Rhodium(iii)-catalyzed olefinic C–H alkynylation of enamides at room temperature

Chemical Communications

Volumn 50, Issue 69, 2014, Pages 9865-9868

  Feng, Chao ^a   Feng, Daming ^a   Loh, Teck Peng ^a,b  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENE DERIVATIVE; AMIDE; CARBON 13; HALOGEN; RHODIUM; TRANSITION ELEMENT;

ALKYNYLATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; DESILYLATION; ELECTROPHILICITY; METHYLATION; OLEFINATION; OLEFINIC ALKYNYLATION; ROOM TEMPERATURE; SONOGASHIRA REACTION; STEREOSPECIFICITY; STOICHIOMETRY; TRIFLUOROMETHYLATION; X RAY DIFFRACTION;

EID: 84905499395     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04072d     Document Type: Article

References (57)

1. L. Brandsma, Y. A. Heus-Kloos, R. Van Der Heiden, and H. D. Verkruijsse, Preparative Acetylenic Chemistry, Elsevier, New York, 2nd edn, 1988
2. L. Brandsma, S. F. Vasilevsky, and H. D. Verkruijsse, Application of Transition Metal Catalysts in Organic Synthesis, Springer-Verlag, New York, 1998
3. E. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979
4. C. E. Castro, R. D. Stephens, J. Org. Chem. 1963, 28, 2163
5. A. O. King, N. Okukado, E. Negishi, J. Chem. Soc. Chem. Commun. 1977, 42, 683
6. A. O. King, E. Negishi, F. J. Villani, Jr. A. Silveira, Jr. J. Org. Chem. 1978, 43, 358
7. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
8. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
9. L.-M. Xu, Z. Yang, Z.-J. Shi, Chem. Soc. Rev. 2010, 39, 712
10. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792
11. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094
12. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242
13. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467
14. P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. Int. Ed. 2000, 39, 2632
15. K. Kobayashi, M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 8528
16. I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742
17. F. Besslievre, S. Piguel, Angew. Chem. Int. Ed. 2009, 48, 9553
18. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522
19. T. de Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512
20. A. Dudnik, V. Gevorgyan, Angew. Chem. Int. Ed. 2010, 49, 2096
21. J. K. Stille, J. H. Simpson, J. Am. Chem. Soc. 1987, 109, 2138
22. W. J. Scott, G. T. Crisp, J. K. Stille, J. Am. Chem. Soc. 1984, 106, 4630
23. I. Perez, J. Perez Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155
24. S. Hyuga, Y. Chiba, N. Yamashina, S. Hara, A. Suzuki, Chem. Lett. 1987, 1757
25. E. Negishi, F. Liu, D. Choueiry, M. M. Mohamud, A. Silveira, Jr. M. Reeves, J. Org. Chem. 1996, 61, 8325
26. X. Lu, X. Huang, S. Ma, Tetrahedron Lett. 1992, 33, 2535
27. R. Takeuchi, K. Tanabe, S. Tanaka, J. Org. Chem. 2000, 65, 1558
28. J. A. Marshall, H. R. Chobanian, M. M. Yanik, Org. Lett. 2001, 3, 4107
29. C. G. Bates, P. Saejueng, D. Venkataraman, Org. Lett. 2004, 6, 1441
30. T. Jeffery, Synthesis. 1987, 70
31. Y. Wen, A. Wang, H. Jiang, S. Zhu, L. Huang, Tetrahedron Lett. 2011, 52, 5736
32. S.-K. Kung, K.-Y. Jung, C.-H. Park, S.-B. Jang, Tetrahedron Lett. 1995, 36, 8047
33. D. R. Carbery, Org. Biomol. Chem. 2008, 6, 3455
34. H. Zhou, Y. H. Xu, W. J. Chung, T.-P. Loh, Angew. Chem. Int. Ed. 2009, 48, 5355
35. H. Zhou, W. J. Chung, Y. H. Xu, T.-P. Loh, Chem. Commun. 2009, 3472
36. Y. H. Xu, Y. K. Chok, T.-P. Loh, Chem. Sci. 2011, 2, 1822
37. C. Feng, T.-P. Loh, Chem. Sci. 2012, 3, 3458
38. S. Pankajakshan, Y. H. Xu, J. K. Cheng, M. T. Low, T.-P. Loh, Angew. Chem. Int. Ed. 2012, 51, 5701
39. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
40. Y. Su, M. Zhao, K. Han, G. Song, X. Li, Org. Lett. 2010, 12, 5462
41. S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585
42. H. Wang, B. Beiring, D.-G. Yu, K. D. Collins, F. Glorius, Angew. Chem. Int. Ed. 2013, 52, 12430
43. T. K. Hyster, T. Rovis, Chem. Commun. 2011, 47, 11846
44. C. Feng, T.-P. Loh, Angew. Chem. Int. Ed. 2014, 53, 2722
45. F. Xie, Z. Qi, S. Yu, X. Li, J. Am. Chem. Soc. 2014, 136, 4780
46. K. D. Collins, F. Lied, F. Glorius, Chem. Commun. 2014, 50, 4459
47. Y. H. Xu, J. Lu, T.-P. Loh, J. Am. Chem. Soc. 2009, 131, 1372
48. C. Feng, T.-P. Loh, J. Am. Chem. Soc. 2010, 132, 17710
49. J. Zhang, T.-P. Loh, Chem. Commun. 2012, 48, 11232
50. C. Feng, T.-P. Loh, Angew. Chem. Int. Ed. 2013, 52, 12414
51. C. Feng, T.-P. Loh, Chem. Commun. 2011, 47, 10458
52. C. Feng, D. Feng, T.-P. Loh, Org. Lett. 2013, 15, 3670
53. J. P. Brand, J. Charpentier, J. Waser, Angew. Chem. Int. Ed. 2009, 48, 9346
54. J. P. Brand, J. Waser, Angew. Chem. Int. Ed. 2010, 49, 7304
55. Y. Li, J. P. Brand, J. Waser, Angew. Chem. Int. Ed. 2013, 52, 6743
56. Z. Wang, X. Li, Y. Huang, Angew. Chem. Int. Ed. 2013, 52, 14219
57. CCDC. http://xlink.rsc.org/?ccdc=980753&msid=c4cc04072d