Palladium-catalyzed insertion of an allene into an aminal: Aminomethylamination of allenes by C-N bond activation

Angewandte Chemie - International Edition

Volumn 53, Issue 28, 2014, Pages 7272-7276

  Hu, Jianhua ^a   Xie, Yinjun ^b   Huang, Hanmin ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

allenes; aminals; C N activation; diamines; palladium

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; PALLADIUM;

ALLENES; ALLYLPALLADIUM COMPLEXES; AMINALS; ATOM ECONOMIC; BOND ACTIVATION; DIAMINES; MECHANISTIC STUDIES; PALLADIUM-CATALYZED;

HYDROCARBONS;

4 AMINOBUTYRIC ACID; ALKADIENE; CARBON; COORDINATION COMPOUND; METHYLAMINE; NITROGEN; PALLADIUM; PROPADIENE;

AMINATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM;

ALKADIENES; AMINATION; CARBON; CATALYSIS; COORDINATION COMPLEXES; GAMMA-AMINOBUTYRIC ACID; METHYLAMINES; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM;

EID: 84903768993     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403774     Document Type: Article

References (76)

1. F. Cohen, L. E. Overman, J. Am. Chem. Soc. 2001, 123, 10782
2. R. J. Bergeron, Y. Feng, W. R. Weimar, J. S. McManis, H. Dimova, C. Porter, B. Raisler, O. Phanstiel, J. Med. Chem. 1997, 40, 1475
3. W. P. Hems, M. Groarke, A. Zanotti-Gerosa, G. A. Grasa, Acc. Chem. Res. 2007, 40, 1340
4. J.-C. Kizirian, Chem. Rev. 2008, 108, 140
5. G. F. Busscher, F. P. J. T. Rutjes, F. L. vanDelft, Chem. Rev. 2005, 105, 775.
6. V. Constantinou-Kokotou, G. Kokotos, Org. Prep. Proced. Int. 1994, 26, 599
7. C. G. Espino, P. M. Wehn, J. Chow, J. DuBois, J. Am. Chem. Soc. 2001, 123, 6935
8. B. Merla, N. Risch, Synthesis 2002, 1365
9. X.-L. Hou, Y.-M. Luo, K. Yuan, L.-X. Dai, J. Chem. Soc. Perkin Trans. 1 2002, 12, 1487
10. C.-H. Zhao, L. Liu, D. Wang, Y.-J. Chen, Eur. J. Org. Chem. 2006, 2977
11. J. Vesely, I. Ibrahem, R. Rios, G.-L. Zhao, Y. Xu, A. Cõrdova, Tetrahedron Lett. 2007, 48, 2193
12. T. Kurokawa, M. Kim, J. DuBois, Angew. Chem. Int. Ed. 2009, 48, 2777
13. Angew. Chem. 2009, 121, 2815
14. M. Martjuga, S. Belyakov, E. Liepinsh, E. Suna, J. Org. Chem. 2011, 76, 2635
15. C. D. Weatherly, J. W. Rigoli, J. M. Schomaker, Org. Lett. 2012, 14, 1704.
16. D. Lucet, T. LeGall, C. Mioskowski, Angew. Chem. Int. Ed. 1998, 37, 2580
17. Angew. Chem. 1998, 110, 2724
18. S. DeJong, D. G. Nosal, D. J. Wardrop, Tetrahedron 2012, 68, 4067; for selected recent examples, see
19. E. L. Ingalls, P. A. Sibbald, W. Kaminsky, F. E. Michael, J. Am. Chem. Soc. 2013, 135, 8854
20. H. Zhang, W. Pu, T. Xiong, Y. Li, X. Zhou, K. Sun, Q. Liu, Q. Zhang, Angew. Chem. Int. Ed. 2013, 52, 2529
21. Angew. Chem. 2013, 125, 2589
22. K. Muñiz, C. Martinez, J. Org. Chem. 2013, 78, 2168
23. R. G. Cornwall, B. Zhao, Y. Shi, Org. Lett. 2013, 15, 796
24. B. W. Turnpenny, S. R. Chemler, Chem. Sci. 2014, 5, 1786.
25. R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem. Int. Ed. 2004, 43, 1679
26. Angew. Chem. 2004, 116, 1711
27. M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. Int. Ed. 2006, 45, 2254
28. Angew. Chem. 2006, 118, 2312
29. M. Terada, C. K. Sorimachi, Angew. Chem. Int. Ed. 2009, 48, 2553
30. Angew. Chem. 2009, 121, 2591
31. G. Dagousset, F. Drouet, G. Masson, J. Zhu, Org. Lett. 2009, 11, 5546.
32. J. P. Wolfe, Eur. J. Org. Chem. 2007, 571
33. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
34. K. H. Jensen, M. S. Sigman, Org. Biomol. Chem. 2008, 6, 4083
35. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981.
36. J.-E. Bäckvall, in Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed., (Eds.: A. deMeijere, F. Diederich,), Wiley-VCH, Hoboken, 2004, p. 479
37. J.-E. Bäckvall, S. E. Bystroem, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619
38. J.-E. Bäckvall, J.-E. Nystroem, R. E. Nordberg, J. Am. Chem. Soc. 1985, 107, 3676
39. J.-E. Bäckvall, J. O. Vaagberg, J. Org. Chem. 1988, 53, 5695
40. G. L. J. Bar, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2005, 127, 7308
41. H. Du, W. Yuan, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2007, 129, 11688
42. H. Du, B. Zhao, Y. Shi, J. Am. Chem. Soc. 2008, 130, 8590
43. K. B. Urkalan, M. S. Sigman, Angew. Chem. Int. Ed. 2009, 48, 3146
44. Angew. Chem. 2009, 121, 3192
45. B. Zhao, H. Du, S. Cui, Y. Shi, J. Am. Chem. Soc. 2010, 132, 3523
46. K. H. Jensen, J. D. Webb, M. S. Sigman, J. Am. Chem. Soc. 2010, 132, 17471
47. E. W. Werner, K. B. Urkalan, M. S. Sigman, Org. Lett. 2010, 12, 2848
48. E. J. Alexanian, C. Lee, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 7690
49. G. Liu, S. S. Stahl, J. Am. Chem. Soc. 2006, 128, 7179
50. D. Kalyani, M. S. Sanford, J. Am. Chem. Soc. 2008, 130, 2150
51. Y. Li, D. Song, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 2962
52. A. Wang, H. Jiang, H. Chen, J. Am. Chem. Soc. 2009, 131, 3846
53. S. Qiu, T. Xu, J. Zhou, Y. Guo, G. Liu, J. Am. Chem. Soc. 2010, 132, 2856.
54. B. Cazes, Pure Appl. Chem. 1990, 62, 1867
55. R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067
56. J. A. Marshall, Chem. Rev. 2000, 100, 3163
57. X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535
58. "Carbopalladation of Allenes":, S. Ma, in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.:, E.-I. Negishi, A. deMeijere,), Wiley-Interscience, New York, 2002
59. R. W. Bates, V. Satcharoen, Chem. Soc. Rev. 2002, 31, 12
60. M. A. Tius, Acc. Chem. Res. 2003, 36, 284
61. L. K. Sydnes, Chem. Rev. 2003, 103, 1133
62. S. Ma, Acc. Chem. Res. 2003, 36, 701
63. L.-L. Wei, H. Xiong, R. P. Hsung, Acc. Chem. Res. 2003, 36, 773
64. L. Brandsma, N. A. Nedolya, Synthesis 2004, 735
65. S. Ma, Chem. Rev. 2005, 105, 2829
66. M. Jeganmohan, C.-H. Cheng, Chem. Commun. 2008, 3101.
67. Y. Xie, J. Hu, Y. Wang, C. Xia, H. Huang, J. Am. Chem. Soc. 2012, 134, 20613
68. Y. Xie, J. Hu, P. Xie, B. Qian, H. Huang, J. Am. Chem. Soc. 2013, 135, 18327.
69. CCDC983572 (3 aa) and 983573 (complex II) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
70. H. L. Dryden, G. M. Webber, R. R. Burtner, J. A. Cella, J. Org. Chem. 1961, 26, 3237
71. W. F. Johns, J. Org. Chem. 1963, 28, 1856.
72. H. Kato, T. Ishigame, N. Oshima, N. Hoshiya, K. Shimawaki, M. Arisawa, S. Shuto, Adv. Synth. Catal. 2011, 353, 2676.
73. V. Vecchietti, G. D. Clarke, R. Colle, G. Giardina, G. Petrone, M. Sbacchi, J. Med. Chem. 1991, 34, 2624; for the synthesis of 2,9-diamino- and 2-amino-8-carbamoxyl-4-hydroxy-alkanoic acid/amide, see
74. V. Rastti, H. Rüeger, J. K. Maibaum, R. Mah, M. Grütter, N. C. Cohen, U.S. Patent 5719141, 1998; for the production and use of similar amine compounds, see
75. N. Suzuki, K. Kato, S. Takekawa, J. Terauchi, S. Endo, U.S. Patent 6329389 B1, 2001.
76. T. Bai, L. Xue, P. Xue, J. Zhu, H. H. Sung, S. Ma, I. D. Wiliams, Z. Lin, G. Jia, Organometallics 2008, 27, 2614.