Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides

Angewandte Chemie - International Edition

Volumn 54, Issue 51, 2015, Pages 15525-15529

  Adcock, Holly V ^a   Chatzopoulou, Elli ^a   Davies, Paul W ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

carbenes; cyclopropanation; gold; nitrogen heterocycles; ynamides

Indexed keywords

CATALYSIS; CYCLIZATION; GOLD; NITROGEN; ORGANIC COMPOUNDS; SCAFFOLDS;

CARBENES; CATALYZED SYNTHESIS; CYCLOPROPANATION; MOLECULAR COMPLEXITY; NITROGEN HETEROCYCLES; PYRIDINE DERIVATIVES; STRUCTURE REACTIVITY; YNAMIDES;

SYNTHESIS (CHEMICAL);

EID: 84955184496     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201507167     Document Type: Article

References (104)

1. F. Lovering, Med. Chem. Commun. 2013, 4, 515;
2. F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752.
3. For selected reviews, see:
4. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
5. A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410;
6. Angew. Chem. 2007, 119, 3478;
7. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
8. R. Dorel, A. M. Echavarren, Chem. Rev. 2015, 115, 9028;
9. P. W. Davies, M. Garzõn, Asian J. Org. Chem. 2015, 4, 694.
10. For reviews on ynamides, see:
11. K. A. DeKorver, H. Li, A. G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, R. P. Hsung, Chem. Rev. 2010, 110, 5064;
12. G. Evano, A. Coste, K. Jouvin, Angew. Chem. Int. Ed. 2010, 49, 2840;
13. Angew. Chem. 2010, 122, 2902;
14. X.-N. Wang, H.-S. Yeom, L.-C. Fang, S. He, Z.-X. Ma, B. L. Kedrowski, R. P. Hsung, Acc. Chem. Res. 2014, 47, 560.
15. For the synthesis of ynamides, see:
16. Y. S. Zhang, R. P. Hsung, M. R. Tracey, K. C. M. Kurtz, E. L. Vera, Org. Lett. 2004, 6, 1151;
17. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833;
18. A. Coste, G. Karthikeyan, F. Couty, G. Evano, Angew. Chem. Int. Ed. 2009, 48, 4381;
19. Angew. Chem. 2009, 121, 4445;
20. S. J. Mansfield, C. D. Campbell, M. W. Jones, E. A. Anderson, Chem. Commun. 2015, 51, 3316.
21. For examples of reactions with π-systems, see:
22. S. Couty, C. Meyer, J. Cossy, Angew. Chem. Int. Ed. 2006, 45, 6726;
23. Angew. Chem. 2006, 118, 6878;
24. F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509;
25. A. S. K. Hashmi, M. Rudolph, J. W. Bats, W. Frey, F. Rominger, T. Oeser, Chem. Eur. J. 2008, 14, 6672;
26. S. Kramer, Y. Odabachian, J. Overgaard, M. Rottländer, F. Gagosz, T. Skrydstrup, Angew. Chem. Int. Ed. 2011, 50, 5090;
27. Angew. Chem. 2011, 123, 5196; for examples of reactions with oxidants, see:
28. P. W. Davies, A. Cremonesi, N. Martin, Chem. Commun. 2011, 47, 379;
29. C.-W. Li, K. Pati, G.-Y. Lin, S. A. Sohel, H.-H. Hung, R.-S. Liu, Angew. Chem. Int. Ed. 2010, 49, 9891;
30. Angew. Chem. 2010, 122, 10087;
31. D. Vasu, H.-H. Hung, S. Bhunia, S. A. Gawade, A. Das, R.-S. Liu, Angew. Chem. Int. Ed. 2011, 50, 6911;
32. Angew. Chem. 2011, 123, 7043;
33. K.-B. Wang, R.-Q. Ran, S.-D. Xiu, C-.Y. Li, Org. Lett. 2013, 15, 2374;
34. R. Liu, G. N. Winston-McPherson, Z.-Y. Yang, X. Zhou, W. Song, I. A. Guzei, X. Xu, W. Tang, J. Am. Chem. Soc. 2013, 135, 8201;
35. M. D. Santos, P. W. Davies, Chem. Commun. 2014, 50, 6001;
36. L. Li, C. Shu, B. Zhou, Y.-F. Yu, X.-Y. Xiao, L.-W. Ye, Chem. Sci. 2014, 5, 4057; for examples of reactions with nitrenoids, see:
37. C. Li, L. Zhang, Org. Lett. 2011, 13, 1738;
38. P. W. Davies, A. Cremonesi, L. Dumitrescu, Angew. Chem. Int. Ed. 2011, 50, 8931;
39. Angew. Chem. 2011, 123, 9093;
40. Y. Tokimizu, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2014, 16, 3138;
41. M. Garzõn, P. W. Davies, Org. Lett. 2014, 16, 4850;
42. A.-H. Zhou, Q. He, C. Shu, Y.-F. Yu, S. Liu, T. Zhao, W. Zhang, X. Lu, L.-W. Ye, Chem. Sci. 2015, 6, 1265;
43. L. Zhu, Y. Yu, Z. Mao, X. Huang, Org. Lett. 2015, 17, 30.
44. H. V. Adcock, T. Langer, P. W. Davies, Chem. Eur. J. 2014, 20, 7262.
45. For a review on insertion into C-X σ-bonds, see:, H. V. Adcock, P. W. Davies, Synthesis 2012, 44, 3401.
46. For impressive super-acid-mediated cationic cascades of aromatic ynamides with insertion at unfunctionalized benzylic positions, see:, C. Theunissen, B. Métayer, N. Henry, G. Compain, J. Marrot, A. Martin-Mingot, S. Thibaudeau, G. Evano, J. Am. Chem. Soc. 2014, 136, 12528.
47. For reviews on C-H insertion, see:
48. L. Wang, J. Xiao, Adv. Synth. Catal. 2014, 356, 1137;
49. M. C. Haibach, D. Seidel, Angew. Chem. Int. Ed. 2014, 53, 5010;
50. Angew. Chem. 2014, 126, 5110;
51. J. Xie, C. Pan, A. Abdukader, C. Zhu, Chem. Soc. Rev. 2014, 43, 5245.
52. 2) bonds from alkynes under Au catalysis, see:
53. I. D. Jurberg, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 2010, 132, 3543;
54. J. Barluenga, R. Sigüeiro, R. Vicente, A. Ballesteros, M. Tomás, M. A. Rodríguez, Angew. Chem. Int. Ed. 2012, 51, 10377;
55. Angew. Chem. 2012, 124, 10523;
56. M. M. Hansmann, M. Rudolph, F. Rominger, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2013, 52, 2593;
57. Angew. Chem. 2013, 125, 2653;
58. L. Ye, Y. Wang, D. H. Aue, L. Zhang, J. Am. Chem. Soc. 2012, 134, 31;
59. G. Cera, M. Chiarucci, F. Dosi, M. Bandini, Adv. Synth. Catal. 2013, 355, 2227; for their formation under Pt catalysis, see:
60. 3) bonds from alkynes under Au catalysis, see:
61. G. Lemière, V. Gandon, N. Agenet, J.-P. Goddard, A. deKozak, C. Aubert, L. Fensterbank, M. Malacria, Angew. Chem. Int. Ed. 2006, 45, 7596;
62. Angew. Chem. 2006, 118, 7758; for their formation under Pt catalysis, see:
63. D. Vasu, A. Das, R.-S. Liu, Chem. Commun. 2010, 46, 4115.
64. For a review, see:
65. D. Qian, J. Zhang, Chem. Soc. Rev. 2015, 44, 677.
66. A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. Int. Ed. 2004, 43, 6545;
67. Angew. Chem. 2004, 116, 6707.
68. CCDC 1410362 (3 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
69. For recent examples of gold-catalyst-controlled pathway divergence, see:
70. C.-D. Wang, Y.-F. Hsieh, R.-S. Liu, Adv. Synth. Catal. 2014, 356, 144;
71. L.-Y. Mei, Y. Mei, X.-Y. Tang, M. Shi, J. Am. Chem. Soc. 2015, 137, 8131;
72. N. Morita, A. Yasuda, M. Shibata, S. Ban, Y. Hashimoto, I. Okamoto, O. Tamura, Org. Lett. 2015, 17, 2668;
73. W. Rao, D. Susanti, B. J. Ayers, P. W. H. Chan, J. Am. Chem. Soc. 2015, 137, 6350;
74. G. Xu, C. Zhu, W. Gu, J. Li, J. Sun, Angew. Chem. Int. Ed. 2015, 54, 883;
75. Angew. Chem. 2015, 127, 897; for a general review, see:
76. J. Mahatthananchai, A. M. Dumas, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 10954;
77. Angew. Chem. 2012, 124, 11114.
78. This result could potentially be due to an aryl-ynamide interaction; see:, C. Wang, X. Xie, J. Liu, Y. Liu, Y. Li, Chem. Eur. J. 2015, 21, 559.
79. E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066;
80. Angew. Chem. 2012, 124, 3120.
81. At a 0.27 M concentration, 1 f was consumed in 70min; 72 % of [D] 1 f was consumed in 6h.
82. For indene formation by alkyne insertion into benzylic C-H bonds under Pt/Ru catalysis, see:
83. M. Tobisu, H. Nakai, N. Chatani, J. Org. Chem. 2009, 74, 5471;
84. S. Yang, Z. Li, X. Jian, C. He, Angew. Chem. Int. Ed. 2009, 48, 3999;
85. Angew. Chem. 2009, 121, 4059;
86. G. B. Bajracharya, N. K. Pahadi, I. D. Gridnev, Y. Yamamoto, J. Org. Chem. 2006, 71, 6204; for Au catalysis, see:
87. P. Morán-Poladura, E. Rubio, J. M. González, Angew. Chem. Int. Ed. 2015, 54, 3052;
88. Angew. Chem. 2015, 127, 3095.
89. Neither substrate proved reactive in the polycyclization. This result is consistent with a larger angle between the reaction centers in A / A ′ (Scheme5) for a thiophene scaffold, and destabilization of the putative cation B by the pyridinyl group.
90. For an accelerating effect of substitution adjacent to the hydride-donor site, see:, K. Mori, T. Kawasaki, S. Sueoka, T. Akiyama, Org. Lett. 2010, 12, 1732.
91. The congested intermediates B / B ′ are drawn as if they were planar, but would be formed in atropisomeric conformations owing to the stereoelectronic requirements of a sigmatropic or through-space hydride shift. For a study on the role of rotational barriers in reaction pathways, see:, O. N. Faza, C. S. Lõpez, A. R. deLera, J. Org. Chem. 2011, 76, 3791.
92. Y. Horino, T. Yamamoto, K. Ueda, S. Kuroda, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 2809;
93. S. Bhunia, S. Ghorpade, D. B. Huple, R.-S. Liu, Angew. Chem. Int. Ed. 2012, 51, 2939;
94. Angew. Chem. 2012, 124, 2993.
95. For a review, see:, R. Dorel, A. M. Echavarren, J. Org. Chem. 2015, 80, 7321.
96. For N-allyl ynesulfonamide aza-Claisen reactions, see:
97. K. A. DeKorver, T. D. North, R. P. Hsung, Synlett 2010, 16, 2397;
98. K. A. Dekorver, R. P. Hsung, A. G. Lohse, Y. Zhang, Org. Lett. 2010, 12, 1840;
99. K. A. DeKorver, W. L. Johnson, Y. Zhang, R. P. Hsung, H. Dai, J. Deng, A. G. Lohse, Y.-S. Zhang, J. Org. Chem. 2011, 76, 5092;
100. K. A. Dekorver, R. P. Hsung, A. W.-Z. Song, X.-N. Wang, M. C. Walton, Org. Lett. 2012, 14, 3214;
101. X.-N. Wang, G. N. Winston-McPherson, M. C. Walton, Y. Zhang, R. P. Hsung, K. A. DeKorver, J. Org. Chem. 2013, 78, 6233;
102. Y. Zhang, K. A. Dekorver, A. G. Lohse, Y.-S. Zhang, J. Huang, R. P. Hsung, Org. Lett. 2009, 11, 899; the allylic inversion in 14 b is consistent with the results of these studies.
103. L. Sun, Y. Zhu, P. Lu, Y. Wang, Org. Lett. 2013, 15, 5894.
104. X.-Z. Shu, K.-G. Ji, S.-C. Zhao, Z.-J. Zheng, J. Chen, L. Lu, X.-Y. Lui, Y.-M. Liang, Chem. Eur. J. 2008, 14, 10556.