Visible light photocatalytic metal-free perfluoroalkylation of heteroarenes in continuous flow

Journal of Flow Chemistry

Volumn 4, Issue 1, 2014, Pages 12-17

  Straathof, Natan J W ^a   Van Osch, Dannie J G P ^a   Schouten, Arian ^a   Wang, Xiao ^b   Schouten, Jaap C ^a   Hessel, Volker ^a   Noël, Timothy ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

Eosin Y; Flow chemistry; Metal free; Perfluoroalkylation; Photochemistry; Photoredox catalysis; Trifluoromethylation

Indexed keywords

EID: 84981350369     PISSN: 2062249X     EISSN: 20630212     Source Type: Journal    
DOI: 10.1556/JFC-D-13-00032     Document Type: Article

References (51)

1. (a) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
2. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330.
3. (a) Mace, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2479-2494
4. (b) Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617-626
5. (c) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem. Int. Ed. 2013, 52, 8214-8264.
6. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 437, 470-477.
7. (a) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679-1681
8. (b) Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem. Int. Ed. 2011, 50, 3793-3798
9. (c) Danoun, G.; Bayarmagnai, B.; Grünberg, M. F.; Gooßen, L. J. Angew. Chem. Int. Ed. 2013, 52, 7972-7975
10. (d) Seo, S.; Taylor, J. B.; Greaney, M. F. Chem. Commun. 2013, 49, 6385-6387
11. (e) Wang, X.; Xu, Y.; Mo, F.; Ji, G.; Qiu, D.; Feng, J.; Ye, Y.; Zhang, S.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2013, 135, 10330-10333.
12. Studer, A. Angew. Chem. Int. Ed. 2012, 51, 8950-8958.
13. (a) Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875-10877
14. (b) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224-228
15. (c) Pham, P. V.; Nagib, D. A.; MacMillan, D. W. C. Angew. Chem. Int. Ed. 2011, 50, 6119-6122
16. (d) Iqbal, N.; Choi, S.; Ko, E.; Cho, E. J. Tetrahedron Lett. 2012, 53, 2005-2008
17. (e) Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383-11387
18. (f) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2013, 134, 9034-9037
19. (g) Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem. Eur. J. 2013, 19, 6209-6212
20. (h) Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-Lopez, O.; O'Duill, M.; Medebielle, M.; Wheelhouse, K.; Rassias, G.; Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250-1253
21. (i) Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; O'Duill, M.; Wheelhouse, K.; Rassias, G.; Medebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505-2508
22. (j) Iqbal, N.; Jung, J.; Park, S.; Cho, E. J. Angew. Chem. Int. Ed. 2014, 53, 539-542.
23. (a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
24. (b) Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617-1722
25. (c) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
26. (d) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387-2403
27. (e) Reckenthaler, M.; Griesbeck, A. G. Adv. Synth. Catal. 2013, 355, 2727-2744.
28. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Modern molecular photochemistry of organic molecules; University Science Books, Sausalito, California, 2010.
29. Straathof, N. J. W.; Gemoets, H. P. L.; Wang, X.; Schouten, J. C.; Hessel, V.; Noel, T. ChemSusChem 2014, DOI: 10.1002/cssc.201301282
30. (a) Neumann, M.; Zeitler, K. Org. Lett. 2012, 14, 2658-2661
31. (b) Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J. Angew. Chem. Int. Ed. 2012, 51, 4144-4147
32. (c)Wang, X.; Cuny, G. D.; Noel, T. Angew. Chem. Int. Ed. 2013, 52, 7860-7864
33. (d) Nguyen, J. D.; Reiß, B.; Dai, C.; Stephenson, C. R. J. Chem. Commun. 2013, 49, 4352-4354
34. (e) Rueping, M.; Vila, C.; Bootwicha, T. ACS Catal. 2013, 3, 1676-1680.
35. (a) Van Gerven, T.; Mul, G.; Moulijn, J.; Stankiewicz, A. Chem. Eng. Proc. 2007, 46, 781-789
36. (b) Oelgemoeller, M. Chem. Eng. Technol. 2012, 35, 1144-1152
37. (c) Knowles, J. P.; Elliott, L. D.; Booker-Milburn, K. I. Beilstein J. Org. Chem. 2012, 8, 2025-2052.
38. Noel, T.; Wang, X.; Hessel, V. Chim. Oggi 2013, 31 (3, suppl.), 10-14.
39. (a) Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889-900
40. (b) Thayer, A. Chem. Eng. News 2005, 83, 55-58.
41. (a) Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97-113
42. (b) Fukuzumi, S.; Ohkubo, K. Chem. Sci. 2013, 4, 561-574.
43. (a) Cui, L.; Matusaki, Y.; Tada, N.; Miura, T.; Uno, B.; Itoh, A. Adv. Synth. Catal. 2013, 355, 2203-2207
44. (b) Grandjean, J.-M. M.; Nicewicz, D. A. Angew. Chem. Int. Ed. 2013, 52, 3967-3971
45. (c) Perkowski, A. J.; Nicewicz, D. A. J. Am. Chem. Soc. 2013, 135, 10334-10337
46. (d) Teo, Y. C.; Pan, Y.; Tan, C. H. ChemCatChem 2013, 5, 235-240
47. (e) Neumann, M.; Zeitler, K. Chem. Eur. J. 2013, 19, 6950-6955.
48. Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104-3107.
49. Noel, T.; Hessel, V. ChemSusChem 2013, 6, 405-407.
50. Yue, J.; Chen, G.; Yuan, Q.; Luo, L.; Gonthier, Y. Chem. Eng. Sci. 2007, 62, 2096-2108.
51. Su, Y.; Zhao, Y.; Jiao, F.; Chen, G.; Yuan, Q. AIChE J. 2011, 57, 1409-1418.