Nucleophilic substitutions and radical reactions of phenylazocarboxylates

Journal of Organic Chemistry

Volumn 77, Issue 3, 2012, Pages 1520-1532

  Jasch, Hannelore ^a   Höfling, Sarah B ^a   Heinrich, Markus R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; ALIPHATIC AMINES; AROMATIC AMINES; AROMATIC CORES; ARYL-ARYL COUPLING; BENZENE RING; BUILDING BLOCKES; ELEVATED TEMPERATURE; NUCLEOPHILIC SUBSTITUTIONS; RADICAL REACTIONS; SYNTHETIC ORGANIC CHEMISTRY;

AMINES; BENZENE; OXYGENATION;

REACTION KINETICS;

ALCOHOL; ALIPHATIC AMINE; AMIDE; AROMATIC AMINE; ARYL ACYLAMIDASE; AZOCARBOXAMIDE; BENZENE; BUTYLOXYCARBONYLAZO; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PHENYLAZOCARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHALOGENATION; CARBOHYDROXYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HALOGENATION; NUCLEOPHILICITY; ORGANIC CHEMISTRY; OXYGENATION; RADICAL REACTION; SUBSTITUTION REACTION; SYNTHESIS;

AZO COMPOUNDS; CARBOXYLIC ACIDS; CHEMISTRY TECHNIQUES, SYNTHETIC; FREE RADICALS; TEMPERATURE;

EID: 84856682200     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202406k     Document Type: Article

References (106)

1. Bunnett, J. F.; Zahler, J. E. Chem. Rev. 1951, 49, 273
2. Crampton, M. R. Org. React. Mech. 2008, 155
3. Terrier, F. Nucleophilic Aromatic Displacement; VCH: New York, 1991.
4. Zoltewicz, A. J. Top. Curr. Chem. 1975, 59, 33
5. For rate determining factors, see: Fernandez, I.; Frenking, G.; Uggerud, E. J. Org. Chem. 2010, 75, 2971
6. Cruz, H.; Gallardo, I.; Guirado, G. Green Chem. 2011, 13, 2531
7. Chai, Y.; Jiang, K.; Sun, C.; Pan, Y. Chem.-Eur. J. 2011, 17, 10820
8. Rebeck, N. T.; Knauss, D. M. Macromolecules 2011, 44, 6717
9. Zeika, O.; Li, Y.; Jockusch, S.; Parkin, G.; Sattler, A.; Sattler, W.; Turro, N. J. Org. Lett. 2010, 12, 3696
10. Jacobsson, M.; Oxgaard, J.; Abrahamsson, C.-O.; Norrby, P.-O.; Goddard, W. A., III; Ellervik, U. Chem.-Eur. J. 2008, 14, 3954
11. DeRoy, P. L.; Surprenant, S.; Bertrand-Laperle, M.; Yoakim, C. Org. Lett. 2007, 9, 2741
12. Kondoh, A.; Yorimitsu, H.; Oshima, K. Tetrahedron 2006, 62, 2357
13. Yeom, C.-E.; Kim, H. W.; Lee, S. Y.; Kim, B. M. Synlett 2007, 146
14. The nitro group can be employed to generate alkyl but not aryl radicals: Ono, N.; Kaji, A. Synthesis 1986, 693
15. Galli, C. Chem. Rev. 1988, 88, 765
16. Studer, A.; Bossart, M. In Radicals in Organic Synthesis, 2 nd ed.; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
17. Bowman, W. R.; Storey, J. M. D. Chem. Soc. Rev. 2007, 36, 1803
18. Vaillard, S. E.; Schulte, B.; Studer, A. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, Germany, 2009.
19. Pratsch, G.; Heinrich, M. R. Top. Curr. Chem. 2011, not supplied.
20. Dickschat, A.; Studer, A. Org. Lett. 2010, 12, 3972
21. Demir, A. S.; Reis, Ö.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578
22. Demir, A. S.; Reis, Ö.; Özgül-Karaaslan, E. J. Chem. Soc., Perkin. Trans. 1 2001, 3042
23. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. Chem.-Eur. J. 2011, 17, 4307
24. Zollinger, H. Acc. Chem. Res. 1973, 6, 3357
25. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
26. Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96
27. Dey, B. B.; Govindachari, T. R.; Rajagopalan, S. C. Curr. Sci. 1946, 15, 161
28. Meldola, R.; Stephens, F. G. C. J. Chem. Soc. 1905, 87, 1199
29. Huisgen, R. Liebigs Ann. Chem. 1948, 559, 101
30. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1897, 30, 2334
31. Hantzsch, A.; Smythe, J. S. Ber. Dtsch. Chem. Ges. 1900, 33, 505
32. Wang, M.; Funabiki, K.; Matsui, M. Dyes Pigm. 2003, 57, 77
33. Hunger, K.; Mischke, P.; Rieper, W.; Raue, R.; Kunde, K.; Engel, A. Azo Dyes in Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
34. Goeminne, A.; Scammells, P. J.; Devine, S. M.; Flynn, B. L. Tetrahedron Lett. 2010, 51, 6882
35. Liu, C.-Y.; Gavryushin, A.; Knochel, P. Chem.-Asian J. 2007, 2, 1020
36. Pazo-Llorente, R.; Maskill, H.; Bravo-Díaz, C.; González-Romero, E. Eur. J. Org. Chem. 2006, 2201
37. Pazo-Llorente, R.; Bravo-Díaz, C.; González-Romero, E. Eur. J. Org. Chem. 2004, 3221
38. Pete, B. Tetrahedron Lett. 2008, 49, 2835
39. Li, J. Japp-Klingemann Hydrazone Synthesis in Name Reactions for Functional Group Transformations; Li, J. J.; Corey, E. J., Eds.; John Wiley & Sons: Hoboken, NJ, 2007; p 630-634.
40. Jiricek, J.; Blechert, S. J. Am. Chem. Soc. 2004, 126, 3534
41. Laali, K. K.; Gettwert, V. J. J. Fluorine Chem. 2001, 107, 31
42. Yoneda, N.; Fukuhara, T. Tetrahedron 1996, 52, 23
43. Faucher, N.; Ambroise, Y.; Cintrat, J.-C.; Doris, E.; Pillon, F.; Rousseau, B. J. Org. Chem. 2002, 67, 932
44. 3, see: Nguyen, N. H.; Cougnon, C.; Gohier, F. J. Org. Chem. 2009, 74, 3955
45. For nucleophiles acting as reductants, see: Fernández-Alonso, A.; Bravo-Díaz, C. Helv. Chim. Acta 2010, 93, 877
46. Höfling, S. B.; Bartuschat, A. L.; Heinrich, M. R. Angew. Chem., Int. Ed. 2010, 47, 9769
47. Milne, H. B.; Kilday, W. J. Org. Chem. 1965, 30, 64
48. Blaschke, H.; Brunn, E.; Huisgen, R.; Mack, W. Chem. Ber. 1972, 105, 2841
49. Bowman, W. R.; Forshaw, J. A.; Hall, K. P.; Kitchin, J. P.; Mott, A. W. Tetrahedron 1996, 52, 3961
50. Wilshire, J. F. K. Aust. J. Chem. 1988, 41, 995
51. Snape, T. J. Chem. Soc. Rev. 2008, 37, 2452
52. Borsche, W. Ber. Dtsch. Chem. Ges. 1923, 66, 1488
53. Ogata, Y.; Okano, M. J. Am. Chem. Soc. 1949, 71, 3211
54. Beckwith, A. L. J.; Miller, J. J. Org. Chem. 1954, 19, 1708
55. Crampton, M. R.; Emokpae, T. A.; Isanbor, C.; Batsanov, A. S.; Howard, J. A. K.; Mondal, R. Eur. J. Org. Chem. 2006, 1222
56. Crampton, M. R.; Emokpae, T. A.; Howard, J. A. K.; Isanbor, C.; Mondal, R. Org. Biomol. Chem. 2003, 1, 1004
57. Crampton, M. R.; Emokpae, T. A.; Isanbor, C. J. Phys. Org. Chem. 2006, 19, 75
58. Urankar, D.; Steinbücher, M.; Kosjek, J.; Košmrlj, J. Tetrahedron 2010, 66, 2602
59. Stahl, G. L.; Walter, R.; Smith, C. W. J. Org. Chem. 1978, 43, 2285
60. Cohen, S. G.; Nicholson, J. J. Am. Chem. Soc. 1964, 86, 3892
61. Cohen, S. G.; Nicholson, J. J. Org. Chem. 1965, 30, 1162
62. Hoffmann, R. W. Chem. Ber. 1965, 98, 222
63. For a report on arylazocarboxylates (and aryl diazenes) as photoaffinity probes for heme-containing proteins, see: Tschirret-Guth, R. A.; Ortiz de Montellano, P. R. J. Org. Chem. 1998, 63, 9711
64. Huang, P. C.; Kosower, E. M. J. Am. Chem. Soc. 1967, 89, 3910
65. Myers, A. G.; Movassaghi, M.; Zheng, B. Tetrahedron Lett. 1997, 38, 6569
66. Taniguchi, T.; Sugiura, Y.; Zaimoku, H.; Ishibashi, H. Angew. Chem., Int. Ed. 2010, 49, 10154
67. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. Chem.-Eur. J. 2011, 17, 4307
68. Recent examples for the synthesis of phenols from aryl diazonium salts have been reported by: Canning, P. S. J.; Maskill, H.; McCrudden, K.; Sexton, B. Bull. Chem. Soc. Jpn. 2002, 75, 789
69. For a review on Meerwein-type olefin functionalizations, see: Heinrich, M. R. Chem.-Eur. J. 2009, 15, 820
70. Heinrich, M. R.; Wetzel, A.; Kirschstein, M. Org. Lett. 2007, 9, 3833
71. Dickschat, A.; Studer, A. Org. Lett. 2010, 12, 3972
72. Garden, S. J.; Avila, D. V.; Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1996, 61, 805
73. Blank, O.; Wetzel, A.; Ullrich, D.; Heinrich, M. R. Eur. J. Org. Chem. 2008, 3179
74. For a comparable base-catalyzed fragmentation, see: Richardson, W. H.; Heesen, T. C. J. Org. Chem. 1972, 37, 3416
75. Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19
76. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465
77. Downham, R.; Ng, F. W.; Overman, L. E. J. Org. Chem. 1998, 63, 8096
78. Krakowiak, K. E.; Bradshaw, J. S. Synth. Commun. 1996, 26, 3999
79. For the thermal cyclization of a few 2,6-dimethylphenylazo compounds to indazole derivatives, see: Fusco, R.; Marchesini, A.; Sannicolo, F. J. Heterocycl. Chem. 1987, 24, 773
80. Aryl radicals are considered as electrophilic when compared to other carbon-centered radicals. On a general scale including strongly electrophilic radicals such as fluorine, they have been classified as moderate to weak nucleophiles: De Vleeschouwer, F.; van Speybroeck, V.; Waroquier, M.; Geerlings, P.; de Proft, F. Org. Lett. 2007, 9, 2721
81. For comparable observations in Pschorr-type cyclization reactions, see: Moorthy, J. N.; Samanta, S. J. Org. Chem. 2007, 72, 9786
82. For photochemical properties of comparable compounds (also in the presence of TEMPO), see: Heinrich, M. R.; Kirschstein, M. Tetrahedron Lett. 2006, 47, 2115 and references cited therein
83. Singer, K. D.; Sohn, J. E.; King, L. A.; Gordon, H. M.; Katz, H. E.; Dirk, C. W. J. Opt. Soc. Am. B 1989, 6, 1339
84. Tšubrik, O.; Kisseljova, K.; Mäeorg, U. Synlett 2006, 2391
85. Tšubrik, O.; Sillard, R.; Mäeorg, U. Synthesis 2006, 843
86. Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 897
87. Zhu, M.; Zheng, N. Synthesis 2011, 2223
88. Jurberg, I. D.; Gagosz, F. J. Organomet. Chem. 2011, 696, 37
89. Kisseljova, K.; Tšubrik, O.; Sillard, R.; Mäeorg, S.; Mäeorg, U. Org. Lett. 2006, 8, 43
90. Forchiassin, M.; Risaliti, A.; Russo, C. Tetrahedron 1981, 37, 2921
91. Ballaben, E.; Forchiassin, M.; Nitti, P.; Russo, C. Gazz. Chim. Ital. 1993, 123, 387
92. Korotkov, V. S.; Larionov, O. V.; Hofmeister, A.; Magull, J.; de Meijere, A. J. Org. Chem. 2007, 72, 7504
93. Huang, X.-L.; He, L.; Shao, P.-L.; Ye, S. Angew. Chem., Int. Ed. 2009, 48, 192
94. Alonso, F.; Radivoy, G.; Yus, M. Tetrahedron 2000, 56, 8673
95. Mortarini, V.; Calvino, R.; Gasco, A.; Ferrarotti, B.; Sanfilippo, A.; Schioppacassi, G. Eur. J. Med. Chem. 1980, 15, 475
96. Dekeyser, M. A.; McDonald, P. T. (Chemtura Corp), PCT2008144116, 2008.
97. Dekeyser, M. A.; McDonald, P. T. (Chemtura Corp), US7399757 (B1), 2008.
98. Ruoho, A. E.; Hajipour, A. R.; Chu, U. B.; Fontanilla, D. A. (Wisconsin Alumni Research Foundation), WO2010/59711 A1, 2010.
99. Vahirua-Lechat, I.; Menut, C.; Roig, B.; Bessiere, J. M.; Lamaty, G. Phytochemistry 1996, 43, 1277
100. El-Gendy, A. A.; Said, M. M.; Ghareb, N.; Mostafa, Y. M.; El-Ashry, E. S. H. Arch. Pharm. Chem. Life Sci. 2008, 341, 294
101. Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem.-Eur. J. 2002, 8, 3901
102. Xu, H.-J.; Liang, Y.-F.; Cai, Z.-Y.; Qi, H.-X.; Yang, C.-Y.; Feng, Y.-S. J. Org. Chem. 2011, 76, 2296
103. Armstrong, A.; Jones, L. H.; Knight, J. D.; Kelsey, R. D. Org. Lett. 2005, 7, 713
104. He, C.; Guo, S.; Huang, L.; Lei, A. J. Am. Chem. Soc. 2010, 132, 8273
105. Dai, J.-J.; Liu, J.-H.; Luo, D.-F.; Liu, L. Chem. Commun. 2011, 47, 677
106. Effenberger, F.; Koch, M.; Streicher, W. Chem. Ber. 1991, 124, 163