Domino Oxidative [Pd]-Catalysis: One-Pot Synthesis of Fluorenones Starting from Simple Benzylamines and Iodo Arenes

Organic Letters

Volumn 17, Issue 23, 2015, Pages 5894-5897

  Ravi Kumar, Devarapalli ^a   Satyanarayana, Gedu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84948798282     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b03077     Document Type: Article

References (63)

1. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077 10.1002/adsc.200303094
2. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731 10.1021/cr0104330
3. Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem.-Eur. J. 2002, 8, 2423 10.1002/1521-3765(20020603)8:11<2422::AID-CHEM2422>3.0.CO;2-B
4. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439 10.1016/j.tet.2005.11.027
5. Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175 10.1126/science.1141956
6. Castro, L. C. M.; Chatani, N. Chem.-Eur. J. 2014, 20, 4548 10.1002/chem.201304978
7. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250 10.1021/ol901049r
8. Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046 10.1002/anie.200500589
9. Warratz, S.; Kornhaaß, C.; Cajaraville, A.; Niepötter, B.; Stalke, D.; Ackermann, L. Angew. Chem., Int. Ed. 2015, 54, 5513 10.1002/anie.201500600
10. Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2014, 50, 2442 10.1039/c3cc49398a
11. Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380 10.1002/anie.201005874
12. Xu, X.; Deng, Y.; Yim, D. N.; Zavalij, P. Y.; Doyle, M. P. Chem. Sci. 2015, 6, 2196 10.1039/C4SC03991B
13. Wang, X.; Lu, Y.; Dai, H. X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203 10.1021/ja105366u
14. Apers, S.; Vlietinck, A.; Pieters, L. Phytochem. Rev. 2003, 2, 201 10.1023/B:PHYT.0000045497.90158.d2
15. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156 10.1021/ja050366h
16. Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330 10.1021/ja051402f
17. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300 10.1021/ja031543m
18. Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem. 2005, 117, 2150 10.1002/ange.200462884
19. Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748 10.1021/ja064500p
20. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2008, 47, 9462 10.1002/anie.200804153
21. Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2002, 67, 9428 10.1021/jo0262006
22. Shabashov, D.; Daugulis, O.; Cheme, S. J. Org. Chem. 2008, 73, 7818 10.1021/jo801300y
23. Li, H.; Zhu, R. Y.; Shi, W. J.; He, K. H.; Shi, Z. J. Org. Lett. 2012, 14, 4850-4853 10.1021/ol302181z
24. Gandeepan, P.; Hung, C. H.; Cheng, C. H. Chem. Commun. 2012, 48, 9379 10.1039/c2cc34344d
25. Yang, G. Y.; Zhang, Q. H.; Miao, H.; Tong, X. L.; Xu, J. Org. Lett. 2005, 7, 263 10.1021/ol047749p
26. Shi, Z.; Glorius, F. Chem. Sci. 2013, 4, 829 10.1039/C2SC21823B
27. Wan, J.; Huang, J.; Jhan, Y.; Hsieh, J. Org. Lett. 2013, 15, 2742 10.1021/ol401063w
28. Zhao, J.; Yue, D.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2007, 129, 5288-5295 10.1021/ja070657l
29. Yang, G.; Zhang, Q.; Miao, H.; Tong, X.; Xu, J. Org. Lett. 2005, 7, 263 10.1021/ol047749p
30. Zhang, X.; Larock, R. C. Org. Lett. 2005, 7, 3973 10.1021/ol0514597
31. Waldo, J. P.; Zhang, X.; Shi, F.; Larock, R. C. J. Org. Chem. 2008, 73, 6679 10.1021/jo8009215
32. Venkatesan, K.; Dhivya, S.; Rethavathi, J.; Narasimhan, S. J. Chem. Pharm. Res. 2012, 4, 4477
33. Kingston, D. G. I.; Bursey, J. T.; Bursey, M. M.; Ionization, B. C. Chem. Rev. 1974, 74, 215 10.1021/cr60288a004
34. Sartori, G.; Maggi, R. Chem. Rev. 2006, 106, 1077 10.1021/cr040695c
35. Pschorr, R. Ber. Dtsch. Chem. Ges. 1896, 29, 496 10.1002/cber.18960290198
36. Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779 10.1002/anie.198007791
37. Ahrendt, K. A.; Borths, C. J.; Macmillan, D. W. C.; January, R. V. J. Am. Chem. Soc. 2000, 122, 4243 10.1021/ja000092s
38. Campo, M. A.; Larock, R. C. J. Org. Chem. 2002, 67, 5616 10.1021/jo020140m
39. Zhang, X.; Larock, R. C. Org. Lett. 2005, 7, 3973 10.1021/ol0514597
40. Lazareva, A.; Daugulis, O. Org. Lett. 2006, 8, 5211 10.1021/ol061919b
41. Mahendar, L.; Krishna, J.; Reddy, A. G. K.; Ramulu, B. V.; Satyanarayana, G. Org. Lett. 2012, 14, 628 10.1021/ol2032625
42. Mahendar, L.; Satyanarayana, G. J. Org. Chem. 2014, 79, 2059 10.1021/jo402763m
43. Mahendar, L.; Satyanarayana, G. J. Org. Chem. 2015, 80, 7089 10.1021/acs.joc.5b00888
44. Mahendar, L.; Reddy, A. G. K.; Krishna, J.; Satyanarayana, G. J. Org. Chem. 2014, 79, 8566 10.1021/jo501137q
45. Krishna, J.; Niharika, P.; Satyanarayana, G. RSC Adv. 2015, 5, 26749 10.1039/C5RA00955C
46. Krishna, J.; Reddy, A. G. K.; Satyanarayana, G. Tetrahedron Lett. 2014, 55, 861 10.1016/j.tetlet.2013.12.030
47. Reddy, A. G. K.; Krishna, J.; Satyanarayana, G. Tetrahedron Lett. 2012, 53, 5635 10.1016/j.tetlet.2012.08.023
48. Reddy, A. G. K.; Satyanarayana, G. Tetrahedron 2012, 68, 8003 10.1016/j.tet.2012.06.106
49. Krishna, J.; Reddy, A. G. K.; Satyanarayana, G. Synlett 2013, 24, 967 10.1055/s-0033-1338438
50. Tietze, L. F. Chem. Rev. 1996, 96, 115 10.1021/cr950027e
51. Satyanarayana, G.; Maier, M. E. Org. Lett. 2008, 10, 2361 10.1021/ol800330d
52. Satyanarayana, G.; Maichle-Mössmer, C.; Maier, M. E. Chem. Commun. 2009, 1571 10.1039/b820636h
53. Satyanarayana, G.; Maier, M. E. Eur. J. Org. Chem. 2008, 2008, 5543 10.1002/ejoc.200800724
54. Yadav, A. K.; Yadav, L. D. S. RSC Adv. 2014, 4, 34764 10.1039/C4RA05929H
55. Ahrendt, K. A.; Borths, C. J.; Macmillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243 10.1021/ja000092s
56. Saura-llamas, I.; Palin, M. G.; Jones, P. G.; Ram, M. C. Organometallics 1997, 16, 826 10.1021/om9609574
57. Gandeepan, P.; Cheng, C. H. J. Am. Chem. Soc. 2010, 132, 8569 10.1021/ja1026248
58. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527 10.1021/cr030681r
59. Kwon, M. S.; Kim, S.; Park, S.; Bosco, W.; Chidrala, R. K.; Park, J. J. Org. Chem. 2009, 1, 2877 10.1021/jo8026609
60. Maimone, T. J.; Buchwald J. Am. Chem. Soc. 2010, 132, 9990 10.1021/ja1044874
61. Kefalidis, C. E.; Holstein, P. M.; Clot, E.; Baudoin, O. J. Org. Chem. 2014, 79, 11903 10.1021/jo501610x
62. Janody, S.; Jazzar, R.; Comte, A.; Holstein, P. M.; Vors, J.-P.; Ford, M. J.; Baudoin, O. Chem.-Eur. J. 2014, 20, 11084 10.1002/chem.201402907
63. Ratnikov, M. O.; Xu, X.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 9475 10.1021/ja402479r