Computational study with DFT and kinetic models on the mechanism of photoinitiated aromatic perfluoroalkylations

Organic Letters

Volumn 17, Issue 11, 2015, Pages 2676-2679

  Fernández Alvarez, Victor M ^a   Nappi, Manuel ^a   Melchiorre, Paolo ^a,b   Maseras, Feliu ^a,c  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84982740759     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01069     Document Type: Article

References (33)

1. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176
2. Handbook of Synthetic Photochemistry; Albini, A.; Fagnoni, M. eds.; Wiley-VCH: Weinheim, 2010.
3. Balzani, V.; Credi, A.; Venturi, M. ChemSusChem 2008, 1, 26-58
4. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532
5. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
6. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
7. Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811-824
8. Foster, R. J. Phys. Chem. 1980, 84, 2135-2141
9. Rosokha, S. V.; Kochi, J. K. Acc. Chem. Res. 2008, 41, 641-653
10. Arceo, E. I.; Jurberg, D.; álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750-756
11. Arceo, E.; Bahamonde, A.; Bergonzini, G.; Melchiorre, P. Chem. Sci. 2014, 5, 2438-2442
12. Sameera, W. M. C.; Maseras, F. WIREs Comput. Mol. Sci. 2012, 2, 375-385
13. Domcke, W.; Sobolewski, A. L. Nat. Chem. 2013, 5, 257-258
14. Vela, S.; Mota, F.; Deumal, M.; Suizu, R.; Shuku, Y.; Mizuno, A.; Awaga, K.; Shiga, M.; Novoa, J. J.; Ribas-Arino, J. Nat. Commun. 2014, 5, 4411
15. Cox, N.; Retegan, M.; Neese, F.; Pantazis, D. A.; Boussac, A.; Lubitz, W. Science 2014, 345, 804-808
16. Laurent, A. D.; Adamo, C.; Jacquemin, D. Phys. Chem. Chem. Phys. 2014, 16, 14334-14356
17. Daniel, C. Coord. Chem. Rev. 2015, 282-283, 19-32
18. Fantacci, S.; De Angelis, F. Coord. Chem. Rev. 2011, 255, 2704-2726
19. Ma, J.; Su, T.; Li, M.-D.; Du, W.; Huang, J.; Guan, X.; Phillips, D. L. J. Am. Chem. Soc. 2012, 134, 14858-14868
20. Matt, B.; Xiang, X.; Kaledin, A. L.; Han, N.; Moussa, J.; Amouri, H.; Alves, S.; Hill, C. L.; Lian, T.; Musaev, D. G.; Izzet, G.; Proust, A. Chem. Sci. 2013, 4, 1737-1745
21. Nappi, M.; Bergonzini, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2014, 53, 4921-4925
22. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950-8958
23. For an example of a photo-induced HAS of electron-rich arenes with perfluoroalkyl radicals showing a quantum yield >200, see: Barata-Vallejo, S.; Martín Flesia, M.; Lantaño, B.; Argüello, J. E.; Peñéñory, A. B.; Postigo, A. Eur. J. Org. Chem. 2013, 998-1008
24. Balcells, D.; Maseras, F. New J. Chem. 2007, 31, 333-343
25. Fischer, H. Chem. Rev. 2001, 101, 3581-3610
26. Rush, L. E.; Pringle, P. G.; Harvey, J. N. Angew. Chem., Int. Ed. 2014, 53, 8672-8676
27. Goehry, C.; Besora, M.; Maseras, F. ACS Catal. 2015, 5, 2445-2451
28. Yang, T.; Parker, D. S. N.; Dangi, B. B.; Kaiser, R. I.; Stranges, D.; Su, Y.-H.; Chen, S.-Y.; Chang, A. H. H.; Mebel, A. M. J. Am. Chem. Soc. 2014, 136, 8387-8392
29. Wojnárovits, L.; Takács, E. Radiat. Phys. Chem. 2013, 87, 82-87
30. Elliot, A. J.; McCracken, D. R.; Buxton, G. V.; Wood, N. D. J. Chem. Soc. Faraday Trans. 1990, 86, 1539-1547
31. Morokuma, K. J. Chem. Phys. 1971, 55, 1236-1237
32. Bickelhaupt, F. M. J. Comput. Chem. 1999, 20, 114-128
33. Schoenebeck, F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2496-2497