Preparation of conjugated 1,3-enynes by Rh(iii)-catalysed alkynylation of alkenes via C-H activation

Chemical Communications

Volumn 50, Issue 34, 2014, Pages 4459-4461

  Collins, Karl D ^a   Lied, Fabian ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; BENZAMIDE DERIVATIVE; CARBON; ENYNE DERIVATIVE; HYDROGEN; IODINE; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; RHODIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYNYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CONJUGATION; CONTROLLED STUDY; NUCLEAR MAGNETIC RESONANCE; SILYL DEPROTECTION METHOD; SONOGASHIRA REACTION; SYNTHESIS;

EID: 84897528132     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01141d     Document Type: Article

References (75)

1. F. Diederich, P. J. Stang and R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005
2. J. P. Brand, J. Waser, Chem. Soc. Rev. 2012 41 4165
3. E. Negishi, L. Anastasia, Chem. Rev. 2003 103 1979
4. R. R. Tykwinski, Angew. Chem., Int. Ed. 2003 42 1566
5. R. Chinchilla, C. Nájera, Chem. Rev. 2014 114 1783
6. I. A. Meretina, B. I. Ionin and J. C. Tebby, Alkynes in Cycloadditions, Wiley-Blackwell, New Jersey, 2013
7. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001 40 2004-2021
8. I. J. S. Fairlamb, Angew. Chem., Int. Ed. 2004 43 1048
9. C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002 102 813
10. V. Mamane, P. Hannen, A. Fürstner, Chem. - Eur. J. 2004 10 4556
11. G. C. Lloyd-Jones, Org. Biomol. Chem. 2003 1 215
12. B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001 101 2067
13. S. T. Diver, A. J. Giessert, Chem. Rev. 2004 104 1317
14. L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006 348 2271
15. A. Lumbroso, M. L. Cooke, B. Breit, Angew. Chem., Int. Ed. 2013 52 1890
16. X. Zeng, Chem. Rev. 2013 113 6864
17. J.-R. Kong, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2006 128 718
18. K. M. Miller, T. Luanphaisarnnont, C. Molinaro, T. K. Jamison, J. Am. Chem. Soc. 2004 126 4130
19. H. Li, P. J. Walsh, J. Am. Chem. Soc. 2005 127 8355
20. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011 40 4740
21. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011 40 5068
22. J. L. Bras, J. Muzart, Chem. Rev. 2011 111 1170
23. L. Ackermann, Chem. Rev. 2011 111 1315
24. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011 40 1885
25. C. S. Yeung, V. M. Dong, Chem. Rev. 2011 111 1215
26. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem., Int. Ed. 2012 51 8960
27. M. C. White, Science 2012 335 807
28. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012 45 788
29. S. R. Neufeldt, M. S. Sanford, Acc. Chem. Res. 2012 45 936
30. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem., Int. Ed. 2012 51 10236
31. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013 5 369
32. L. Ackermann, Acc. Chem. Res. 2014 47 281
33. J. He, M. Wasa, K. S. L. Chan, J.-Q. Yu, J. Am. Chem. Soc. 2013 135 3387
34. S. H. Kim, S. Chang, Org. Lett. 2010 12 1868
35. I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007 129 7742
36. S. H. Kim, J. Yoon, S. Chang, Org. Lett. 2011 13 1474
37. F. Shibahara, Y. Dohke, T. Murai, J. Org. Chem. 2012 77 5381
38. M. Tobisu, Y. Ano, N. Chatani, Org. Lett. 2009 11 3250
39. L. Yang, L. Zhao, C.-J. Li, Chem. Commun. 2010 46 4184
40. Y. Gu, X. Wang, Tetrahedron Lett. 2009 50 763
41. S. H. Kim, S. H. Park, S. Chang, Tetrahedron 2012 68 5162
42. Y. Ano, M. Tobisu, N. Chatani, Synlett 2012 2763
43. C. Feng, T.-P. Loh, Angew. Chem., Int. Ed. 2014 53 2722
44. F. Xie, Z. Qi, S. Yu, X. Li, J. Am. Chem. Soc. 2014 10.1021/ja501910e
45. T. Satoh, M. Miura, Chem. - Eur. J. 2010 16 11212
46. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2011 45 814
47. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012 41 3651
48. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012 45 31
49. S. Chiba, Chem. Lett. 2012 41 1554
50. V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, J. T. Bolz, A. J. Simonsen, J. Org. Chem. 1996 61 6547
51. J. P. Brand, J. Charpentier, J. Waser, Angew. Chem., Int. Ed. 2009 48 9346
52. J. P. Brand, C. Chevalley, J. Waser, Beilstein J. Org. Chem. 2011 7 565
53. J. P. Brand, D. Fernández González, S. Nicolai, J. Waser, Chem. Commun. 2011 47 102
54. J. P. Brand, J. Waser, Angew. Chem., Int. Ed. 2010 49 7304
55. J. P. Brand, J. Waser, Org. Lett. 2012 14 744
56. D. Fernández González, J. P. Brand, J. Waser, Chem. - Eur. J. 2010 16 9457
57. D. Fernández González, J. P. Brand, R. Mondière, J. Waser, Adv. Synth. Catal. 2013 355 1631
58. R. Frei, J. Waser, J. Am. Chem. Soc. 2013 135 9620
59. Y. Li, J. P. Brand, J. Waser, Angew. Chem., Int. Ed. 2013 52 6743
60. Y. Li, J. Waser, Beilstein J. Org. Chem. 2013 9 1763
61. S. Nicolai, S. Erard, D. Fernández González, J. Waser, Org. Lett. 2010 12 384
62. G. L. Tolnai, S. Ganss, J. P. Brand, J. Waser, Org. Lett. 2013 15 112
63. F. Xie, Z. Qi, X. Li, Angew. Chem., Int. Ed. 2014 52 11862
64. K. D. Collins, F. Glorius, Nat. Chem. 2013 5 597
65. K. D. Collins, F. Glorius, Tetrahedron 2013 69 7817
66. K. D. Collins, A. Rühling, F. Lied, F. Glorius, Chem. - Eur. J. 2014 10.1002/chem.201304508
67. K. D. Collins, A. Rühling, F. Glorius, Nat. Protoc. 2014 10.1038/nprot.2014.076
68. I. Churcher, Nat. Chem. 2013 5 554
69. N. Kuhl, N. Schröder, F. Glorius, Org. Lett. 2013 15 3860
70. H. Wang, B. Beiring, D.-G. Yu, K. D. Collins, F. Glorius, Angew. Chem., Int. Ed. 2013 52 12430
71. D.-T. D. Tang, K. D. Collins, J. B. Ernst, F. Glorius, Angew. Chem., Int. Ed. 2014 53 1809
72. H. G. Lee, P. J. Milner, S. L. Buchwald, Org. Lett. 2013 15 5602
73. S. C. Cullen, S. Shekhar, N. K. Nere, J. Org. Chem. 2013 78 12194
74. P. J. Stang, Chem. Rev. 1996 96 1123
75. M. Ochiai, M. Kunishima, Y. Nagao, K. Fuji, M. Shiro, E. Fujita, J. Am. Chem. Soc. 1986 108 8281