ed. 2009, 48, 6954-6971;
7. e) D. M. Wiemers, D. J. Burton, J. Am. Chem. Soc. 1986, 108, 832-834;
8. f) F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330;
9. g) A. Kütt, V. Movchun, T. Rodima, T. Dansauer, E. B. Rusanov, I. Leito, I. Kaljurand, J. Koppel, V. Pihl, I. Koppel, G. Ovsjannikov, L. Toom, M. Mishima, M. Medebielle, E. Lork, G.-V. Roschenthaler, I. A. Koppel, A. A. Kolomeitsev, J. Org. Chem. 2008, 73, 2607-2620;
10. h) G. G. Dubinina, H. Furutachi, D. A. Vicic, J. Am. Chem. Soc. 2008, 130, 8600-8601;
11. i) G. G. Dubinina, J. Ogikubo, D. A. Vicic, Organometallics 2008, 27, 6233-6235.
12. M. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909-1911.
13. For recent developments in trifluoromethylation of arenes, see: a) N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 2878-2879;
14. b) X. S. Wang, L. Truesdale, J. Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648-3649.
15. For recent developments in trifluoromethylation of aryl boronic acids, see: a) T. D. Senecal, A. T. Parsons, S. L. Buchwald, J. Org. Chem. 2011, 76, 1174-1176;
16. b) L. Chu, F.-L. Qing, Org. Lett. 2010, 12, 5060-5063.
17. For a copper-catalyzed trifluoromethylation of aryl halides that appeared during the processing of this manuscript, see: T. Knauber, F. Arikan, G.-V. Röschenthaler, L. J. Gooßen, Chem. Eur. J. 2011, 17, 2689-2697.
18. D. J. Burton, Z. Y. Yang, Tetrahedron 1992, 48, 189-275.
19. H. Urata, T. Fuchikami, Tetrahedron Lett. 1991, 32, 91-94.
20. a) R. Giri, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 15860-15863;
21. b) J. W. Tye, Z. Weng, A. M. Johns, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 9971-9983;
22. (c) J. W. Tye, Z. Q. Weng, R. Giri, J. F. Hartwig, Angew. Chem. 2010, 122, 2231-2235;
23. Angew. Chem. Int. Ed. 2010, 49, 2185-2189.
24. T. Tsuda, T. Hashimoto, T. Saegusa, J. Am. Chem. Soc. 1972, 94, 658-659.
25. For isolation of the only prior ligated copper-trifluoromethyl compound, see references [2h] and [2i].
26. 3 species by NMR spectroscopy in reference [2e], but this compound has not been isolated and fully characterized.
27. R. Krishnamurti, D. R. Bellew, G. K. S. Prakash, J. Org. Chem. 1991, 56, 984-989.
28. 4OMe as internal standard. Substrate 3b gave 4b in 36%yield. Substrate 3c gave 4c in 43%yield. Substrate 3g gave 4g in approximately 10% yield with the trifluoromethyl carbinols as the major products. Substrate 3e gave none of 4e and formed exclusively the trifluoromethyl carbinol product. 3p gave 4p in 41% yield; 3o gave 4o in 43% yield. Substrates 3l and 3m gave 4l and 4m in 17 and 39% yield.
29. W. W. Lin, O. Baron, P. Knochel, Org. Lett. 2006, 8, 5673-5676.
30. S. Kobayashi, H. Ishitani, Patent US 6476250 B1, 2002.
31. T. R. Wu, L. X. Shen, J. M. Chong, Org. Lett. 2004, 6, 2701-2704.
32. Q. Y. Chen, S. W. Wu, J. Chem. Soc. Chem. Commun. 1989, 705-706.
33. G. E. Carr, R. D. Chambers, T. F. Holmes, D. G. Parker, J. Chem. Soc. Perkin Trans. 1 1988, 921-926.
34. J. C. Xiao, C. F. Ye, J. M. Shreeve, Org. Lett. 2005, 7, 1963-1965.
35. G. O. Jones, P. Liu, K. N. Houk, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 6205-6213.
36. A. Annunziata, C. Galli, M. Marinelli, T. Pau, Eur. J. Org. Chem. 2001, 1323-1329.
37. A. N. Abeywickrema, A. L. J. Beckwith, J. Chem. Soc. Chem. Commun. 1986, 464-465.
38. R. J. Enemærke, T. B. Christensen, H. Jensen, K. Daasbjerg, J. Chem. Soc. Perkin Trans. 2 2001, 1620-1630.
39. N. Takeda, P. V. Poliakov, A. R. Cook, J. R. Miller, J. Am. Chem. Soc. 2004, 126, 4301-4309.
40. C. P. Andrieux, J. M. Saveant, D. Zann, New J. Chem. 1984, 8, 107-116.