Mild and selective Ru-catalyzed formylation and Fe-catalyzed acylation of free (N-H) indoles using anilines as the carbonyl source

Journal of the American Chemical Society

Volumn 133, Issue 31, 2011, Pages 11924-11927

  Wu, Wenliang ^a   Su, Weiping ^a  

^a FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FORMYLATION; GOOD YIELD; METHYL GROUP; N-METHYL ANILINE; OXIDATIVE COUPLINGS;

ACYLATION; ANILINE; FUNCTIONAL GROUPS;

CATALYSIS;

ANILINE DERIVATIVE; CARBON 13; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; IRON; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE;

ALDEHYDES; ANILINE COMPOUNDS; CATALYSIS; FERROUS COMPOUNDS; INDOLES; KETONES; MOLECULAR STRUCTURE; RUTHENIUM COMPOUNDS; STEREOISOMERISM;

EID: 79961133553     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2048495     Document Type: Article

References (79)

1. For examples of the recently developed transition metal-catalyzed synthesis and transformation of indoles, see: Gabriele, B.; Mancuso, R.; Salerno, G.; Lupinacci, E.; Ruffolo, G.; Costa, M. J. Org. Chem. 2008, 73, 4971
2. Gabriele, B.; Veltri, L.; Salerno, G.; Mancuso, R.; Costa, M. Adv. Synth. Catal. 2010, 352, 3355
3. Shen, L.; Zhang, M.; Wu, Y.; Qin, Y. Angew. Chem., Int. Ed. 2008, 47, 3618
4. Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447
5. Gribble, G. W. Pure. Appl. Chem. 2003, 75, 1417
6. Roy, S.; Roy, S.; Gribble, G. W. Org. Lett. 2006, 8, 4975
7. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
8. Nakamura, M.; Iiies, L.; Otsubo, S.; Nakamura, E. Org. Lett. 2006, 8, 2803
9. Potavathri, S.; Pereira, K. C.; Gorelsky, S. I.; Pike, A.; Lebris, A. P.; DeBoef, B. J. Am. Chem. Soc. 2010, 132, 14676
10. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 7870
11. Robbins, D. W.; Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 4068
12. Guo, C.; Song, J.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2010, 49, 5558
13. Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
14. Cai, Q.; Zhao, Z.-A.; You, S.-L. Angew. Chem., Int. Ed. 2009, 48, 7428
15. Wu, Q.-F.; He, H.; Liu, W.-B.; You, S.-L. J. Am. Chem. Soc. 2010, 132, 11418
16. Klare, H. T.; Oestreich, M.; Ito, J.-i.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312
17. Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7481
18. Perron, J.; Joseph, B.; Mérour, J.-Y. Tetrahedron Lett. 2003, 44, 6553
19. Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972
20. Wang, Z.; Li, K.; Zhao, D.; Lan, J.; You, J. Angew. Chem., Int. Ed. 2011, 50, 5365
21. Newhouse, T.; Lewis, C. A.; Eastman, K. J.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 7119
22. Coldham, I.; Dobson, B. C.; Fletcher, S. R.; Franklin, A. I. Eur. J. Org. Chem. 2007, 16, 2676
23. Lauchli, R.; Shea, K. J. Org. Lett. 2006, 8, 5287
24. Tohyama, S.; Choshi, T.; Matsumoto, K.; Yamabuki, A.; Ikegata, K.; Nobuhiro, J.; Hibino, S. Tetrahedron Lett. 2005, 46, 5263
25. Macor, J. E.; Blank, D. H.; Fox, C. B.; Lebel, L. A.; Newman, M. E.; Post, R. J.; Ryan, K.; Schmidt, A. W.; Schulz, D. W.; Koe, B. K. J. Med. Chem. 1994, 37, 2509
26. Birgit, P.; Thorsten, B. Synthesis 2007, 7, 1103
27. James, P. N.; Snyder, H. R. Org. Synth. 1959, 39, 30
28. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
29. Powers, J. C. J. Org. Chem. 1965, 30, 2534
30. Blume, R. C.; Lindwall, H. G. J. Org. Chem. 1945, 10, 255
31. Bennasar, M.-L.; Zulaica, E.; Sole, D.; Alonso, S. Tetrahedron. 2007, 63, 861
32. Mayer, S.; Joseph, B.; Guillaumet, G.; Merour, J.-Y. Synthesis 2002, 13, 1871
33. Niel, M. B.; Collins, I.; Beer, M. S. J. Med. Chem. 1999, 42, 2087
34. Wenkert, E.; Moeller, P. D. R.; Piettre, S. R.; McPhail, A. T. J. Org. Chem. 1988, 53, 3170
35. Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451
36. Okauchi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. Org. Lett. 2000, 2, 1485
37. Ottoni, O.; Neder, A.; de, V. F.; Dias, A. K. B.; Cruz, R. P. A.; Aquino, L. B. Org. Lett. 2001, 3, 1005
38. Katritzky, A. R.; Suzuki, K.; Singh, S. K.; He, H.-Y. J. Org. Chem. 2003, 68, 5720
39. Davidsen, S. K.; Summers, J. B.; Albert, D. H.; Holms, J. H.; Heyman, H. R.; Magoc, T. J.; Conway, R. G.; Rhein, D. A.; Carter, G. W. J. Med. Chem. 1994, 37, 4423
40. Szmuszkovicz, J. J. Am. Chem. Soc. 1960, 82, 1180
41. Bergman, J.; Venemalm, L. Tetrahedeon. 1990, 46, 6061
42. Murahashi, S.-I.; Zhang, D. Chem. Soc. Rev. 2008, 37, 1490
43. Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005
44. Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312
45. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
46. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968
47. Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176
48. Catino, A. J.; Nichols, J. M.; Nettles, B. J.; Doyle, M. P. J. Am. Chem. Soc. 2006, 128, 5648
49. Wang, M.-Z.; Zhou, C.-Y.; Wong, M.-K.; Che, C.-M. Chem.- Eur. J. 2010, 16, 5723
50. Volla, C. R.; Vogel, P. Org. Lett. 2009, 11, 1701
51. Li, S.; Wu, J. Org. Lett. 2011, 13, 712
52. Huang, L.; Zhang, X.; Zhang, Y. Org. Lett. 2009, 11, 3730
53. Yang, F.; Li, J.; Xie, J.; Huang, Z.-Z. Org. Lett. 2010, 12, 5214
54. Chu, L.; Zhang, X.; Qing, F.-L. Org. Lett. 2009, 11, 2197
55. Cheng, D.; Bao, W. J. Org. Chem. 2008, 73, 6881
56. Cheng, D.; Bao, W. Adv. Synth. Catal. 2008, 350, 1263
57. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
58. Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833
59. Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28
60. Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174
61. Yin, G.; Wu, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 11978
62. Bao, H.; Qi, X.; Tambar, U. K. J. Am. Chem. Soc. 2011, 133, 1206
63. Yoo, E. J.; Ma, S.; Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652
64. Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1
65. Wu, W.; Xu, J.; Huang, S.; Su, W. Chem. Commun. 2011, DOI: 10.1039/C1CC10545K.
66. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578
67. Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229
68. Yang, J.; Wang, Z.; Pan, F.; Li, Y.; Bao, W. Org. Biomol. Chem. 2010, 8, 2975
69. Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242
70. For some recently developed Fe-catalyzed cross-coupling reactions, see: Chen, M. S.; White, M. C. Science 2010, 327, 566
71. Chen, M. S.; White, M. C. Science 2007, 318, 783
72. Li, B.-J.; Xu, L.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656
73. Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Liu, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817
74. Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem., Int. Ed. 2008, 47, 8897
75. Bedford, R. B.; Betham, M.; Bruce, D. W.; Danopoulos, A. A.; Frost, R. M.; Hird, M. J. Org. Chem. 2006, 71, 1104
76. Bedford, R. B.; Hall, M. A.; Hodges, G. R.; Huwe, M.; Wilkinson, M. C. Chem. Commun. 2009, 6430
77. Murahashi, S.-I.; Naota, T.; Taki, H. J. Chem. Soc., Chem. Commun. 1985, 613
78. Horner, L.; Junkermann, H. Justus Liebigs Ann. Chem. 1955, 591, 53
79. Horner, L.; Kirmse, W. Justus Liebigs Ann. Chem. 1955, 597, 48