Photoactivation of (p-methoxyphenyl)(trifluoromethyl)diazirine in the presence of phenolic reaction partners

Chemistry - A European Journal

Volumn 19, Issue 21, 2013, Pages 6551-6555

  Raimer, Björn ^a   Lindel, Thomas ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

carbenes; density functional calculation; diazirines; photoaffinity labeling; photochemistry

Indexed keywords

CARBENES; CHEMICAL BIOLOGY; DIAZIRINES; EQUI-MOLAR SOLUTION; FRIEDEL-CRAFTS ALKYLATION; PHOTO ACTIVATIONS; PHOTOAFFINITY LABELING; REACTION PARTNERS;

DENSITY FUNCTIONAL THEORY; PHOTOCHEMICAL REACTIONS;

AMINO ACIDS;

3 (4 METHOXYPHENYL) 3 (TRIFLUOROMETHYL) 3H DIAZIRINE; 3-(4-METHOXYPHENYL)-3-(TRIFLUOROMETHYL)-3H-DIAZIRINE; AZIRINE DERIVATIVE; DIAZOMETHANE; DRUG DERIVATIVE; PHENOL DERIVATIVE; TYROSINE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; RADIATION EXPOSURE;

ALKYLATION; AZIRINES; CATALYSIS; DIAZOMETHANE; MOLECULAR STRUCTURE; PHENOLS; PHOTOCHEMICAL PROCESSES; TYROSINE;

EID: 84877760840     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203479     Document Type: Article

References (36)

1. A. Blencowe, W. Hayes, Soft Matter 2005, 1, 178-205
2. J. Das, Chem. Rev. 2011, 111, 4405-4417
3. L. Dubinsky, B. P. Krom, M. M. Meijler, Bioorg. Med. Chem. 2012, 20, 554-570
4. F. Kotzyba-Hibert, I. Kapfer, M. Goeldner, Angew. Chem. 1995, 107, 1391-1408
5. Angew. Chem. Int. Ed. Engl. 1995, 34, 1296-1312.
6. U. K. Shigdel, J. Zhang, C. He, Angew. Chem. 2008, 120, 96-99
7. Angew. Chem. Int. Ed. 2008, 47, 90-93
8. M. Winnacker, S. Breeger, R. Strasser, T. Carell, ChemBioChem 2009, 10, 109-118.
9. J. Brunner, H. Senn, F. M. Richards, J. Biol. Chem. 1980, 255, 3313-3318.
10. Review on valence isomerization between diazo compounds and diazirines:, S. M. Korneev, Eur. J. Org. Chem. 2011, 6153-6175.
11. Y. Hatanaka, M. Hashimoto, H. Nakayama, Y. Kanaoka, Chem. Pharm. Bull. 1994, 42, 826-831
12. M. Hashimoto, Y. Hatanaka, Chem. Pharm. Bull. 2005, 53, 1510-1512.
13. M. Daghish, L. Hennig, M. Findeisen, S. Giesa, F. Schumer, H. Hennig, A. G. Beck-Sickinger, P. Welzel, Angew. Chem. 2002, 114, 2404-2408
14. Angew. Chem. Int. Ed. 2002, 41, 2293-2297.
15. T. Mayer, M. E. Maier, Eur. J. Org. Chem. 2007, 4711-4720.
16. S. Kosemura, H. Emori, S. Yamamura, T. Anai, K. Tomita, K. Hasegawa, Tetrahedron Lett. 1997, 38, 2125-2128.
17. T. Hosoya, T. Hiramatsu, T. Ikemoto, M. Nakanishi, H. Aoyama, A. Hosoya, T. Iwata, K. Maruyama, M. Endo, M. Suzuki, Org. Biomol. Chem. 2004, 2, 637-641
18. T. Hiramatsu, Y. Guo, T. Hosoya, Org. Biomol. Chem. 2007, 5, 2916-2919.
19. G.-L. Chee, J. C. Yalowich, A. Bodner, X. Wu, B. B. Hasinoff, Bioorg. Med. Chem. 2010, 18, 830-838.
20. N. Kanoh, T. Nakamura, K. Honda, H. Yamakoshi, Y. Iwabuchi, H. Osada, Tetrahedron 2008, 64, 5692-5698.
21. H. Ismaili, S. Lee, M. S. Workentin, Langmuir 2010, 26, 14958-14964.
22. T. K. Lindhorst, M. Märten, A. Fuchs, S. D. Knight, Beilstein J. Org. Chem. 2010, 6, 810-822.
23. B3LYP/6-31G(d) has recently been used by Platz and co-workers for (p-methoxyphenyl)carbene., Y. Zhang, G. Burdzinski, J. Kubicki, S. Vyas, C. M. Hadad, M. Sliwa, O. Poizat, G. Buntinx, M. S. Platz, J. Am. Chem. Soc. 2009, 131, 13784-13790.
24. 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, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
25. -1, see
26. M.-G. Song, R. S. Sheridan, J. Phys. Org. Chem. 2011, 24, 889-893.
27. M.-G. Song, R. S. Sheridan, J. Am. Chem. Soc. 2011, 133, 19688-19690.
28. J. Wang, J. Kubicki, T. L. Gustafson, M. S. Platz, J. Am. Chem. Soc. 2008, 130, 2304-2313.
29. Y. Hatanaka, M. Hashimoto, H. Kurihara, H. Nakayama, Y. Kanaoka, J. Org. Chem. 1994, 59, 383-387.
30. M. T. H. Liu, K. Ramakrishnan, Tetrahedron Lett. 1977, 18, 3139-3142.
31. J. Wang, J. Kubicki, H. Peng, M. S. Platz, J. Am. Chem. Soc. 2008, 130, 6604-6609.
32. G. Diderich, Helv. Chim. Acta 1972, 55, 2103-2112; on purification of diazo compound 7 by fast chromatography on silica gel, the deep-red color faded quickly. NMR spectra had to be taken immediately after purification.
33. Y. Zhang, S. Vyas, C. M. Hadad, M. S. Platz, J. Phys. Chem. A 2010, 114, 5902-5912.
34. W. Kirmse, Sci. Isr.-Technol. Advantages Advances in Carbene Chemistry 2001, 3, 1-51.
35. W. Kirmse, W. Kilian, S. Steenken, J. Am. Chem. Soc. 1990, 112, 6399-6400.
36. M. Wiegand, T. K. Lindhorst, Eur. J. Org. Chem. 2006, 4841-4851.