Hypervalent Iodine(III) in Direct Oxidative Amination of Arenes with Heteroaromatic Amines

Organic Letters

Volumn 17, Issue 18, 2015, Pages 4588-4591

  Manna, Srimanta ^a,b   Serebrennikova, Polina O ^a,c   Utepova, Irina A ^c   Antonchick, Andrey P ^a,b   Chupakhin, Oleg N ^c  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

^c URAL FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84941914252     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02320     Document Type: Article

References (84)

1. Song, G. Y.; Wang, F.; Li, X. W. Chem. Soc. Rev. 2012, 41, 3651 10.1039/c2cs15281a
2. Ramirez, T. A.; Zhao, B. G.; Shi, Y. Chem. Soc. Rev. 2012, 41, 931 10.1039/C1CS15104E
3. Du Bois, J. Org. Process Res. Dev. 2011, 15, 758 10.1021/op200046v
4. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926 10.1039/c0cs00095g
5. Aubin, Y.; Fischmeister, C.; Thomas, C. M.; Renaud, J. L. Chem. Soc. Rev. 2010, 39, 4130 10.1039/c003692g
6. Liang, C. G.; Collet, F.; Robert-Peillard, F.; Muller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343 10.1021/ja076519d
7. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534 10.1021/ar800098p
8. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318 10.1021/cr068006f
9. Blaser, H. U.; Indolese, A.; Naud, F.; Nettekoven, U.; Schnyder, A. Adv. Synth. Catal. 2004, 346, 1583 10.1002/adsc.200404156
10. Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675 10.1021/cr960433d
11. Starkov, P.; Jamison, T. F.; Marek, I. Chem.-Eur. J. 2015, 21, 5278 10.1002/chem.201405779
12. Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040 10.1021/acs.accounts.5b00020
13. Gephart, R. T.; Warren, T. H. Organometallics 2012, 31, 7728 10.1021/om300840z
14. Beletskaya, I. P.; Cheprakov, A. V. Organometallics 2012, 31, 7753 10.1021/om300683c
15. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068 10.1039/c1cs15082k
16. Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061 10.1039/b905820f
17. Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284 10.1038/nchembio0606-284
18. Macarulla, T.; Cervantes, A.; Tabernero, J.; Rosello, S.; Van Cutsem, E.; Tejpar, S.; Prenen, H.; Martinelli, E.; Troiani, T.; Laffranchi, B.; Jego, V.; von Richter, O.; Ciardiello, F. Br. J. Cancer 2015, 112, 1874 10.1038/bjc.2015.144
19. Martinelli, E.; Troiani, T.; D'Aiuto, E.; Morgillo, F.; Vitagliano, D.; Capasso, A.; Costantino, S.; Ciuffreda, L. P.; Merolla, F.; Vecchione, L.; De Vriendt, V.; Tejpar, S.; Nappi, A.; Sforza, V.; Martini, G.; Berrino, L.; De Palma, R.; Ciardiello, F. Int. J. Cancer 2013, 133, 2089 10.1002/ijc.28236
20. Koley, M.; Mike, A. K.; Heher, P.; Koenig, X.; Schoen, M.; Schnuerch, M.; Hilber, K.; Weitzer, G.; Mihovilovic, M. D. MedChemComm 2013, 4, 1189 10.1039/c3md00101f
21. Mitchell, W. L.; Giblin, G. M. P.; Naylor, A.; Eatherton, A. J.; Slingsby, B. P.; Rawlings, A. D.; Jandu, K. S.; Haslam, C. P.; Brown, A. J.; Goldsmith, P.; Clayton, N. M.; Wilson, A. W.; Chessell, I. P.; Green, R. H.; Whittington, A. R.; Wall, I. D. Bioorg. Med. Chem. Lett. 2009, 19, 259 10.1016/j.bmcl.2008.10.118
22. Niculescu-Duvaz, I.; Roman, E.; Whittaker, S. R.; Friedlos, F.; Kirk, R.; Scanlon, I. J.; Davies, L. C.; Niculescu-Duvaz, D.; Marais, R.; Springer, C. J. J. Med. Chem. 2008, 51, 3261 10.1021/jm070776b
23. Chen, Y. L.; Obach, R. S.; Braselton, J.; Corman, M. L.; Forman, J.; Freeman, J.; Gallaschun, R. J.; Mansbach, R.; Schmidt, A. W.; Sprouse, J. S.; Tingley, F. D., III; Winston, E.; Schulz, D. W. J. Med. Chem. 2008, 51, 1385 10.1021/jm070579c
24. Lascelles, B. D. X.; Court, M. H.; Hardie, E. M.; Robertson, S. A. Vet. Anaesth. Analg. 2007, 34, 228 10.1111/j.1467-2995.2006.00322.x
25. Zhou, Y.; Levitt, R. C.; Nicolaides, N. C.; Jones, S.; McLane, M.; U.S. patent 07504409, March 17, 2009.
26. Sambiagio, C.; Marsden, S. P.; Blacker, A. J.; McGowan, P. C. Chem. Soc. Rev. 2014, 43, 3525 10.1039/c3cs60289c
27. Lin, H.; Sun, D. Q. Org. Prep. Proced. Int. 2013, 45, 341 10.1080/00304948.2013.816208
28. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954 10.1002/anie.200804497
29. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337 10.1016/j.ccr.2004.09.014
30. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338 10.1002/anie.200800497
31. Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348, 23 10.1002/adsc.200505158
32. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L
33. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852 10.1021/ar970282g
34. Bariwal, J.; Van der Eycken, E. Chem. Soc. Rev. 2013, 42, 9283 10.1039/c3cs60228a
35. Louillat, M. L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901 10.1039/C3CS60318K
36. Shang, M.; Sun, S. Z.; Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2014, 136, 3354 10.1021/ja412880r
37. Yan, Q. Q.; Chen, Z. K.; Yu, W. L.; Yin, H.; Liu, Z. X.; Zhang, Y. H. Org. Lett. 2015, 17, 2482 10.1021/acs.orglett.5b00990
38. Marchetti, L.; Kantak, A.; Davis, R.; DeBoef, B. Org. Lett. 2015, 17, 358 10.1021/ol5034805
39. Jones, A. W.; Louillat-Habermeyer, M. L.; Patureau, F. W. Adv. Synth. Catal. 2015, 357, 945 10.1002/adsc.201401136
40. Xu, H.; Qiao, X. X.; Yang, S. P.; Shen, Z. M. J. Org. Chem. 2014, 79, 4414 10.1021/jo5003592
41. Louillat, M. L.; Biafora, A.; Legros, F.; Patureau, F. W. Angew. Chem., Int. Ed. 2014, 53, 3505 10.1002/anie.201308601
42. Kim, H.; Shin, K.; Chang, S. J. Am. Chem. Soc. 2014, 136, 5904 10.1021/ja502270y
43. Biafora, A.; Patureau, F. W. Synlett 2014, 25, 2525 10.1055/s-0034-1378999
44. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043 10.1002/anie.201300135
45. Shrestha, R.; Mukherjee, P.; Tan, Y. C.; Litman, Z. C.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 8480 10.1021/ja4032677
46. Louillat, M. L.; Patureau, F. W. Org. Lett. 2013, 15, 164 10.1021/ol303216u
47. Xiao, B.; Gong, T. J.; Xu, J.; Liu, Z. J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466 10.1021/ja108450m
48. John, A.; Nicholas, K. M. J. Org. Chem. 2011, 76, 4158 10.1021/jo200409h
49. Zhao, H. Q.; Wang, M.; Su, W. P.; Hong, M. C. Adv. Synth. Catal. 2010, 352, 1301 10.1002/adsc.200900856
50. Thu, H. Y.; Yu, W. Y.; Che, C. M. J. Am. Chem. Soc. 2006, 128, 9048 10.1021/ja062856v
51. Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 6790 10.1021/ja061715q
52. Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. J. Am. Chem. Soc. 2011, 133, 16382 10.1021/ja207296y
53. Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960 10.1021/ja2087085
54. Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605 10.1002/anie.201102984
55. Samanta, R.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P. Org. Lett. 2012, 14, 5518 10.1021/ol302607y
56. Louillat-Habermeyer, M. L.; Jin, R. W.; Patureau, F. W. Angew. Chem., Int. Ed. 2015, 54, 4102 10.1002/anie.201500089
57. Charushin, V. N.; Chupakhin, O. N. In Metal-Free C-H Functionalization of Aromatic Compounds through the Action of Nucleophilic Reagents; Topics in Heterocyclic Chemistry; Springer International Publishing: Cham, 2014; Vol. 37, pp 1-50.
58. Samanta, R.; Matcha, K.; Antonchick, A. P. Eur. J. Org. Chem. 2013, 2013, 5769 10.1002/ejoc.201300286
59. Samanta, R.; Antonchick, A. P. Synlett 2012, 23, 809 10.1055/s-0031-1290531
60. Samanta, R.; Narayan, R.; Bauer, J. O.; Strohmann, C.; Sievers, S.; Antonchick, A. P. Chem. Commun. 2015, 51, 925 10.1039/C4CC08376H
61. Manna, S.; Narayan, R.; Golz, C.; Strohmann, C.; Antonchick, A. P. Chem. Commun. 2015, 51, 6119 10.1039/C5CC00533G
62. Bering, L.; Antonchick, A. P. Org. Lett. 2015, 17, 3134 10.1021/acs.orglett.5b01456
63. Narayan, R.; Antonchick, A. P. Chem.-Eur. J. 2014, 20, 4568 10.1002/chem.201400186
64. Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 11960 10.1002/anie.201406464
65. Manna, S.; Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 8163 10.1002/anie.201403712
66. Manna, S.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 7324 10.1002/anie.201404222
67. Song, Z. Q.; Samanta, R.; Antonchick, A. P. Org. Lett. 2013, 15, 5662 10.1021/ol402626t
68. Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985 10.1002/anie.201303550
69. Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 2082 10.1002/anie.201208851
70. Antonchick, A. P.; Burgmann, L. Angew. Chem., Int. Ed. 2013, 52, 3267 10.1002/anie.201209584
71. Samanta, R.; Lategahn, J.; Antonchick, A. P. Chem. Commun. 2012, 48, 3194 10.1039/c2cc30324h
72. Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds; John Wiley & Sons, Ltd: Chichester, 2014.
73. Brown, M.; Delorme, M.; Malmedy, F.; Malmgren, J.; Olofsson, B.; Wirth, T. Synlett 2015, 26, 1573 10.1055/s-0034-1380687
74. Narayan, R.; Manna, S.; Antonchick, A. P. Synlett 2015, 26, 1785 10.1055/s-0034-1379912
75. Zhdankin, V. V.; Protasiewicz, J. D. Coord. Chem. Rev. 2014, 275, 54 10.1016/j.ccr.2014.04.007
76. Singh, F. V.; Wirth, T. Chem.-Asian J. 2014, 9, 950 10.1002/asia.201301582
77. Romero, R. M.; Woste, T. H.; Muniz, K. Chem.-Asian J. 2014, 9, 972 10.1002/asia.201301637
78. Roche, S. P.; Porco, J. A. Angew. Chem., Int. Ed. 2011, 50, 4068 10.1002/anie.201006017
79. Merritt, E. A.; Olofsson, B. Synthesis 2011, 2011, 517 10.1055/s-0030-1258328
80. Brand, J. P.; Gonzalez, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102 10.1039/C0CC02265A
81. Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086 10.1039/b823399c
82. Dohi, T.; Kita, Y. Chem. Commun. 2009, 2073 10.1039/b821747e
83. Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Tetrahedron 2009, 65, 10797 10.1016/j.tet.2009.10.040
84. Monir, K.; Ghosh, M.; Mishra, S.; Majee, A.; Hajra, A. Eur. J. Org. Chem. 2014, 2014, 1096 10.1002/ejoc.201301209