Solarylations via 4-aminophenyl cations

Journal of Organic Chemistry

Volumn 75, Issue 4, 2010, Pages 1271-1276

  Dichiarante, Valentina ^a   Fagnoni, Maurizio ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CHEMICAL EQUATIONS; ENVIRONMENTALLY-FRIENDLY; GRAM SCALE; IMPACT ON THE ENVIRONMENT; METHYLSTYRENE; SOLAR IRRADIATION; TRAPPING AGENT; UV IRRADIATION;

COMPETITION; REACTION KINETICS; SOLAR RADIATION;

IRRADIATION;

4 CHLOROANILINE; ALPHA METHYLSTYRENE; AMINE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; CATION; HALIDE; WATER;

ARTICLE; ARYLATION; CATALYSIS; REACTION ANALYSIS; SOLAR RADIATION; SOLARYLATION; SUN EXPOSURE; ULTRAVIOLET IRRADIATION;

EID: 77249172173     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902669j     Document Type: Article

References (40)

1. Albini, A.; Fagnoni, M. Green Chem. 2004, 6, 1-6.
2. (a) Ciamician, G. Science 1912, 36, 385-394.
3. (b) Ciamician, G.; Silber, P. Ber. Dtsch. Chem. Ges. 1900, 33, 2911-2913.
4. Ciamician, G. Bull. Soc. Chim. Fr. 1908, 3 (4), i-xxxvi.
5. Albini, A.; Dichiarante, V. Photochem. Photobiol. Sci. 2009, 8, 248-254.
6. Protti, S.; Manzini, S.; Fagnoni, M.; Albini, A. The contribution of photochemistry to green chemistry. In Eco-Friendly Synthesis of Fine Chemicals; Ballini, R., Ed.; RSC Green Chemistry Series; Royal Society of Chemistry: Cambridge, UK, 2009; pp 80-111.
7. See, for example: (a) Stobbe, H. Liebigs Ann. Chem. 1908, 359, 1-48.
8. (b) Stobbe, H. Z. Elektrochem. 1908, 33, 473-483.
9. (c) Paternò, E.; Chieffi, G.; Perret, G. Gazz. Chim. Ital. 1914, 44, 151-164.
10. (d) Paternò, E.; Chieffi, G. Gazz. Chim. Ital. 1909, 39, 341-361.
11. Cian, C.-L.; Bochet, C. G. Chimia 2007, 61, 650-654.
12. Albini, A.; Fagnoni, M. The greenest reagent in organic synthesis: light. In Green Chemical Reactions; Tundo, P., Esposito, V., Eds.; Springer Science + Business Media B.V.: London, UK, 2008; pp 173-189.
13. (a) Protti, S.; Fagnoni, M. Photochem. Photobiol. Sci. 2009, 8, 1499-1516.
14. (b) Oelgemöller, M.; Jung, C.; Mattay, J. Pure Appl. Chem. 2007, 79, 1939-1947.
15. (c) Esser, P.; Pohlmann, B.; Scharf, H.-D. Angew. Chem., Int. Ed. 1994, 33, 2009-2023.
16. Dichiarante, V.; Fagnoni, M.; Albini, A. Photochemical arylation reactions. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, Germany, 2009; pp 513-535.
17. Protti, S.; Dondi, D.; Fagnoni, M.; Albini, A. Photochemistry for mild metal-free arylation reactions. In Experiments in green and sustainable chemistry; Roesky, H. W., Kennepohl, D. K., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2009; pp 260-265.
18. Rajan, S.; Muralimohan, K. Tetrahedron Lett. 1978, 5, 483-486.
19. Samoshin, A. V.; Samoshin, V. V. J. Undergrad. Chem. Res. 2006, 2, 13-16.
20. (a) Dichiarante, V.; Fagnoni, M. Synlett 2008, 787-800.
21. N1 reactions. In Handbook of Synthetic Photochemistry; Albini, A., Fagnoni, M., Eds.; Wiley-VCH: Weinheim, Germany, 2010; pp 319-352.
22. De Carolis, M.; Protti, S.; Fagnoni, M.; Albini, A. Angew. Chem., Int. Ed. 2005, 44, 1232-1236.
23. 2) causes a quite efficient hydrodehalogenation reaction via photo-generated phenyl cations (see ref 17). In a less H donating solvent such as MeCN this reduction occurs to some extent, depending on the concentration and type of nucleophile present in solution. Reduction of phenyl cations by hydrogen or electron transfer has been demonstrated by laser flash photolysis experiments (see refs 18 and 19).
24. Dichiarante, V.; Fagnoni, M.; Albini, A. Green Chem. 2009, 11, 942-945.
25. Guizzardi, B.; Mella, M.; Fagnoni, M.; Freccero, M.; Albini, A. J. Org. Chem. 2001, 66, 6353-6363.
26. Manet, I.; Monti, S.; Grabner, G.; Protti, S.; Dondi, D.; Dichiarante, V.; Fagnoni, M.; Albini, A. Chem. - Eur. J. 2008, 14, 1029-1039.
27. Similar vessels were recently used in solar photocatalyzed reactions. See: Protti, S.; Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Commun. 2009, 7351-7353.
28. Protti, S.; Dondi, D.; Fagnoni, M.; Albini, A. Green Chem. 2009, 11, 239-249.
29. 23 From the economical point of view, photochemical reactions via phenyl cations were more expensive, if compared with the corresponding metal-catalyzed reactions, and the main negative influence was due to the solvent (usually 2,2,2-trifluoroethanol).
30. Eissen, M.; Metzger, J. O. EATOS, Environmental Assessment Tool for Organic Syntheses, http://www.chemie.uni-oldenburg.de/oc/metzger/eatos/.
31. Lazzaroni, S.; Dondi, D.; Fagnoni, M.; Albini, A. J. Org. Chem. 2010, 75, 315-323.
32. Manet, I.; Monti, S.; Bortolus, P.; Fagnoni, M.; Albini, A. Chem. - Eur. J. 2005, 11, 4274-4282.
33. Lazzaroni, S.; Protti, S.; Fagnoni, M.; Albini, A. Org. Lett. 2009, 11, 349-352.
34. Fagnoni, M; Albini, A. Acc. Chem. Res. 2005, 38, 713-721.
35. Giumanini, A. G.; Chiavari, G.; Musiani, M. M.; Rossi, P. Synthesis 1980, 743-746.
36. Mikami, K.; Matsumoto, S.; Ishida, A.; Takamuku, S.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 1995, 117, 11134-11141.
37. Häfelinger, G.; Hack, F.; Westermayer, G. Chem. Ber. 1978, 111, 1323-1329.
38. Milanesi, S.; Fagnoni, M.; Albini, A. J. Org. Chem. 2005, 70, 603-610.
39. Fraboni, A.; Fagnoni, M.; Albini, A. J. Org. Chem. 2003, 68, 4886-4893.
40. Mella, M.; Coppo, P.; Guizzardi, B.; Fagnoni, M.; Freccero, M.; Albini, A. J. Org. Chem. 2001, 66, 6344-6352.