Photocatalytic C-F alkylation; Facile access to multifluorinated arenes

Chemical Science

Volumn 6, Issue 12, 2015, Pages 7206-7212

  Singh, A ^a   Kubik, J J ^a   Weaver, J D ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AROMATIC COMPOUNDS; BOND LENGTH; BOND STRENGTH (CHEMICAL); FLUORINE COMPOUNDS; NITROGEN COMPOUNDS; SUBSTRATES;

C-C BONDS; C-F BONDS; FACILE ACCESS; FUNCTIONALIZATIONS; MILD REACTION CONDITIONS; PHOTO-CATALYTIC; REDUCTIVE ALKYLATION; SYNTHETIC TRANSFORMATIONS;

SULFUR COMPOUNDS;

EID: 84946915238     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c5sc03013g     Document Type: Article

References (69)

1. J. Wang M. Sanchez-Rosello J. L. Acena C. Del Pozo A. E. Sorochinsky S. Fustero V. A. Soloshonok H. Liu Chem. Rev. 2014 114 2432 2506
2. G. Theodoridis, in Advances in Fluorine Science, ed., T. Alain, Elsevier, 2006, vol. 2, pp. 121-175
3. New FDA approved drugs in 2013, http://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DrugInnovation/UCM381803.pdf
4. The pesticide manual: a world compendium, ed. C. Tomlin, British Crop Protection Council, Farnham, 2000, vol. 12
5. M. C. R. Alavanja Rev. Environ. Health 2009 24 303 309
6. R. E. Banks, Fluorine in agriculture, papers from a three-day conference held at UMIST, Manchester, UK, 1995
7. P. S. Fier J. F. Hartwig Science 2013 342 956 960
8. K. S. L. Chan M. Wasa X. Wang J.-Q. Yu Angew. Chem., Int. Ed. 2011 50 9081 9084
9. D. A. Watson M. Su G. Teverovskiy Y. Zhang J. García-Fortanet T. Kinzel S. L. Buchwald Science 2009 325 1661 1664
10. Y. Ye S. D. Schimler P. S. Hanley M. S. Sanford J. Am. Chem. Soc. 2013 135 16292 16295
11. N. Ichiishi A. J. Canty B. F. Yates M. S. Sanford Org. Lett. 2013 15 5134 5137
12. P. Tang T. Furuya T. Ritter J. Am. Chem. Soc. 2010 132 12150 12154
13. P. S. Fier J. Luo J. F. Hartwig J. Am. Chem. Soc. 2013 135 2552 2559
14. T. Ahrens J. Kohlmann M. Ahrens T. Braun Chem. Rev. 2015 115 931 972
15. J. L. Kiplinger T. G. Richmond C. E. Osterberg Chem. Rev. 1994 94 373 431
16. H. Amii K. Uneyama Chem. Rev. 2009 109 2119 2183
17. S. I. Konovalov, RU2209198C2, 2003
18. A. V. Dushkin, V. S. Kobrin, L. M. Karnatovskaya, V. V. Knyazev, V. N. Kobrina, S. Z. Kusov, S. V. Pavlov, A. E. Grazhdannikov, E. N. Chabueva, V. V. Boldyrev, V. A. Matyukha, V. F. Starichenko, G. A. Tolstikov and G. P. Khandorin, RU2165404C1, 2001
19. M. Armand, J.-M. Tarascon, N. Recham, S. Grugeon, S. Laruelle and S. Devaraj, WO2009122044A2, 2009
20. S. J. Blanksby G. B. Ellison Acc. Chem. Res. 2003 36 255 263
21. F. H. Allen O. Kennard D. G. Watson L. Brammer A. G. Orpen R. Taylor J. Chem. Soc., Perkin Trans. 2 1987 S1 S19 10.1039/P298700000S1
22. D. M. Lemal J. Org. Chem. 2004 69 1 11
23. D. Lentz T. Braun M. F. Kuehnel Angew. Chem., Int. Ed. Engl. 2013 52 3328 3348
24. E. Clot O. Eisenstein N. Jasim S. A. Macgregor J. E. McGrady R. N. Perutz Acc. Chem. Res. 2011 44 333 348
25. H. Torrens Coord. Chem. Rev. 2005 249 1957 1985
26. J. Weaver S. Senaweera Tetrahedron 2014 70 7413 7428
27. A. D. Sun J. A. Love Dalton Trans. 2010 39 10362 10374
28. T. Braun F. Wehmeier Eur. J. Inorg. Chem. 2011 2011 613 625
29. A. D. Sun K. Leung A. D. Restivo N. A. LaBerge H. Takasaki J. A. Love Chem.-Eur. J. 2014 20 3162 3168
30. A. D. Sun J. A. Love J. Fluorine Chem. 2010 131 1237 1240
31. T. Wang J. A. Love Organometallics 2008 27 3290 3296
32. T. Wang B. J. Alfonso J. A. Love Org. Lett. 2007 9 5629 5631
33. L. A. Wall J. E. Fearn W. J. Pummer J. M. Antonucci J. Res. Natl. Bur. Stand., Sect. A 1963 67 481
34. Y. Sun H. Sun J. Jia A. Du X. Li Organometallics 2014 33 1079 1081
35. J. M. Birchall R. N. Haszeldine J. Chem. Soc. 1961 3719 3727 10.1039/JR9610003719
36. W. Lu J. Gao J.-K. Yang L. Liu Y. Zhao H.-C. Wu Chem. Sci. 2014 5 1934 1939
37. J. M. R. Narayanam J. W. Tucker C. R. J. Stephenson J. Am. Chem. Soc. 2009 131 8756 8757
38. M. Cherevatskaya M. Neumann S. Fueldner C. Harlander S. Kuemmel S. Dankesreiter A. Pfitzner K. Zeitler B. Koenig Angew. Chem., Int. Ed. 2012 51 4062 4066
39. J. W. Tucker J. M. R. Narayanam S. W. Krabbe C. R. J. Stephenson Org. Lett. 2010 12 368 371
40. J. W. Tucker J. D. Nguyen J. M. R. Narayanam S. W. Krabbe C. R. J. Stephenson Chem. Commun. 2010 46 4985 4987
41. S. Paria V. Kais O. Reiser Adv. Synth. Catal. 2014 356 2853 2858
42. J. D. Nguyen E. M. D'Amato J. M. R. Narayanam C. R. J. Stephenson Nat. Chem. 2012 4 854 859
43. S. M. Senaweera A. Singh J. D. Weaver J. Am. Chem. Soc. 2014 136 3002 3005
44. M. B. Yim D. E. Wood J. Am. Chem. Soc. 1976 98 2053 2059
45. R. A. Rossi Acc. Chem. Res. 1982 15 164 170
46. J. F. Bunnett Acc. Chem. Res. 1978 11 413 420
47. G. Reginato M. P. Catalani B. Pezzati R. Di Fabio A. Bernardelli O. Curcuruto E. Moro A. Pozzan A. Mordini Org. Lett. 2015 17 398 401
48. G. A. Molander, in Radicals in Organic Synthesis, Wiley-VCH Verlag GmbH, 2008, ch. 9, pp. 153-182, 10.1002/9783527618293
49. H. Ismaili S. P. Pitre J. C. Scaiano Catal. Sci. Technol. 2013 3 935 937
50. C. K. Prier D. A. Rankic D. W. C. MacMillan Chem. Rev. 2013 113 5322 5363
51. D. M. Schultz T. P. Yoon Science 2014 343
52. J. M. R. Narayanam C. R. J. Stephenson Chem. Soc. Rev. 2011 40 102 113
53. I. P. Beletskaya G. A. Artamkina A. Y. Mil'chenko P. K. Sazonov M. M. Shtern J. Phys. Org. Chem. 1996 9 319 328
54. U. Pischel X. Zhang B. Hellrung E. Haselbach P.-A. Muller W. M. Nau J. Am. Chem. Soc. 2000 122 2027 2034
55. K. Okamoto K. Ohkubo K. M. Kadish S. Fukuzumi J. Phys. Chem. A 2004 108 10405 10413
56. R. A. Marcus J. Phys. Chem. B 1998 102 10071 10077
57. Modest yields are due, in part, to loss during the isolation because of the highly fluorinated nature of the substrates which increases their relative volatility. Additionally, some byproducts are commonly observed which also decrease the yield, such as; the HDF product, the alkylated product which has undergone subsequent HDF, and in cases of more electrophilic fluoroarenes, N-substitution from the DIPEA
58. M. Lafrance D. Shore K. Fagnou Org. Lett. 2006 8 5097 5100
59. K. S. Gant L. G. Christophorou J. Chem. Phys. 1976 65 2977 2981
60. J. Mortensen J. Heinze Angew. Chem., Int. Ed. 1984 23 84 85
61. J. A. Marsella A. G. Gilicinski A. M. Coughlin G. P. Pez J. Org. Chem. 1992 57 2856 2860
62. 3-Cl-tetrafluoropyridine is a commercially available byproduct of incomplete fluorination in the halex process, G. G. Yakobson and I. L. Knunyants, Syntheses of fluoroorganic compounds, Springer-Verlag, Berlin; New York, 1985
63. M. Newcomb Tetrahedron 1993 49 1151 1176
64. A. L. J. Beckwith G. Moad J. Chem. Soc., Perkin Trans. 2 1980 1083 1092 10.1039/P29800001083
65. H. Chen, Y. Chu, S. Do, A. Estrada, B. Hu, A. Kolesnikov, X. Lin, J. P. Lyssikatos, D. Shore, V. Verma, L. Wang, G. Wu and P.-W. Yuen, WO2015052264A1, 2015
66. E. L. Strangeland, L. J. Patterson and S. Zipfel, US pat., US20110230495A1, 2011
67. U. Petersen, T. Schenke, K. Grohe, M. Schriewer, I. Haller, K. G. Metzger, R. Endermann and H. J. Zeiler, EP326916A2, 1989
68. S. Senaweera J. D. Weaver J. Org. Chem. 2014 79 10466 10476
69. J. M. Birchall R. Hazard R. N. Haszeldine A. W. Wakalski J. Chem. Soc. C 1967 1967 47 50