Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1130-1135

  Du, Wei ^a   Gu, Qiangshuai ^a   Li, Zhongliang ^a   Yang, Dan ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; PALLADIUM COMPOUNDS;

CHEMICAL EQUATIONS; DIRECTING GROUPS; FIVE-MEMBERED RINGS; FUNCTIONALIZATIONS; MECHANISM STUDIES; OPTIMIZED CONDITIONS; RATE DETERMINING STEP; TANDEM REACTION;

PALLADIUM;

BORON; PALLADIUM;

ALKYLATION; ARTICLE; CATALYST; CYCLIZATION; HALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84921830184     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5102739     Document Type: Article

References (91)

1. (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
2. (b) Dyker, G. Handbook of C - H Transformations ; Wiley-VCH: Weinheim, 2005.
3. (c) Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749-823.
4. (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834.
5. (b) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318-5365.
6. (c) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238.
7. (d) Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949-957.
8. (e) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074-1086.
9. (f) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115.
10. (g) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169.
11. (h) Ackermann, L. Chem. Rev. 2011, 111, 1315-1345.
12. (i) Mousseau, J. J.; Charette, A. B. Acc. Chem. Res. 2012, 46, 412-424.
13. (j) Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761.
14. (k) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2011, 45, 788-802.
15. (l) Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Synthesis 2012, 44, 1778-1791.
16. (m) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726-11743.
17. (a) Godula, K.; Sames, D. Science 2006, 312, 67-72.
18. (b) Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061-5074.
19. (c) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242-3272.
20. (d) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654-2672.
21. (e) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902. Also see ref 2f, g, l, and m.
22. (a) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953-956.
23. (b) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
24. (c) Bellina, F.; Rossi, R. Chem. Rev. 2009, 110, 1082-1146.
25. (d) Burtoloso, A. C. B. Synlett 2009, 320-327.
26. (e) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676-707.
27. (f) Ankner, T.; Cosner, C. C.; Helquist, P. Chem.-Eur. J. 2013, 19, 1858-1871.
28. (a) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289-2292.
29. (b) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462-3465.
30. (c) Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 2373-2375.
31. (d) Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266-3267.
32. (e) Mousseau, J. J.; Larivee, A.; Charette, A. B. Org. Lett. 2008, 10, 1641-1643.
33. (f) Burton, P. M.; Morris, J. A. Org. Lett. 2010, 12, 5359-5361.
34. (g) Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095-1097.
35. (h) Song, G.; Su, Y.; Gong, X.; Han, K.; Li, X. Org. Lett. 2011, 13, 1968-1971.
36. (i) Liu, J.-Y.; Niu, H.-Y.; Wu, S.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2012, 48, 9723-9725.
37. (j) Piou, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2012, 51, 11561-11565.
38. (k) Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763-2766.
39. (l) Piou, T.; Bunescu, A.; Wang, Q.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 12385-12389.
40. (m) Zhou, M.-B.; Wang, C.-Y.; Song, R.-J.; Liu, Y.; Wei, W.-T.; Li, J.-H. Chem. Commun. 2013, 49, 10817-10819.
41. (n) Zhao, D.; Zhu, M.-X.; Wang, Y.; Shen, Q.; Li, J.-X. Org. Biomol. Chem. 2013, 11, 6246-6249.
42. (a) Baudoin, O.; Herrbach, A.; Guéritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736-5740.
43. (b) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154-13155.
44. (c) Giri, R.; Maugel, N.; Foxman, B. M.; Yu, J.-Q. Organometallics 2008, 27, 1667-1670.
45. (d) Chaumontet, M.; Piccardi, R.; Audic, N.; Hitce, J.; Peglion, J.-L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157-15166.
46. (e) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886-9887.
47. (f) Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414-3417.
48. (g) Rousseaux, S.; Davi, M.; Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706-10716.
49. (h) He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192-5196.
50. (i) Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984-12986.
51. (j) Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076-19079.
52. (k) Pierre, C.; Baudoin, O. Org. Lett. 2011, 13, 1816-1819.
53. (l) Pan, J.; Su, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 8647-8651.
54. (m) Guyonnet, M.; Baudoin, O. Org. Lett. 2011, 14, 398.
55. (n) Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507-7510.
56. (o) McNally, A.; Haffemayer, B.; Collins, B. S. L.; Gaunt, M. J. Nature 2014, 510, 129-133.
57. (a) Catellani, M.; Motti, E.; Ghelli, S. Chem. Commun. 2000, 2003-2004.
58. (b) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634-12635.
59. (c) Liron, F.; Knochel, P. Tetrahedron Lett. 2007, 48, 4943-4946.
60. (d) Kim, H. S.; Gowrisankar, S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3858-3861.
61. (e) Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190-7191.
62. (f) Huang, Q.; Larock, R. C. Tetrahedron Lett. 2009, 50, 7235-7238.
63. (g) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965-3972.
64. (h) Mu, X.; Wu, T.; Wang, H.-y.; Guo, Y.-l.; Liu, G. J. Am. Chem. Soc. 2011, 134, 878-881.
65. (i) Wu, T.; Mu, X.; Liu, G. Angew. Chem., Int. Ed. 2011, 50, 12578-12581.
66. (j) Pedroni, J.; Boghi, M.; Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 9064-9067.
67. (k) Mao, J.; Zhang, S.-Q.; Shi, B.-F.; Bao, W. Chem. Commun. 2014, 50, 3692-3694.
68. (a) Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130-3131.
69. (b) He, W.; Yip, K.-T.; Zhu, N.-Y.; Yang, D. Org. Lett. 2009, 11, 5626-5628.
70. (c) Yip, K.-T.; Yang, D. Org. Lett. 2011, 13, 2134-2137.
71. (d) Yip, K.-T.; Yang, D. Chem.-Asian J. 2011, 6, 2166-2175.
72. (e) Xing, D.; Yang, D. Org. Lett. 2013, 15, 4370-4373.
73. (a) Welstead, W. J.; Stauffer, H. F.; Sancilio, L. F. J. Med. Chem. 1974, 17, 544-547.
74. (b) Kam, T.-S.; Yoganathan, K.; Chuah, C.-H. Tetrahedron Lett. 1995, 36, 759-762.
75. (c) Kam, T.-S.; Lim, K.-H.; Yoganathan, K.; Hayashi, M.; Komiyama, K. Tetrahedron 2004, 60, 10739-10745.
76. (a) Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773-781.
77. (b) Hartmann, L.; Witte, L. Alkaloides: Chemical and Biological Perspectives ; Elsevier Science: Oxford, 1995; Vol. 9.
78. (c) Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723-2796.
79. (d) Tomasz, M. Chem. Biol. 1995, 2, 575-579.
80. (a) Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570-10705.
81. (b) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759-1762.
82. Fluck, E. The Chemistry of Phosphine; Springer: Berlin, Heidelberg, 1973.
83. We observed phosphine oxide by LC-MS analysis.
84. 3 provided identical yields, but we chose the former due to its lower price.
85. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692-10705.
86. See Table S9 in the Supporting Information.
87. (a) Singleton, D. A.; Thomas, A. A. J. Am. Chem. Soc. 1995, 117, 9357-9358.
88. (b) Frantz, D. E.; Singleton, D. A.; Snyder, J. P. J. Am. Chem. Soc. 1997, 119, 3383-3384.
89. 13C KIE is depicted in the Supporting Information.
90. Substrates without angular substitutions were found to give monocyclized products. See the Supporting Information for detail.
91. The involvement of a radical intermediate can be excluded, as addition of a stoichiometic amount of TEMPO had little e ffect on the cyclization.