Deammoniative condensation of primary allylic amines with nonallylic amines

Chinese Journal of Chemistry

Volumn 32, Issue 8, 2014, Pages 741-751

  Wang, Yong ^a   Li, Manbo ^a   Ma, Xiantao ^a,b   Liu, Congrong ^a   Gu, Yonghong ^a   Tian, Shi Kai ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b NANJING INSTITUTE OF TECHNOLOGY   (China)

Author keywords

amines; deammoniation; palladium; stereospecificity; substitution

Indexed keywords

EID: 84906724106     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201400406     Document Type: Article

References (71)

1. Carey, F. A.,;, Sundberg, R. J., Advanced Organic Chemistry Part B: Reactions and Synthesis, 5 th ed., Springer, New York, 2007.
2. Tsuji, J.,. Acc. Chem. Res., 1969, 2, 144.
3. Trost, B. M.,. Tetrahedron, 1977, 33, 2615.
4. Trost, B. M.,;, Van Vranken, D. L.,. Chem. Rev., 1996, 96, 395.
5. Trost, B. M.,;, Crawley, M. L.,. Chem. Rev., 2003, 103, 2921.
6. Kazmaier, U.,;, Pohlman, M., In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., Eds.:, de Meijere, A.,;, Diederich, F., Wiley-VCH, Weinheim, 2004, p. 531.
7. Wuts, P. G. M.,;, Greene, T. W., Greene's Protective Groups in Organic Synthesis, 4 th ed., John Wiley & Sons, Inc., Hoboken, NJ, 2007.
8. For the formation of C-C bonds, see:, Murahashi, S.-I.,;, Makabe, Y.,;, Kunita, K.,. J. Org. Chem., 1988, 53, 4489.
9. Garro-Helion, F.,;, Merzouk, A.,;, Guibé, F.,. J. Org. Chem., 1993, 58, 6109.
10. Trost, B. M.,;, Spagnol, M. D.,. J. Chem. Soc., Perkin Trans. 1, 1995, 2083.
11. Mukherjee, S.,;, List, B.,. J. Am. Chem. Soc., 2007, 129, 11336.
12. Zhao, X.,;, Liu, D.,;, Guo, H.,;, Liu, Y.,;, Zhang, W.,. J. Am. Chem. Soc., 2011, 133, 19354.
13. Trost, B. M.,;, Keinan, E.,. J. Org. Chem., 1980, 45, 2741.
14. Bricout, H.,;, Carpentier, J.-F.,;, Mortreux, A.,. Chem. Commun., 1997, 33, 1393.
15. Pawlas, J.,;, Nakao, Y.,;, Kawatsura, M.,;, Hartwig, J. F.,. J. Am. Chem. Soc., 2002, 124, 3669.
16. Watson, I. D. G.,;, Yudin, A. K.,. J. Am. Chem. Soc., 2005, 127, 17516.
17. For the formation of C-S bonds, see:, Kunakova, R. V.,;, Gaisin, R. L.,;, Sirazova, M. M.,;, Dzhemilev, U. M.,. Izv. Akad. Nauk SSSR Ser. Khim., 1983, 32, 157.
18. Li, M.-B.,;, Wang, Y.,;, Tian, S.-K.,. Angew. Chem., Int. Ed., 2012, 51, 2968.
19. Wu, X.-S.,;, Chen, Y.,;, Li, M.-B.,;, Zhou, M.-G.,;, Tian, S.-K.,. J. Am. Chem. Soc., 2012, 134, 14694.
20. Li, M.-B.,;, Li, H.,;, Wang, J.,;, Liu, C.-R.,;, Tian, S.-K.,. Chem. Commun., 2013, 49, 8190.
21. Ma, X.-T.,;, Wang, Y.,;, Dai, R.-H.,;, Liu, C.-R.,;, Tian, S.-K.,. J. Org. Chem., 2013, 78, 11071.
22. Wu, X.-S.,;, Zhou, M.-G.,;, Chen, Y.,;, Tian, S.-K.,. Asian J. Org. Chem., 2014, 3, 711.
23. Wang, T.-T.,;, Wang, F.-X.,;, Yang, F.-L.,;, Tian, S.-K.,. Chem. Commun., 2014, 50, 3802.
24. Wang, Y.,;, Xu, J.-K.,;, Gu, Y.,;, Tian, S.-K.,. Org. Chem. Front., 2014, 1, 812.
25. Schenck, T. G.,;, Bosnich, B.,. J. Am. Chem. Soc., 1985, 107, 2058.
26. Liu, C.-R.,;, Li, M.-B.,;, Yang, C.-F.,;, Tian, S.-K.,. Chem. Eur. J., 2009, 15, 793.
27. Liu, C.-R.,;, Li, M.-B.,;, Cheng, D.-J.,;, Yang, C.-F.,;, Tian, S.-K.,. Org. Lett., 2009, 11, 2543.
28. Yang, B.-L.,;, Tian, S.-K.,. Chem. Commun., 2010, 46, 6180.
29. Liu, C.-R.,;, Yang, F.-L.,;, Jin, Y.-Z.,;, Ma, X.-T.,;, Cheng, D.-J.,;, Li, N.,;, Tian, S.-K.,. Org. Lett., 2010, 12, 3832.
30. Yang, C.-F.,;, Wang, J.-Y.,;, Tian, S.-K.,. Chem. Commun., 2011, 47, 8343.
31. Weng, Z.-T.,;, Li, Y.,;, Tian, S.-K.,. J. Org. Chem., 2011, 76, 8095.
32. Li, M.-B.,;, Tang, X.-L.,;, Tian, S.-K.,. Adv. Synth. Catal., 2011, 353, 1980.
33. Wu, X.-S.,;, Tian, S.-K.,. Chem. Commun., 2012, 48, 898.
34. Liu, C.-R.,;, Wang, T.-T.,;, Qi, Q.-B.,;, Tian, S.-K.,. Chem. Commun., 2012, 48, 10913.
35. Tian, Y.,;, Sui, Y.,;, Gu, Y.,;, Tian, S.-K.,. Adv. Synth. Catal., 2012, 354, 3475.
36. Tang, X.-L.,;, Wu, Z.,;, Li, M.-B.,;, Gu, Y.,;, Tian, S.-K.,. Eur. J. Org. Chem., 2012, 4107.
37. Li, H.-H.,;, Zhang, X.,;, Jin, Y.-H.,;, Tian, S.-K.,. Asian J. Org. Chem., 2013, 2, 290.
38. Gu, Y.,;, Tian, S.-K.,. Synlett, 2013, 24, 1170.
39. Hayashi, T.,;, Yamamoto, A.,;, Ito, Y.,;, Nishioka, E.,;, Miura, H.,;, Yanagi, K.,. J. Am. Chem. Soc., 1989, 111, 6301.
40. Yamazaki, A.,;, Achiwa, K.,. Tetrahedron: Asymmetry, 1995, 6, 51.
41. Togni, A.,;, Burckhardt, U.,;, Gramlich, V.,;, Pregosin, P. S.,;, Salzmann, R.,. J. Am. Chem. Soc., 1996, 118, 1031.
42. Burckhardt, U.,;, Baumann, M.,;, Togni, A.,. Tetrahedron: Asymmetry, 1997, 8, 155.
43. Jin, M.-J.,;, Jung, J.-A.,;, Kim, S.-H.,. Tetrahedron Lett., 1999, 40, 5197.
44. Malone, Y. M.,;, Guiry, P. J.,. J. Organomet. Chem., 2000, 603, 110.
45. You, S.-L.,;, Zhu, X.-Z.,;, Luo, Y.-M.,;, Hou, X.-L.,;, Dai, L.-X.,. J. Am. Chem. Soc., 2001, 123, 7471.
46. You, S.-L.,;, Hou, X.-L.,;, Dai, L.-X.,. J. Organomet. Chem., 2001, 637-639, 762.
47. Delapierre, G.,;, Brunel, J. M.,;, Constantieux, T.,;, Buono, G.,. Tetrahedron: Asymmetry, 2001, 12, 1345.
48. Pàmies, O.,;, van Strijdonck, G. P. F.,;, Diéguez, M.,;, Deerenberg, S.,;, Net, G.,;, Ruiz, A.,;, Claver, C.,;, Kamer, P. C. J.,;, van Leeuwen, P. W. N. M.,. J. Org. Chem., 2001, 66, 8867.
49. Mancheño, O. G.,;, Priego, J.,;, Cabrera, S.,;, Arrayás, R. G.,;, Llamas, T.,;, Carretero, J. C.,. J. Org. Chem., 2003, 68, 3679.
50. Zhao, D.,;, Sun, J.,;, Ding, K.,. Chem. Eur. J., 2004, 10, 5952.
51. Pakulski, Z.,;, Demchuk, O. M.,;, Frelek, J.,;, Luboradzki, R.,;, Pietrusiewicz, K. M.,. Eur. J. Org. Chem., 2004, 3913.
52. Faller, J. W.,;, Wilt, J. C.,. Org. Lett., 2005, 7, 633.
53. Welter, C.,;, Dahnz, A.,;, Brunner, B.,;, Streiff, S.,;, Dubon, P.,;, Helmchen, G.,. Org. Lett., 2005, 7, 1239.
54. Leitner, A.,;, Shekhar, S.,;, Pouy, M. J.,;, Hartwig, J. F.,. J. Am. Chem. Soc., 2005, 127, 15506.
55. Nemoto, T.,;, Fukuyama, T.,;, Yamamoto, E.,;, Tamura, S.,;, Fukuda, T.,;, Matsumoto, T.,;, Akimoto, Y.,;, Hamada, Y.,. Org. Lett., 2007, 9, 927.
56. Yamashita, Y.,;, Gopalarathnam, A.,;, Hartwig, J. F.,. J. Am. Chem. Soc., 2007, 129, 7508.
57. Birkholz, M.-N.,;, Dubrovina, N. V.,;, Shuklov, I. A.,;, Holz, J.,;, Paciello, R.,;, Waloch, C.,;, Breitc, B.,;, B?rner, A.,. Tetrahedron: Asymmetry, 2007, 18, 2055.
58. Castillo, A. B.,;, Favier, I.,;, Teuma, E.,;, Castillõn, S.,;, Godard, C.,;, Aghmiz, A.,;, Claver, C.,;, Gõmez, M.,. Chem. Commun., 2008, 6197.
59. Kato, M.,;, Nakamura, T.,;, Ogata, K.,;, Fukuzawa, S.,. Eur. J. Org. Chem., 2009, 5232.
60. Yuan, H.,;, Zhou, Z.,;, Xiao, J.,;, Liang, L.,;, Dai, L.,. Tetrahedron: Asymmetry, 2010, 21, 1874.
61. Panossian, A.,;, Fernández-Pérez, H.,;, Popa, D.,;, Vidal-Ferran, A.,. Tetrahedron: Asymmetry, 2010, 21, 2281.
62. Wang, Y.,;, Vaismaa, M. J. P.,;, Hämäläinen, A. M.,;, Tois, J. E.,;, Franzén, R.,. Tetrahedron: Asymmetry, 2011, 22, 524.
63. Liu, Z.,;, Cao, Z.,;, Du, H.,. Org. Biomol. Chem., 2011, 9, 5369.
64. Sun, Y.-W.,;, Jiang, J.-J.,;, Zhao, M.-X.,;, Wang, F.-J.,;, Shi, M.,. J. Organomet. Chem., 2011, 696, 2850.
65. Wang, Y.,;, Vaismaa, M. J. P.,;, Rissanen, K.,;, Franzén, R.,. Eur. J. Org. Chem., 2012, 1569.
66. Evans, P. A.,;, Robinson, J. E.,;, Nelson, J. D.,. J. Am. Chem. Soc., 1999, 121, 6761.
67. Ozawa, F.,;, Okamoto, H.,;, Kawagishi, S.,;, Yamamoto, S.,;, Minami, T.,;, Yoshifuji, M.,. J. Am. Chem. Soc., 2002, 124, 10968.
68. Mukherjee, P.,;, Widenhoefer, R. A.,. Org. Lett., 2011, 13, 1334.
69. Geng, W.,;, Zhang, W.-X.,;, Hao, W.,;, Xi, Z.,. J. Am. Chem. Soc., 2012, 134, 20230.
70. Xie, Y.,;, Hu, J.,;, Wang, Y.,;, Xia, C.,;, Huang, H.,. J. Am. Chem. Soc., 2012, 134, 20613.
71. Xie, Y.,;, Hu, J.,;, Xie, P.,;, Qian, B.,;, Huang, H.,. J. Am. Chem. Soc., 2013, 135, 18327.