Regio- and stereoselective allylic trifluoromethylation and fluorination using CuCF3 and CuF reagents

Journal of Organic Chemistry

Volumn 78, Issue 14, 2013, Pages 7330-7336

  Larsson, Johanna M ^a   Pathipati, Stalin R ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC CHLORIDE; CYCLIC SUBSTRATES; MECHANISTIC STUDIES; NUCLEOPHILIC SUBSTITUTIONS; SELECTIVE SYNTHESIS; STEREO-SELECTIVE; TRIFLUOROACETATES; TRIFLUOROMETHYLATION;

CHLORINE COMPOUNDS; COPPER; FLUORINATION; HALOGENATION; REACTION INTERMEDIATES;

FLUORINE;

ALLYL CHLORIDE; COPPER DERIVATIVE; REAGENT; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; FLUORINATION; METHYLATION; NUCLEOPHILICITY; STEREOCHEMISTRY; SYNTHESIS; TRIFLUOROMETHYLATION;

COPPER; FLUORIDES; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84880566058     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4010074     Document Type: Article

References (41)

1. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
2. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
3. Tomashenko, O. A.; Escudero-Adán, E. C.; Martínez Belmonte, M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655
4. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
5. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
6. Hafner, A.; Bräse, S. Adv. Synth. Catal. 2011, 353, 3044
7. Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536
8. Niedermann, K.; Früh, N.; Vinogradova, E.; Wiehn, M. S.; Moreno, A.; Togni, A. Angew. Chem., Int. Ed. 2011, 50, 1059
9. Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832
10. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174
11. Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882
12. Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. Chem. Commun. 2013, 10.1039/c3cc43357a
13. Egami, H.; Shimizu, R.; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503
14. Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458
15. Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120
16. Miyake, Y.; Ota, S.-i.; Nishibayashi, Y. Chem.-Eur. J. 2012, 18, 13255
17. Mizuta, S.; Galicia-López, O.; Engle, K. M.; Verhoog, S.; Wheelhouse, K.; Rassias, G.; Gouverneur, V. Chem.-Eur. J. 2012, 18, 8583
18. Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-López, O.; O'Duill, M.; Médebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250
19. Zhao, T. S. N.; Szabó, K. J. Org. Lett. 2012, 14, 3966
20. Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251
21. Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071
22. Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189
23. Gulliver, D. J.; Levason, W.; Webster, M. Inorg. Chim. Acta 1981, 52, 153
24. Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 17402
25. Benedetto, E.; Tredwell, M.; Hollingworth, C.; Khotavivattana, T.; Brown, J. M.; Gouverneur, V. Chem. Sci. 2013, 4, 89
26. Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. J. Am. Chem. Soc. 2011, 133, 19318
27. Lee, E.; Yandulov, D. V. J. Fluorine Chem. 2009, 130, 474
28. Zhang, Z.; Wang, F.; Mu, X.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2013, 10.1002/anie.201301891
29. Bäckvall, J.-E.; Nyström, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676
30. Hazari, A.; Gouverneur, V.; Brown, J. M. Angew. Chem., Int. Ed. 2009, 48, 1296
31. Madrahimov, S. T.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 8136
32. Brozek, L. A.; Ardolino, M. J.; Morken, J. P. J. Am. Chem. Soc. 2011, 133, 16778
33. Penjišević, J.; Šukalović, V.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V.; Roglić, G. Arch. Pharm. (Weinheim, Ger.) 2007, 340, 456
34. Vyas, D. J.; Oestreich, M. Chem. Commun. 2010, 46, 568
35. Eummer, J. T.; Gibbs, B. S.; Zahn, T. J.; Sebolt-Leopold, J. S.; Gibbs, R. A. Bioorg. Med. Chem. 1999, 7, 241
36. Sheffy, F. K.; Godschalx, J. P.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4833
37. Welle, A.; Petrignet, J.; Tinant, B.; Wouters, J.; Riant, O. Chem.-Eur. J. 2010, 16, 10980
38. Kunai, A.; Sakurai, T.; Toyoda, E.; Ishikawa, M. Organometallics 1996, 15, 2478
39. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583
40. Benedetto, E.; Keita, M.; Tredwell, M.; Hollingworth, C.; Brown, J. M.; Gouverneur, V. Organometallics 2012, 31, 1408
41. Shi, E.; Shao, Y.; Chen, S.; Hu, H.; Liu, Z.; Zhang, J.; Wan, X. Org. Lett. 2012, 14, 3384