Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide

Chemical Reviews

Volumn 107, Issue 9, 2007, Pages 3800-3842

  Recupero, Francesco ^a   Punta, Carlo ^a  

^a POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL BONDS; ORGANIC COMPOUNDS; PHYSICAL CHEMISTRY; SYNTHESIS (CHEMICAL);

N-HYDROXYPHTHALIMIDE; PEROXYL RADICAL;

FREE RADICAL REACTIONS;

EID: 35148843206     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr040170k     Document Type: Review

References (221)

1. Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233.
2. Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, 2005.
3. Walling, C. In Active Oxygen in Chemistry; Foote, C. S., Valentie, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: Glasgow, 1995; p 24.
4. Suresh, A. K.; Sharma, M. M.; Sridhar, T. Ind. Eng. Chem. Res. 2000, 39, 3958.
5. Salem, L. Electrons in Chemical Reactions. First Principles; Wiley-Interscience: New York, 1982.
6. Simandi, L. L., Ed. Dioxygen Activation and Homogeneous Catalytic Oxidation; Elsevier: Amsterdam, 1991. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992. Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds. The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Plenum: New York, 1993. Sheldon, R. A.; Kochi, J. K. Metal-catalyzed Oxidations of Organic Compounds; Academic: New York, 1981.
7. Bäckvall, J.-E., Eds. Modern Oxidation Methods; Wiley-VCH: Weinheim, 2004.
8. Centi, G.; Trifirò, F.; Cavani, F. Selective Oxidation by Heterogeneous Catalysis; Kluwer Academic/Plenum: New York, 2001. Sheldon, R. A., van Bekkum, H., Eds. Fine Chemicals through Heterogeneous Catalysis; Wiley-VCH: Weinheim, 2001.
9. Schreiner, P. R.; Fokin, A. A. Chem. Rec. 2004, 3, 247.
10. Fokin, A. A.; Schreiner, P. R. Adv. Synth. Catal. 2003, 345, 1035.
11. Fokin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551.
12. Sheldon, R. A. J. Chem. Technol. Biotechnol. 1997, 68, 381.
13. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329.
14. Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947.
15. Adam, W.; Saha-Möller, C. R.; Ganeshpure, P. A. Chem. Rev. 2001, 101, 3499.
16. Ishii, Y.; Sakaguchi, S. Catal. Surv. Jpn. 1999, 3, 27.
17. Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393.
18. Gambarotti, C.; Punta, C.; Recupero, F. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: Weinheim, 2005; http:// dx.doi.org/10.1002/047084289X.rn00598.
19. Minisci, F.; Recupero, F.; Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A 2003, 63, 204.
20. Minisci, F.; Punta, C.; Recupero, F. J. Mol. Catal. A 2006, 251, 129.
21. Ishii, Y.; Sakaguchi S. In Modern Oxidation Methods; Bäckvall, J.-E., Eds.; Wiley-VCH: New York, 2004; p 119.
22. Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth. Catal. 2004, 346, 1051.
23. Karakurt, A.; Dalkara, S.; Ozalp, M.; Ozbey, S.; Kendi, E.; Stables, J. P. Eur. J. Med. Chem. 2001, 36, 421.
24. Grochowski, E.; Boleslawska, T.; Jurczak, J. Synthesis 1977, 718.
25. Masui, M.; Ueshima, T.; Ozaki, S. Chem. Commun. 1983, 479.
26. Masui, M.; Hara, S.; Ueshima, T.; Kawaguchi, T.; Ozaki, S. Chem. Pharm. Bull. 1983, 31, 4209.
27. Masui, M.; Rosomi, K.; Tsuchida, K.; Ozaki, S. Chem. Pharm. Bull. 1985, 33, 4798.
28. Masui, M.; Hara, S.; Ozaki, S. Chem. Pharm. Bull. 1986, 34, 975.
29. Masui, M.; Kawaguchi, T.; Ozaki, S. Chem. Commun. 1985, 1484.
30. Masui, M.; Kawaguchi, T.; Yoshida, S.; Ozaki, S. Chem. Pharm. Bull. 1986, 34, 1837.
31. Foricher, J.; Furbringer, C.; Pfoertner, K. EP Patent 0198351, 1986.
32. Foricher, J.; Furbringer, C.; Pfoertner, K. U.S. Patent 5,030,739, 1991.
33. Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934.
34. Focus on Catalysts, 2004, Issue 1, January 2004, p 7.
35. The Minister of Education, Culture, Sports, Science and Technology of Japan in 2003 awarded "The Third Green and Sustainable Chemistry Award" to Prof. Ishii and the Daicel Chemical Company for their efforts relevant to the development of NHPI based industrial processes with low environmental impact.
36. Koshino, N.; Saha, B.; Espenson, J. H. J. Org. Chem. 2003, 68, 9364.
37. Ueda, C.; Noyama, M.; Ohmori, H.; Masui, M. Chem. Pharm. Bull. 1987, 35, 1372.
38. Cai, Y.; Koshino, N.; Saha, B.; Espenson, J. H. J. Org. Chem. 2005, 70, 238.
39. Lemaire, H.; Rassat, A. Tetrahedron Lett. 1964, 2245.
40. Mackor, A.; Wajer, Th. A. J. W.; De Boer, T. Tetrahedron 1968, 24, 4542.
41. Amorati, R.; Lucarini, M.; Mugnaini, M.; Pedulli, G. F.; Minisci, F.; Recupero, F.; Fontana, F.; Astolfi, P.; Greci, L. J. Org. Chem. 2003, 68, 1747.
42. Malatesta, V.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 3094.
43. Jenkins, T. C.; Perkins, M. J.; Siew, N. P. Y. J. Chem. Soc., Chem. Commun. 1975, 880.
44. Aurich, H. G. In The Chemistry of Amino, Nitroso, Nitro Compounds and of their Derivatives; Patai, S., Ed.; Wiley: Chichester, 1982; Chapter 14.
45. Chatgilialogu, C.; Malatesta, V.; Ingold, K. U. J. Phys. Chem. 1980, 84, 3597.
46. Gorgy, K.; Lepretre, J.-C.; Saint-Aman, E.; Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.-L. Electrochim. Acta 1998, 44, 385.
47. Annunziatini, C.; Baiocco, P.; Gerini, M. F.; Lanzalunga, O.; Sjögren, B. J. Mol. Catal. B: Enzym. 2005, 32, 89.
48. Koshino, N.; Cai, Y.; Espenson, J. H. J. Phys. Chem. A 2003, 107, 4262.
49. Bordwell, F. G.; Liu, W.-Z. J. Am. Chem. Soc. 1996, 118, 10819.
50. Annunziatini, C.; Gerini, M. F.; Lanzalunga, O.; Lucarini, M. J. Org. Chem. 2004, 69, 3431.
51. Hussain, S. A.; Jenkins, T. C.; Perkins, M. J. Tetrahedron Lett. 1977, 36, 3199.
52. Cohen, A. D.; Zeng, B.-B.; King, B. S.; Toscano, J. P. J. Am. Chem. Soc. 2003, 125, 1444.
53. Baciocchi, E.; Gerini, M. F.; Lanzalunga, O. J. Org Chem. 2004, 69, 8963.
54. Minisci, F.; Punta, C.; Recupero, F.; Fontana, F.; Pedulli, G. F. Chem. Commun. 2002, 7, 688.
55. Coseri, S.; Mendenhall, G. D.; Ingold, K. U. J. Org. Chem. 2005, 70, 4629.
56. Mihailović, M. Lj.; Čeković, Ž.; Lorenc, Lj. Oxidations with Lead Tetraacetate. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., De Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; p 758.
57. Mahoney, L. R.; DaRooge, M. A. J. Am. Chem. Soc. 1970, 92, 4063.
58. Russell, G. A.; Williamson, R. C. J. Am. Chem. Soc. 1964, 86, 2357.
59. Pratt, D. A.; DiLabio, G. A.; Mulder, P.; Ingold, K. U. Acc. Chem. Res. 2004, 37, 334.
60. Avila, D. V.; Ingold, K. U.; Lusztyk, J.; Green, W. H.; Procopio, D. R. J. Am. Chem. Soc. 1995, 117, 2929.
61. Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469.
62. Shaik, S.; de Visser, P. S.; Wu, W.; Song, L.; Hiberty, P. C. J. Phys. Chem. A 2002, 106, 5043.
63. Howard, J. A. In Peroxyl Radicals; Alfassi, Z., Ed.; Wiley & Sons: Chichester, 1997.
64. Marchai, A.; Douglas, G. K.; Bakac, A.; Espenson, J. H. J. Phys. Chem. A 1991, 95, 4440.
65. Howard, J. A. In Free Radicals; Kochi, J. K., Ed.; Wiley & Sons: New York, 1973; Volume 2, Charter 12.
66. Howard, J. A.; Scaiano, J. In Landolt Börnstein Numerical Data and Functional Reactions in Science and Technology; Fischer, H., Ed.; Sprinter-Verlag: Berlin, 1984; Volume 3, Subvolume d.
67. Ingold, K. U. Acc. Chem. Res. 1969, 2, 1.
68. Lucarini, M.; Pedulli, G. F.; Valgimigli L. J. Org. Chem. 1998, 63, 4497.
69. Hermans, I.; Vereecken, L.; Jacobs, P. A.; Peeters, J. Chem. Commun. 2004, 1140.
70. Thomas, J. R. J. Am. Chem. Soc. 1967, 89, 4872.
71. Bottle, S. E.; Chand, U.; Micallef, A. S. Chem. Lett. 1997, 857.
72. Johnston, L. J.; Tencer, M.; Scaiano, J. C. J. Org. Chem. 1986, 51, 2806.
73. Matsui, S.; Fujita, T. Catal. Today 2001, 71, 145.
74. Matyjaszewski, K., Davis, T. P., Eds. Handbook of Radical Polymerization; John Wiley & Sons: New York, 2002.
75. Cornejo, J. J.; Larson, K. D.; Mendenhall, G. D. J. Org. Chem. 1985, 50, 5382.
76. Hermans, I.; Nguyen, T. L.; Jacobs, P. A.; Peeters, J. ChemPhysChem 2005, 6, 637.
77. Ravens, D. A. S. Trans. Faraday Soc. 1959, 55, 1768.
78. Kamiya, Y.; Nakajima, T.; Sakoda, K. Bull. Chem. Soc. Jpn. 1966, 39, 519.
79. Shimizu, A.; Tanaka, K.; Ogawa, H.; Matsuoka, Y.; Fujimori, M.; Nagamori, Y.; Hamachi, H.; Rimura, K. Bull. Chem. Soc. Jpn. 2003, 76, 1993.
80. Wang, J.-R.; Liu, L.; Wang, Y.-F.; Zhang, Y.; Deng, W.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 4647.
81. Sawatari, N.; Yokota, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2001, 66, 7889.
82. Baucherel, X.; Gonsalvi, L.; Arends, I. W. C. E.; Ellwood, S.; Sheldon, R. A. Adv. Synth. Catal. 2004, 346, 286.
83. Tong, X.; Xu, J.; Miao, H. Adv. Synth. Catal. 2005, 347, 1953.
84. Dobies, O.; Benson, S. W. J. Phys. Chem. A 1997, 101, 6030.
85. Shibamoto, A.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2002, 43, 8859.
86. Sakaguchi, S.; Kato, S.; Iwahama, T.; Ishii, Y. Bull. Chem. Soc. Jpn. 1998, 71, 1240.
87. Finn, M.; Friedline, R.; Suleman, N. K.; Wohl, C. J.; Tanko, J. M. J. Am. Chem. Soc. 2004, 126, 7578.
88. Holmes, J. L. Int. J. Mass Spectrom. Ion Processes 1992, 118-119, 381.
89. Recupero, F.; Bravo, A.; Bjørsvik, H.-R.; Fontana, F.; Minisci, F.; Piredda, M. J. Chem. Soc., Perkin Trans. 2 1997, 2399.
90. Ishii, Y.; Kato, S.; Iwahama, T.; Sakaguchi, S. Tetrahedron Lett. 1996, 37, 4993.
91. Minisci, F.; Fontana, F.; Zhao, L. H.; Banfi, S.; Quici, S. Tetrahedron Lett. 1994, 35, 8033.
92. Matsunaka, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1999, 40, 2165.
93. Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
94. Tashiro, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2001, 343, 220.
95. Saba, B.; Koshino, N.; Espenson, J. H. J. Phys. Chem. A 2004, 108, 425.
96. Partenheimer, W. Catal. Today 1995, 25, 69.
97. Shibamoto, A.; Sakaguchi, S.; Ishii, Y. Org. Process Res. Dev. 2000, 4, 505.
98. Michael, J. P. Nat. Prod. Rep. 1997, 14, 605.
99. Jones, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 5, pp 167.
100. Cain, C. K.; Planpin, J. N.; Sam, J. J. Org. Chem. 1955, 20, 466.
101. Ladner, D.W. Synth. Commun. 1986, 16, 157.
102. Sakaguchi, S.; Shimamoto, A.; Ishii, Y. Chem. Commun. 2002, 180.
103. Fritz-Langhals, E.; Kunath, B. Tetrahedron Lett. 1998, 39, 5955.
104. Rajabi, F.; Clark, J. H.; Karimi, B.; Macquarrie, D. J. Org. Biomol. Chem. 2005, 3, 725.
105. Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.-L. Chem. Commun. 1997, 447.
106. Einhorn, C.; Einhorn, J.; Marcadal, C.; Pierre, J.-L. J. Org. Chem. 1999, 64, 4542.
107. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
108. Cho, S.-H.; Cheong, M.-S.; Jung, K.-D.; Kim, C.-S.; Han, S.-H. Appl. Catal. A: Gen. 2004, 267, 241.
109. Yang, G.; Ma, Y.; Xu, J. J. Am. Chem. Soc. 2004, 126, 10542.
110. Yang, G.; Zhang, Q.; Miao, H.; Tong, X.; Xu, J. Org. Lett. 2005, 7, 263.
111. Minisci, F.; Recupero, F.; Gambarotti, C.; Punta, C.; Paganelli, R. Tetrahedron Lett. 2003, 44, 6919.
112. Schmieder-van de Vondervoort, L.; Bouttemy, S.; Heu, F.; Weissenbock, K.; Alsters, P. L. Eur. J. Org. Chem. 2003, 3, 578.
113. Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.; Feiters, M. C.; Nolte, R. J. M. Tetrahedron 2000, 7797.
114. Patai, S., Ed. Chemistry of Peroxides; Wiley-Interscience: New York 1983.
115. Hock, H.; Lang, B. Chem. Ber. 1944, 77, 257.
116. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520.
117. (a) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1593.
118. (b) Walling, C.; Wagner, P. I. J. Am. Chem. Soc. 1964, 86, 3368.
119. Minisci, F.; Recupero, F.; Cecchetto, A.; Gambarotti, C.; Punta, C.; Paganelli, R. Org. Process Res. Dev. 2004, 8, 163.
120. Boger, D. L.; Coleman, R. S. J. Org. Chem. 1986, 51, 5436.
121. Volyi, I.; Janssen, A. G.; Mark, H. J. Phys. Chem. 1945, 49, 461.
122. Aoki, Y.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2004, 346, 199.
123. Aoki, Y.; Hirai, N.; Sakaguchi, S.; Ishii, Y. Tetrahedron 2005, 61, 10995.
124. Arends, I. W. C. E.; Sasidharan, M.; Kühnle, A.; Duda, M.; Jost, C.; Sheldon, R. A. Tetrahedron 2002, 58, 9055.
125. Jordan, W.; Barneveld, H.; van Gerlich, O.; Kleine-Boymann, M.; Ullrich, J. Ullmann's Encyclopedia of Industrial Chemistry; VCH: Weinheim, 1991; Vol. A19, p 307.
126. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley-Interscience Publications: New York, 2001; pp 1514.
127. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
128. Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502.
129. Oakley, M. A.; Woodward, S.; Coupland, K.; Parker, D.; Temple-Heald, C. J. Mol. Catal. A 1999, 150, 105.
130. Brandi, P.; Galli, C.; Gentili, P. J. Org. Chem. 2005, 70, 9521.
131. Denisov, E. T.; Denisova, T. Handbook of Antioxidants: Bond Association Energies, Rate Constants, Activation Energies, and Enthalpies of Reactions; CRC Press: Boca Raton, FL, 2000.
132. Denisov, E. T.; Khursan, S. L. Russ. J. Phys. Chem. 2000, 74, Suppl 3, S491.
133. Minisci, F.; Recupero, F.; Ceechetto, A.; Gambarotti, C.; Punta, C.; Faletti, R.; Paganelli, R.; Pedulli, G. F. Eur. J. Org. Chem. 2004, 109.
134. Viche, H. G.; Janausek, Z.; Mereny, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148.
135. Baiocco, P.; Barreca, A. M.; Fabbrini, M.; Galli, C.; Gentili, P. Org. Biomol. Chem. 2003, 1, 191.
136. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
137. Amati, A.; Dosualdo, G.; Fontana, F.; Minisci, F.; Bjørsvik, H.-R. Org. Process Res. Dev. 1998, 2, 261.
138. Figiel, P. J.; Sobczak, J. M.; Ziolkowski, J. J. Chem. Commun. 2004, 244.
139. Figiel, P. J.; Sobczak, J. M. Pol. J. Chem. 2001, 75, 869.
140. Kim, S. S.; Rajagopal, G. Synth. Commun. 2004, 34, 2237.
141. Astolfi, P.; Brandi, P.; Galli, C.; Gentili, P.; Gerini, M. F.; Greci, L.; Lanzalunga, O. New J. Chem. 2005, 29, 1308.
142. Messerschmidt, A. Multi-Copper Oxidases; World Scientific: Singapore, 1997.
143. Cantarella, G.; Galli, C.; Gentili, P. New J. Chem. 2004, 28, 366.
144. Fukuda, O.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2001, 42, 3479.
145. Mokaya, R.; Poliakoff, M, Nature 2005, 437, 1243.
146. Walling, C.; Clark, R. T. J. Am. Chem. Soc. 1974, 96, 4530.
147. Van Sickle, D. E.; Mayo, F. R.; Arluck, R. M. J. Am. Chem. Soc. 1965, 87, 4824.
148. Mayo, F. R. Acc. Chem. Res. 1968, 1, 193.
149. Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama Nishiyama, Y. J. Org. Chem. 1996, 61, 4520.
150. Ozaki, S.; Hamaguci, T.; Tsuchida, K.; Kimata, Y.; Masui, M. J. Chem. Soc., Perkin Trans. 2 1989, 951.
151. Hara, T.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2001, 66, 6425.
152. Punta, C.; Rector, C. L.; Porter, N. A. Chem. Res. Toxicol. 2005, 18, 349.
153. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 1999, 727.
154. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Heterocycles 2000, 52, 693.
155. Iwahama, T.; Hatta, G.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 163.
156. J_sorgensen,K. A. Chem. Rev. 1989, 89, 431.
157. Minisci, F.; Gambarotti, C.; Pierini, M.; Porta, O.; Punta, C.; Recupero, F.; Lucarini, M.; Veronica, M. Tetrahedron Lett. 2006, 47, 1421.
158. Utimoto, K.; Miwa, M.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277.
159. Smith, A. B., III; Levenberg, P. A.; Suits, J. Z. Synthesis 1986, 184.
160. Karpf, M.; Huguet, J.; Dreiding, A. S. Helv. Chim. Acta 1986, 65, 13.
161. Tam, S. T.-K.; Klein, R. S.; De Las Heras, F. G.; Fox, J. J. J. Org. Chem. 1979, 44, 4854.
162. Sayo, N.; Azuma, K.-I.; Mikawa, K.; Nakai, T. Tetrahedron Lett. 1984, 25, 565.
163. Jargstorff, C.; Wille, U. Eur. J. Org. Chem. 2003, 3173.
164. Eikawa, M.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1999, 64, 4676.
165. d'Acunzo, F.; Baiocco, P.; Galli, C. New J. Chem. 2003, 27, 329.
166. Karimi, B.; Rajabi, J. Org. Lett. 2004, 6, 2841.
167. Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2000, 65, 6502.
168. Chen, Y.; Wang, G. Tetrahedron Lett. 2001, 42, 4955.
169. Karimi, B.; Rajabi, J. Synthesis 2003, 15, 2373.
170. Burkey, T. J.; Castelhano, A. L.; Griller, D.; Lossing, F. P. J. Am. Chem. Soc. 1983, 105, 4701.
171. Cecchetto, A.; Minisci, F.; Recupero, F.; Fontana, F.; Pedulli, G. F. Tetrahedron Lett. 2002, 43, 3605.
172. Baciocchi, E.; Bietti, M.; Gerini, M. F.; Lanzalunga, O. J. Org. Chem. 2005, 70, 5144.
173. Minisci, F.; Punta, C.; Recupero, F.; Fontana, F.; Pedulli, G. F. J. Org. Chem. 2002, 67, 2671.
174. Wang, J.-R.; Liu, L.; Wang, Y.-F.; Zhang, Y.; Deng, W.; Guo, Q.- X. Tetrahedron Lett. 2005, 46, 4647.
175. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 9059.
176. Kanabus-Kaminska, J. M.; Hawari, J. A.; Griller, D.; Chatgilialoglu, C. J. Am. Chem. Soc. 1987, 109, 5267.
177. Minisci, F.; Recupero, F.; Punta, C.; Guidarini, C.; Fontana, F.; Pedulli, G. F. Synth. Lett. 2002, 7, 1173.
178. Tayama, O.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Eur. J. Org. Chem. 2003, 2286.
179. Minisci, F.; Porta, O.; Recupero, F.; Gambarotti, C.; Paganelli, R.; Pedulli, G. F.; Fontana, F. Tetrahedron Lett. 2004, 45, 1607.
180. Singh, H.; Tedder, J. M. J. Chem. Soc. B 1964, 4737.
181. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
182. Albright, L. F. Chem. Eng. 1966, 73, 149. Markofsky, S. B. In Ullman's Encyclopedia of Industrial Organic Chemicals; Elvers, B., Hawkins, S., Eds.; Wiley-VCH: Weinheim, 1999; Vol. 6, pp 3487.
183. Albright, L. F. In Kirk-Othmer Encyclopedia of Chemical Technology; Kroschwite, J. I., Howe-Grant, M., Eds.; Wiley-VCH: New York, 1995; Vol. 17, pp 68.
184. Ishii, Y.; Sakaguchi, S.; Nishiwaki, Y.; Kitamura, T. Angew. Chem., Int. Ed. 2001, 40, 222.
185. Sawatari, N.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 2053.
186. Sakaguchi, S.; Eikawa, M.; Ishii, Y. Tetrahedron Lett. 1997, 38, 7075.
187. Eikawa, M.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1999, 64, 4676.
188. Sakaguchi, S.; Hirabayashi, T.; Ishii, Y. Chem. Commun. 2002, 516.
189. Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. Angew. Chem., Int. Ed. 2004, 43, 1120.
190. Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry, 4th ed.; Wiley-VCH: Weinheim, 2003.
191. Giese, B. In Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, 1986.
192. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 715.
193. Motherwell, W. B.; Crich, D. Free-Radical Reactions in Organic Synthesis; Academic Press: London, 1992.
194. Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Synthesis; Wiley: Chichester, 1995. Parsons, A. F. An Introduction to Free Radical Chemistry; Blackwell Science: Oxford, 2000.
195. Chatgilialoglu, C.; Renaud, P. In General Aspects of the Chemistry of Radicals; Alfassi, Z. B., Eds.; Wiley: Chichester, 1999.
196. Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001.
197. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
198. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194.
199. Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222.
200. Hara, T.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2001, 66, 6425.
201. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 613.
202. Munoz, H.; Tamariz, J.; Jiminez, R.; Mora, G. G. J. Chem. Res. (S) 1993, 68.
203. Laurent-Robert, H.; Le Roux, C.; Dubac, J. Synlett 1998, 1138.
204. Li, S.; Vert, M. In Degradable Polymers; Scott, G., Gilead, D., Eds.; Chapman & Hall: London; 1995; pp 43.
205. Puthuraya, K.; Oomura, Y.; Shimizu, N. Brain Res. 1985, 332, 165.
206. Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
207. Kagayama, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2005, 46, 3687.
208. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
209. Punniyamurthy, T.; Bhatia, B.; Iqbal, J. J. Org. Chem. 1994, 59, 850.
210. Braun, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 24.
211. Hirano, K.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2002, 43, 3617.
212. Tsujimoto, S.; Iwahanna, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 2352.
213. Kharasch, M. S.; Urry, W. H.; Kuderna, B. M. J. Org. Chem. 1949, 14, 239.
214. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
215. Tsujimoto, S.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 5601.
216. Minisci, F. Synthesis 1973, 1. Minisci, F. Top. Curr. Chem. 1976, 62, 1.
217. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489.
218. Minisci, F.; Vismara, E.; Fontana, F. J. Heterocycl. Chem. 1990, 27, 79.
219. Porta, O.; Minisci, F. In Handbook of C-H transformation; Dyker, G., Ed.; Wiley-VCH: New York, 2005; Vol. 1, p 212.
220. Minisci, F.; Recupero, F.; Cecchetto, A.; Punta, C.; Gambarotti, C.; Fontana, F.; Pedulli, G. F. J. Heterocycl. Chem. 2003, 40, 325.
221. Minisci, F.; Recupero, F.; Punta, C.; Gainbarotti, C.; Antonietti, F.; Fontana, F.; Pedulli, G. F. Chem. Commun. 2002, 2496.