Oxidative radical arylation of anilines with arylhydrazines and dioxygen from air

Journal of Organic Chemistry

Volumn 79, Issue 5, 2014, Pages 2314-2320

  Hofmann, Josefa ^a   Jasch, Hannelore ^a   Heinrich, Markus R ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO FUNCTIONALITY; ARYLATION REACTIONS; ARYLATIONS; ARYLHYDRAZINES; GRAM SCALE; HIGH ORTHO; OPTIMIZED CONDITIONS; PARA POSITION;

AROMATIC COMPOUNDS; REACTION KINETICS;

ANILINE;

2 AMINOBIPHENYL DERIVATIVE; AMINOBIPHENYL DERIVATIVE; ANILINE; ARYLHYDRAZINE DERIVATIVE; HYDRAZINE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

AIR; ARTICLE; ARYLATION; CHEMICAL STRUCTURE; OXIDATION; RADICAL REACTION;

AIR; AMINOBIPHENYL COMPOUNDS; ANILINE COMPOUNDS; CATALYSIS; HYDRAZINES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; STEREOISOMERISM;

EID: 84896774870     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500063r     Document Type: Article

References (99)

1. Costantino, L.; Barlocco, D. Curr. Med. Chem. 2006, 13, 65
2. Jiang, H.; Sun, J.; Zhang, J. Curr. Org. Chem. 2012, 16, 2014
3. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447
4. Matsubara, S.; Asano, K.; Kajita, Y.; Yamamoto, M. Synthesis 2007, 2055
5. Price, J. R.; Lan, Y.; Brooker, S. J. Chem. Soc., Dalton Trans. 2007, 1807
6. Fliedel, C.; Maisse-Francois, A.; Bellemin-Laponnaz, S. Inorg. Chim. Acta 2007, 360, 143
7. Fedushkin, I. L.; Chudakova, V. A.; Skatova, A. A.; Khvoinova, N. M.; Kurskii, Y. A.; Glukhova, T. A.; Fukin, G. K.; Dechert, S.; Hummert, M.; Schumann, H. Z. Anorg. Allg. Chem. 2004, 630, 501
8. Pan, X.; Wilcox, C. S. J. Org. Chem. 2010, 75, 6445
9. Hoffmann-Emery, F.; Jakob-Roetne, R.; Flohr, A.; Bliss, F.; Reents, R. Tetrahedron Lett. 2009, 50, 6380
10. Eicken, K.; Rack, M.; Wetterich, F.; Ammermann, E.; Lorenz, G.; Strathmann, S. (BASF SE) DE19735224, 1999
11. Chem. Abstr. 1999, 130, 182464.
12. Eicken, K.; Rang, H.; Harreus, A.; Goetz, N.; Ammermann, E.; Lorenz, G.; Strathmann, S. (BASF SE) DE19531813, 1997
13. Chem. Abstr. 1997, 126, 264007.
14. Jörges, W.; Heinrich, J.-D.; Lantzsch, R. (Bayer Cropscience) WO2006024388, 2006
15. Chem. Abstr. 2006, 144, 253890.
16. Dietz, J.; Strathmann, S.; Stierl, R.; Montag, J. (BASF SE) WO 2007128756, 2007
17. Chem. Abstr. 2007, 147, 516420.
18. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, 2 nd ed.; Wiley-VCH: Weinheim, 2004.
19. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH: Weinheim, 2004.
20. Bonin, H.; Fouquet, E.; Felpin, F.-X. Adv. Synth. Catal. 2011, 353, 3063
21. Rouhi, A. M. Chem. Eng. News 2004, 82, 49
22. Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
23. Glasnov, T. N.; Kappe, C. O. Adv. Synth. Catal. 2010, 352, 3089
24. Caron, L.; Campeau, L.-C.; Fagnou, K. Org. Lett. 2008, 10, 4533
25. Felpin, F.-X.; Fouquet, E.; Zakri, C. Adv. Synth. Catal. 2009, 351, 649
26. Spivey, A. C.; Tseng, C.-C.; Hannah, J. P.; Gripton, C. J. G.; de Fraine, P.; Parr, N. J.; Scicinski, J. J. Chem. Commun. 2007, 2926
27. Bolton, R.; Williams, G. H. Chem. Soc. Rev. 1986, 15, 261
28. Studer, A. In Radicals in Organic Synthesis, 1 st ed.; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; p 44.
29. Bowman, W. R.; Storey, J. M. D. Chem. Soc. Rev. 2007, 36, 1803
30. Vaillard, S. E.; Schulte, B.; Studer, A. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009; p 475.
31. Dyker, G. Handbook of C-H Transformations; Wiley-VCH: Weinheim, 2005.
32. Ackermann, L. Top. Organomet. Chem. 2008, 24, 35
33. Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949
34. Lersch, M.; Tilset, M. Chem. Rev. 2005, 105, 2471
35. Ishikawa, A.; Nakao, Y.; Sato, H.; Sakaki, S. Dalton Trans. 2010, 39, 3279
36. Foley, N. A.; Ke, Z.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. Organometallics 2008, 27, 3007
37. Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F.-M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 458
38. Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305
39. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
40. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172
41. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593
42. Vallée, F.; Mousseau, J. J.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 1514
43. Liu, W.; Cao, H.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 2004
44. Pirali, T.; Zhang, F.; Miller, A. H.; Head, J. L.; McAusland, D.; Greaney, M. F. Angew. Chem., Int. Ed. 2012, 51, 1006
45. Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 46, 2339
46. Dermer, O. C.; Edmison, M. T. Chem. Rev. 1957, 57, 77
47. Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594
48. For the rate of addition of aryl radicals to benzene, see: Scaiano, J. C.; Stewart, L. C J. Am. Chem. Soc. 1983, 105, 3609
49. Galli, C. Chem. Rev. 1988, 88, 765
50. Kosynkin, D.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 4846
51. Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134, 2958
52. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566
53. Pratsch, G.; Wallaschkowski, T.; Heinrich, M. R. Chem.-Eur. J. 2012, 18, 11555
54. Vaillard, S. E.; Studer, A. Radical Arylations. In Encyclopedia of Radicals in Chemistry, Biology, and Materials; Chatgilialoglu, C.; Studer, A., Ed.; Wiley: New York, 2012; Vol. 2.
55. Jasch, H.; Heinrich, M. R. Tin Hydrides and Functional Group Transformations. In Encyclopedia of Radicals in Chemistry, Biology, and Materials; eds. Chatgilialoglu, C.; Studer, A., Eds.; Wiley: New York, 2012; Vol. 2.
56. Pratsch, G.; Heinrich, M. R. In Topics in Current Chemistry; Heinrich, M. R.; Gansäuer, A., Eds.; Springer: New York, 2012; Vol. 320.
57. Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673
58. Sun, C.-L.; Li, H.; Yu, D.-G.; Yu, M.; Zhou, X.; Lu, X.-Y.; Huang, K.; Zheng, S.-F.; Li, B.-J.; Shi, Z.-J. Nat. Chem. 2010, 2, 1044
59. Shirakawa, E.; Itoh, K.-I.; Higashino, T.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 15537
60. Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kwong, F. Y.; Lei, A. J. Am. Chem. Soc. 2010, 132, 16737
61. For possible reaction mechanisms, see: Studer, A.; Curran, D. Angew. Chem., Int. Ed. 2011, 50, 5018
62. Chaturbhuj, G. U.; Akamanchi, K. G. Tetrahedron Lett. 2011, 52, 4950
63. Curran, D. P.; Keller, A. I. J. Am. Chem. Soc. 2006, 128, 13706
64. Demir, A. S.; Reis, Ö.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578
65. Wetzel, A.; Ehrhardt, V.; Heinrich, M. R. Angew. Chem., Int. Ed. 2008, 47, 9130
66. Wetzel, A.; Pratsch, G.; Kolb, R.; Heinrich, M. R. Chem.-Eur. J. 2010, 16, 2547
67. Jasch, H.; Scheumann, J.; Heinrich, M. R. J. Org. Chem. 2012, 77, 10699
68. Taniguchi, T.; Sugiura, Y.; Zaimoku, H.; Ishibashi, H. Angew. Chem., Int. Ed. 2010, 49, 10154
69. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. Chem.-Eur. J. 2011, 17, 4307
70. Demir, A. S.; Reis, Ö.; Özgül-Karaaslan, E. J. Chem. Soc., Perkin Trans. 1 2001, 3042
71. Demir, A. S.; Findik, H. Tetrahedron 2008, 64, 6196
72. Demir, A. S.; Reis, Ö.; Emrullahoglu, M. Tetrahedron 2002, 58, 8055
73. Mohammadpoor-Baltork, I.; Hajipour, A. R.; Mohammadi, H. Bull. Chem. Soc. Jpn. 1998, 71, 1649
74. Johnson, M. D.; Hornstein, B. J. J. Chem. Soc., Chem. Commun. 1996, 965
75. Firouzabadi, H.; Mohajer, D.; Entezari-Moghadam, M. Bull. Chem. Soc. Jpn. 1988, 61, 2185
76. Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174
77. Hu, Z.; Kerton, F. M. Org. Biomol. Chem. 2012, 10, 1618
78. Hadjiarapoglou, L.; Spyroudis, S.; Varvoglis, A. Synthesis 1983, 207
79. Shine, H. J.; Zmuda, H.; Kwart, H.; Horgan, A. G.; Breichbiel, M. J. Am. Chem. Soc. 1982, 104, 5181
80. Shine, H. J.; Zmuda, H.; Park, K. H.; Kwart, H.; Horgan, A. G.; Brechbiel, M. J. Am. Chem. Soc. 1982, 104, 2501
81. Hoogewerff, S.; van Dorp, W. A. Chem. Ber. 1877, 10, 1936
82. Bamberger, E.; Tschirner, F. Chem. Ber. 1898, 31, 1522
83. Ruether, T.; Jackson, W. R.; Bond, A. M. Aust. J. Chem. 2002, 55, 691
84. Patel, S.; Mishra, B. K. Tetrahedron Lett. 2004, 45, 1371
85. Zhang, L.; Xia, J.; Li, Q.; Li, X.; Wang, S. Organometallics 2011, 30, 375
86. Chen, Z.-X.; Wang, G.-W. J. Org. Chem. 2005, 70, 2380
87. Coleman, G. H. Org. Synth. 1922, 2
88. Huang, P. C.; Kosower, E. M. J. Am. Chem. Soc. 1967, 89, 3910
89. Huang, P. C.; Kosower, E. M. J. Am. Chem. Soc. 1968, 90, 2367
90. Kosower, E. M.; Huang, P. C.; Tsuji, T. J. Am. Chem. Soc. 1969, 91, 2325
91. Myers, A. G.; Movassaghi, M.; Zheng, B. Tetrahedron Lett. 1997, 38, 6569
92. Braslau, R.; Burrill, L. C., II; Mahal, L. K.; Wedeking, T. Angew. Chem., Int. Ed. 1997, 36, 237
93. Amorati, R.; Valgimigli, L. Org. Biomol. Chem. 2012, 10, 4147
94. Hanthorn, J. J.; Valgimigli, L.; Pratt, D. A. J. Am. Chem. Soc. 2012, 134, 8306
95. Hanthorn, J. J.; Valgimigli, L.; Pratt, D. A. J. Org. Chem. 2012, 77, 6908
96. Moorthy, J. N.; Samanta, S. J. Org. Chem. 2007, 72, 9786
97. Amorati, R.; Ferroni, F.; Pedulli, G. F.; Valgimigli, L. J. Org. Chem. 2003, 68, 9654
98. Amorati, R.; Valgimigli, L.; Panzella, L.; Napolitano, A.; d'Ischia, M. J. Org. Chem. 2013, 78, 9857
99. Curran, D. P.; Keller, A. I. J. Am. Chem. Soc. 2006, 128, 13706