A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides

Chemical Communications

Volumn 50, Issue 45, 2014, Pages 6001-6004

  Santos, Mickaèl Dos ^a   Davies, Paul W ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBON; GOLD; SULFONIUM DERIVATIVE; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 84899955119     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01059k     Document Type: Article

References (57)

1. J. S. Clark, Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry, Oxford University Press, Oxford, 2002
2. Sulfur Mediated Rearrangements: Topics in Current Chemistry, ed. E. Schaumann, vol. 275, Springer, Heidelberg, 2007
3. W. Kirmse, M. Kapps, Chem. Ber., 1968, 101, 994
4. M. P. Doyle, W. H. Tamblyn, V. Bagheri, J. Org. Chem., 1981, 46, 5094
5. M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998
6. A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev., 1997, 97, 2341
7. D. M. Hodgson, F. Y. T. M. Pierard, P. A. Stupple, Chem. Soc. Rev., 2001, 30, 50
8. M. S. Holzwarth, I. Alt, B. Plietker, Angew. Chem., Int. Ed., 2012, 51, 5351
9. V. K. Aggarwal, C. L. Winn, Acc. Chem. Res., 2004, 37, 611
10. Y. Li, Z. Huang, X. Wu, P.-F. Xu, J. Jin, Y. Zhang, J. Wang, Tetrahedron, 2012, 68, 5234
11. P. W. Davies, S. J.-C. Albrecht, Chem. Commun., 2008, 238
12. P. W. Davies, S. J.-C. Albrecht, Angew. Chem., Int. Ed., 2009, 48, 8372
13. P. W. Davies, Pure Appl. Chem., 2010, 82, 1537
14. P. W. Davies, S. J.-C. Albrecht, Synlett, 2012, 70
15. Y. Kato, K. Miki, K. F. Nishino, K. Ohe, S. Uemura, Org. Lett., 2003, 5, 2619
16. D. Yadagiri, P. Anbarasan, Chem. – Eur. J., 2013, 19, 15115
17. P. W. Davies, S. J.-C. Albrecht, G. Assanelli, Org. Biomol. Chem., 2009, 7, 1276
18. N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc., 2007, 129, 4160
19. G. Li, L. Zhang, Angew. Chem., Int. Ed., 2007, 46, 5156
20. B. Lu, Y. Li, Y. Wang, D. H. Aue, Y. Luo, L. Zhang, J. Am. Chem. Soc., 2013, 135, 8512
21. P. W. Davies, A. Cremonesi, N. Martin, Chem. Commun., 2011, 47, 379
22. P. W. Davies, A. Cremonesi, L. Dumitrescu, Angew. Chem., Int. Ed., 2011, 50, 8931
23. D. Vasu, H.-H. Hung, S. Bhunia, S. A. Gawade, A. Das, R.-S. Liu, Angew. Chem., Int. Ed., 2011, 50, 6911
24. A. Mukherjee, R. B. Dater, R. Chaudhuri, S. Bhunia, S. N. Karad, R.-S. Liu, J. Am. Chem. Soc., 2011, 133, 15372
25. S. Bhunia, C.-J. Chang, R.-S. Liu, Org. Lett., 2012, 14, 5522
26. R. B. Dateer, K. Pati, R.-S. Liu, Chem. Commun., 2012, 48, 7200
27. L.-Q. Yang, K.-B. Wang, C.-Y. Li, Eur. J. Org. Chem., 2013, 2775
28. K.-B. Wang, R.-Q. Ran, S.-D. Xiu, C.-Y. Li, Org. Lett., 2013, 15, 2374
29. 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
30. C.-W. Li, K. Pati, G.-Y. Lin, S. A. Sohel, H.-H. Hung, R.-S. Liu, Angew. Chem., Int. Ed., 2010, 49, 9891
31. C.-F. Xu, M. Xu, Y.-X. Jia, C.-Y. Li, Org. Lett., 2011, 13, 1556
32. C. Li, L. Zhang, Org. Lett., 2011, 13, 1738
33. Y. Zhang, R. P. Hsung, M. R. Tracey, K. C. M. Kurtz, E. L. Vera, Org. Lett., 2004, 6, 1151
34. A. Coste, G. Karthikeyan, F. Couty, G. Evano, Angew. Chem., Int. Ed., 2009, 48, 4381
35. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc., 2008, 130, 833
36. K. A. DeKorver, H. Li, A. G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, R. P. Hsung, Chem. Rev., 2010, 110, 5064
37. G. Evano, A. Coste, K. Jouvin, Angew. Chem., Int. Ed., 2010, 49, 2840
38. L. Ye, W. He, L. Zhang, J. Am. Chem. Soc., 2010, 132, 8550
39. L. Zhang, Acc. Chem. Res., 2014, 47, 877
40. M. Xu, T.-T. Ren, C.-Y. Li, Org. Lett., 2012, 14, 4902
41. A. S. K. Hashmi, T. Wang, S. Shi, M. Rudolph, J. Org. Chem., 2012, 77, 7761
42. D. Qian, J. Zhang, Chem. Commun., 2012, 48, 7082
43. J. Fu, H. Shang, Z. Wang, L. Chang, W. Shao, Z. Yang, Y. Tang, Angew. Chem., Int. Ed., 2013, 52, 4198
44. S. Bhunia, S. Ghorpade, D. B. Huple, R.-S. Liu, Angew. Chem., Int. Ed., 2013, 52, 4229
45. G. Henrion, T. E. J. Chavas, X. Le Goff, F. Gagosz, Angew. Chem., Int. Ed., 2013, 52, 6277
46. W. He, L. Xie, Y. Xu, J. Xiang, L. Zhang, Org. Biomol. Chem., 2012, 10, 3168
47. Y. Luo, K. Ji, Y. Li, L. Zhang, J. Am. Chem. Soc., 2012, 134, 17412
48. K. Ji, Y. Zhao, L. Zhang, Angew. Chem., Int. Ed., 2013, 52, 6508
49. L. Xie, Z. Liang, D. Yan, W. He, J. Xiang, Synlett, 2013, 1809
50. C. Wu, Z. Liang, D. Yan, W. He, J. Xiang, Synthesis, 2013, 2605
51. R. J. Mudd, P. C. Young, J. A. Jordan-Hore, G. M. Rosair, A.-L. Lee, J. Org. Chem., 2012, 77, 7633
52. D. Benitez, N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard III, F. D. Toste, Nat. Chem., 2009, 1, 482
53. T. Fukudat, R. Irie, T. Katsuki, Tetrahedron, 1999, 55, 649
54. S. Kitagaki, Y. Yanamoto, H. Okubo, M. Nakajima, S. Hashimoto, Heterocycles, 2001, 54, 623
55. Y. Nishibayashi, K. Ohe, S. Uemura, J. Chem. Soc., Chem. Commun., 1995, 1245
56. X. Zhang, Z. Qu, Z. Ma, W. Shi, X. Jin, J. Wang, J. Org. Chem., 2002, 67, 5621
57. S. J. Coles, P. A. Gale, Chem. Sci., 2012, 3, 683