A spectroscopic and computational study of a photoinduced cross-dehydrogenative coupling reaction of a stable semiquinone radical

Chemistry - A European Journal

Volumn 18, Issue 43, 2012, Pages 13605-13608

  Grilj, Jakob ^a   Todorova, Tanya Kumanova ^b   Yi, Chenyi ^c   Liu, Shi Xia ^c   Vauthey, Eric ^a   Decurtins, Silvio ^c  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b EPFL   (Switzerland)

^c UNIVERSITY OF BERN   (Switzerland)

Author keywords

density functional calculations; photochemistry; radicals; transient absorption; transition states

Indexed keywords

ABSORPTION SPECTROSCOPY; DENSITY FUNCTIONAL THEORY; PHOTOCHEMICAL REACTIONS; REACTION INTERMEDIATES;

COMPUTATIONAL STUDIES; CROSS DEHYDROGENATIVE COUPLINGS; RADICALS; SEMIQUINONE RADICALS; TRANSIENT ABSORPTION; TRANSIENT ABSORPTION SPECTROSCOPIES; TRANSITION STATE; TYPE-II PHOTOREACTION;

CYCLIZATION;

EID: 84961974326     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201463     Document Type: Article

References (36)

1. J. C. Scaiano, in CRC Handbook of Organic Photochemistry, CRC Press, Boca Raton, 1987.
2. D. H. R. Barton, J. M. Beaton, L. E. Geller, M. M. Pechet, J. Am. Chem. Soc. 1960, 82, 2640-2641
3. M. Akhtar, M. M. Pechet, J. Am. Chem. Soc. 1964, 86, 265-268.
4. M. Rosenberg, T. I. SÃlling, Chem. Phys. Lett. 2010, 484, 113-118
5. A. Sugimoto, T. Fukuyama, Y. Sumino, M. Takagi, I. Ryu, Tetrahedron 2009, 65, 1593-1598.
6. P. J. Wagner, B. S. Park, in Organic Photochemistry, Vol. 11, (Ed.:, A. Pawda,), Marcel Dekker, New York, 1991, Chapter 4
7. P. J. Wagner, in CRC Handbook of Organic Photochemistry and Photobiology, CRC Press, Boca Raton, 1995.
8. L. Shen, W.-H. Fang, J. Org. Chem. 2011, 76, 773-779
9. L. Ding, L. Shen, X.-B. Chen, W.-H. Fang, J. Org. Chem. 2009, 74, 8956-8962
10. J. N. Moorthy, S. Samanta, A. L. Koner, S. Saha, W. M. Nau, J. Am. Chem. Soc. 2008, 130, 13608-13617
11. D. Álvarez-Dorta, E. I. Leõn, A. R. Kennedy, C. Riesco-Fagundo, E. Suárez, Angew. Chem. 2008, 120, 9049-9051
12. Angew. Chem. Int. Ed. 2008, 47, 8917-8919
13. X. Cai, P. Cygon, B. Goldfuss, A. G. Griesbeck, H. Heckroth, M. Fujitsuka, T. Majima, Chem. Eur. J. 2006, 12, 4662-4667
14. D. Braga, S. Chen, H. Filson, L. Maini, M. R. Netherton, B. O. Patrick, J. R. Scheffer, C. Scott, W. Xia, J. Am. Chem. Soc. 2004, 126, 3511-3520.
15. C. Yi, C. Blum, S.-X. Liu, T. D. Keene, G. Frei, A. Neels, S. Decurtins, Org. Lett. 2009, 11, 2261-2264.
16. C. Yi, S.-X. Liu, A. Neels, P. Renaud, S. Decurtins, Org. Lett. 2009, 11, 5530-5533.
17. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654-2672
18. J. A. Ellman, Science 2007, 316, 1131-1132
19. M. P. Doyle, K. I. Goldberg, Acc. Chem. Res. 2012, 45, 777-777.
20. Y. Du, J. Xue, M.-D. Li, X. Guan, D. W. McCamant, D. L. Phillips, Chem. Eur. J. 2010, 16, 6961-6972.
21. I. H. M. van Stokkum, D. L. Larsen, R. van Grondelle, Biochim. Biophys. Acta Bioenerg. 2004, 1657, 82-104.
22. S. A. Kovalenko, A. L. Dobryakov, J. Ruthmann, N. P. Ernsting, Phys. Rev. A 1999, 59, 2369-2384.
23. T. Polívka, V. Sundström, Chem. Phys. Lett. 2009, 477, 1-11.
24. V. V. Yanshole, P. S. Sherin, N. P. Gritsan, O. A. Snytnikova, V. I. Mamatyuk, J. Grilj, E. Vauthey, R. Z. Sagdeev, Y. P. Tsentalovich, Phys. Chem. Chem. Phys. 2010, 12, 9502-9515.
25. N. Banerji, G. Duvanel, A. Perez-Velasco, S. Maity, N. Sakai, S. Matile, E. Vauthey, J. Phys. Chem. A 2009, 113, 8202-8212.
26. J. Grilj, E. N. Laricheva, M. Olivucci, E. Vauthey, Angew. Chem. 2011, 123, 4589-4591
27. Angew. Chem. Int. Ed. 2011, 50, 4496-4498.
28. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868
29. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158-6170.
30. T. H. Dunning, J. Chem. Phys. 1989, 90, 1007-1023.
31. Gaussian 09, Revision A.1, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ã. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
32. S. Miertuš, E. Scrocco, J. Tomasi, Chem. Phys. 1981, 55, 117-129.
33. C. J. Cramer, in Essentials of Computational Chemistry, 2 nd ed., Wiley, Chichester, UK, 2004.
34. E. Runge, E. K. U. Gross, Phys. Rev. Lett. 1984, 52, 997-1000
35. E. K. U. Gross, W. Kohn, Phys. Rev. Lett. 1985, 55, 2850-2852.
36. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.