Palladium-Catalyzed Arylation of Fluoroalkylamines

Journal of the American Chemical Society

Volumn 137, Issue 26, 2015, Pages 8460-8468

  Brusoe, Andrew T ^a   Hartwig, John F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; METAL HALIDES; REACTION KINETICS; SULFUR COMPOUNDS;

CATALYST LOADINGS; CROSS COUPLING REACTIONS; ELECTRON-WITHDRAWING SUBSTITUENTS; ELECTRONWITHDRAWING; FLUOROALKYL GROUP; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED ARYLATION; REDUCTIVE ELIMINATION;

CHEMICAL REACTIONS;

ALIPHATIC AMINE; AMIDE; ANILINE DERIVATIVE; BROMINE DERIVATIVE; CHLORIDE; FLUOROALKYLAMINE DERIVATIVE; NITROGEN; PALLADIUM; SULFONAMIDE; UNCLASSIFIED DRUG; AMINE; ANILINE; BROMIDE; CARBON; ETORICOXIB; FLUORINE; PHENOL; PYRIDINE DERIVATIVE; SULFONE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CROSS COUPLING REACTION; DECOMPOSITION; ELECTRON; OXIDATION KINETICS; REACTION ANALYSIS; REACTION TIME; SURFACE PROPERTY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; KINETICS; ORGANIC CHEMISTRY; PROCEDURES;

AMIDES; AMINES; ANILINE COMPOUNDS; BROMIDES; CARBON; CATALYSIS; CHEMISTRY, ORGANIC; CHLORIDES; ELECTRONS; FLUORINE; KINETICS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM; PHENOL; PYRIDINES; SULFONES;

EID: 84936805228     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02512     Document Type: Article

References (63)

1. The Chemistry of Anilines; Rappoport, Z., Ed.; Wiley: New York, 2007; Vol. 1.
2. McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348
3. Schiødt, F. V.; Rochling, F. A.; Casey, D. L.; Lee, W. M. N. Engl. J. Med. 1997, 337, 1112
4. Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 17
5. Perkin, W. H. Proc. R. Soc. London 1862, 12, 713
6. Sousa, M. M.; Melo, M. J.; Parola, A. J.; Morris, P. J. T.; Rzepa, H. S.; de Melo, J. S. S. Chem.-Eur. J. 2008, 14, 8507
7. Hartwig, J. F.; Shekhar, S.; Shen, Q.; Barrios-Landeros, F. PATAIS Chemistry of Functional Groups; John Wiley & Sons, Ltd.: New York, 2009.
8. Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611
9. Wis̈niewska-Knypl, J. M.; Jablońska, J. K.; Piotrowski, J. K. Br. J. Ind. Med. 1975, 32, 42
10. French, C. L.; Yaun, S.-S.; Baldwin, L. A.; Leonard, D. A.; Zhao, X. Q.; Calabrese, E. J. J. Appl. Toxicol. 1995, 15, 167
11. Wu, X.; Kannan, S.; Sadagopa Ramanujam, V. M.; Firoze Khan, M. J. Toxicol. Environ. Health A 2005, 68, 657
12. Bhakta, M.; Hollenberg, P. F.; Wimalasena, K. Chem. Commun. 2005, 2, 265
13. Fauber, B. P.; de Leon Boenig, G.; Burton, B.; Eidenschenk, C.; Everett, C.; Gobbi, A.; Hymowitz, S. G.; Johnson, A. R.; Liimatta, M.; Lockey, P.; Norman, M.; Ouyang, W.; René, O.; Wong, H. Bioorg. Med. Chem. Lett. 2013, 23, 6604
14. Phillips, B.; Cai, R.; Delaney, W.; Du, Z.; Ji, M.; Jin, H.; Lee, J.; Li, J.; Niedziela-Majka, A.; Mish, M.; Pyun, H.-J.; Saugier, J.; Tirunagari, N.; Wang, J.; Yang, H.; Wu, Q.; Sheng, C.; Zonte, C. J. Med. Chem. 2014, 57, 2161
15. Steinman, M.; Topliss, J. G.; Alekel, R.; Wong, Y.-S.; York, E. E. J. Med. Chem. 1973, 16, 1354
16. Van Oeveren, A.; Pio, B. A.; Tegley, C. M.; Higuchi, R. I.; Wu, M.; Jones, T. K.; Marschke, K. B.; Negro-Vilar, A.; Zhi, L. Bioorg. Med. Chem. Lett. 2007, 17, 1523
17. Xue, F.; Li, H.; Delker, S. L.; Fang, J.; Martásek, P.; Roman, L. J.; Poulos, T. L.; Silverman, R. B. J. Am. Chem. Soc. 2010, 132, 14229
18. Andersch, W.; Curtis, D.; Guan, S.; Guilhabert-Goya, M.; Royalty, R. N.; Springer, B.; Thielert, W.; Zhu, H. U.S. Patent 201422821, August 14, 2014.
19. Hell, S.; Belov, V.; Mitronova, G.; Bossi, M.; Moneron, G.; Wurm, C.; Jakobs, S.; Eggeling, C.; Bierwagen, J.; Meyer, L. U.S. Patent 2012135459, May 31, 2012.
20. Metais, E.; Sabelle, S. U.S. Patent 2006021157, February 2, 2006.
21. Mimura, H.; Kawada, K.; Yamashita, T.; Sakamoto, T.; Kikugawa, Y. J. Fluor. Chem. 2010, 131, 477
22. Francotte, P.; Goffin, E.; Fraikin, P.; Lestage, P.; Van Heugen, J.-C.; Gillotin, F.; Danober, L.; Thomas, J.-Y.; Chiap, P.; Caignard, D.-H.; Pirotte, B.; de Tullio, P. J. Med. Chem. 2010, 53, 1700
23. Ormazábal-Toledo, R.; Contreras, R.; Tapia, R. A.; Campodónico, P. R. Org. Biomol. Chem. 2013, 11, 2302
24. Wiedemann, S. H.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2006, 71, 1969
25. Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001
26. Tao, C.-Z.; Li, J.; Fu, Y.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2008, 49, 70
27. Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451
28. Henderson, J. L.; Buchwald, S. L. Org. Lett. 2010, 12, 4442
29. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534
30. Barluenga, J.; Bayón, A. M.; Asensio, G. J. Chem. Soc., Chem. Commun. 1983, 19, 1109
31. Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359
32. Hoi, K. H.; Organ, M. G. Chem.-Eur. J. 2012, 18, 804
33. Alcazar-Roman, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 12905
34. Shekhar, S.; Hartwig, J. F. Organometallics 2007, 26, 340
35. Schulte, J., II; Tweedie, S. Synlett 2007, 2331
36. Singer, R. A.; Doré, M.; Sieser, J. E.; Berliner, M. A. Tetrahedron Lett. 2006, 47, 3727
37. Withbroe, G. J.; Singer, R. A.; Sieser, J. E. Org. Process Res. Dev. 2008, 12, 480
38. Crawford, S. M.; Lavery, C. B.; Stradiotto, M. Chem.-Eur. J. 2013, 19, 16760
39. Kotecki, B. J.; Fernando, D. P.; Haight, A. R.; Lukin, K. A. Org. Lett. 2009, 11, 947
40. Gowrisankar, S.; Sergeev, A. G.; Anbarasan, P.; Spannenberg, A.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 11592
41. Love, P.; Cohen, R. B.; Taft, R. W. J. Am. Chem. Soc. 1968, 90, 2455
42. Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626
43. Podolskii, A. V.; German, L. S.; Knunyants, I. L. Bull. Acad. Sci. USSR Div. Chem. Sci. 1967, 16, 1092
44. Molloy, B. B.; Fuller, R. W. Biochemistry Involving Carbon-Fluorine Bonds; ACS Symposium Series 28; American Chemical Society: Washington, DC, 1976; pp 77-98.
45. Park, N. H.; Vinogradova, E. V.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 10.1002/anie.201502626
46. Lavery, C. B.; Rotta-Loria, N. L.; McDonald, R.; Stradiotto, M. Adv. Synth. Catal. 2013, 355, 981
47. Christmann, U.; Pantazis, D. A.; Benet-Buchholz, J.; McGrady, J. E.; Maseras, F.; Vilar, R. J. Am. Chem. Soc. 2006, 128, 6376
48. Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. Organometallics 2007, 26, 2183
49. Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 12003
50. Maimone, T. J.; Milner, P. J.; Kinzel, T.; Zhang, Y.; Takase, M. K.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 18106
51. Bordwell, F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424
52. Ferretti, A. C.; Mathew, J. S.; Ashworth, I.; Purdy, M.; Brennan, C.; Blackmond, D. G. Adv. Synth. Catal. 2008, 350, 1007
53. Klinkenberg, J. L.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11830
54. Hartwig, J. F. Inorg. Chem. 2007, 46, 1936
55. Ruiz-Castillo, P.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 3085
56. Hartwig, J. Organotransition Metal Chemistry. From Bonding to Catalysis; University Science Books: Sausalito, CA, 2010.
57. Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794
58. Driver, M. S.; Hartwig, J. F. Organometallics 1997, 16, 5706
59. Biscoe, M. R.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7232
60. Tardiff, B. J.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. J. Org. Chem. 2011, 77, 1056
61. Sunesson, Y.; Limé, E.; Nilsson Lill, S. O.; Meadows, R. E.; Norrby, P.-O. J. Org. Chem. 2014, 79, 11961
62. Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109
63. Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827