Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes

Organic Letters

Volumn 16, Issue 11, 2014, Pages 3024-3027

  Cornelissen, Loïc ^a   Lefrancq, Maxime ^a   Riant, Olivier ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84902086154     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501140p     Document Type: Article

References (39)

1. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2193
2. Curtis-Long, M. J.; Aye, Y. Chem.-Eur. J. 2009, 15, 5402-5416
3. Sore, H. F.; Galloway, W. R. J. D.; Spring, D. R. Chem. Soc. Rev. 2012, 41, 1845-1866
4. Nakao, Y.; Hiyama, T. Chem. Soc. Rev. 2011, 40, 4893-4901 and references cited therein
5. Denmark, S. E.; Baird, J. D. Chem.-Eur. J. 2006, 12, 4954-4963 and references cited therein
6. Taguchi, H.; Miyashita, H.; Tsubouchi, A.; Takeda, T. Chem. Commun. 2002, 2218-2219
7. Tsubouchi, A.; Onishi, K.; Takeda, T. J. Am. Chem. Soc. 2006, 128, 14268-14269
8. Tsubouchi, A.; Matsuda, H.; Kira, T.; Takeda, T. Chem. Lett. 2009, 38, 1180-1181
9. Tsubouchi, A.; Enatsu, S.; Kanno, R.; Takeda, T. Angew. Chem., Int. Ed. 2010, 49, 7089-7091
10. Tsubouchi, A.; Muramatsu, D.; Takeda, T. Angew. Chem., Int. Ed. 2013, 52, 12719-12722
11. Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 4138-4139
12. Lee, K.-S.; Hoveyda, A. H. J. Org. Chem. 2009, 74, 4455-4462
13. Gurung, S. K.; Thapa, S.; Vangala, A. S.; Giri, R. Org. Lett. 2013, 15, 5378-5381
14. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922
15. Brandsma, L. Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques; Elsevier: Oxford, 2004.
16. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017
17. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834-871
18. Commerçon, A.; Normant, J. F.; Villieras, J. Tetrahedron 1980, 36, 1215-1221
19. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980
20. Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1992, 33, 3647-3650
21. Sorg, A.; Brückner, R. Angew. Chem., Int. Ed. 2004, 43, 4523-4526
22. Hoshi, M.; Kawamura, N.; Shirakawa, K. Synthesis 2006, 1961-1970
23. Wang, S.; Wang, M.; Wang, L.; Wang, B.; Li, P.; Yang, J. Tetrahedron 2011, 67, 4800-4806
24. Cornelissen, L.; Vercruysse, S.; Sanhadji, A.; Riant, O. Eur. J. Org. Chem. 2014, 35-38
25. Berthon-Gelloz, G.; Schumers, J.-M.; De Bo, G.; Markó, I. E. J. Org. Chem. 2008, 73, 4190-4197
26. De Bo, G.; Berthon- Gelloz, G.; Tinant, B.; Markó, I. E. Organometallics 2006, 25, 1881-1890
27. Dierick, S.; Markó, I. E. Personal communications with their permission.
28. Synthesis of α-vinylsiloxanes: Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2005, 127, 17644-17655
29. Synthesis of β-(Z)-vinylsiloxanes: Faller, J. W.; D'Alliessi, D. G. Organometallics 2002, 21, 1743-1746
30. Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem. Soc. 1995, 117, 5166-5167
31. Handy, C. J.; Lam, Y.-F.; DeShong, P. J. Org. Chem. 2000, 65, 3542-3543
32. Thongsornkleeb, C.; Danhaiser, R. L. J. Org. Chem. 2005, 70, 2364
33. Xu, H.-D.; Zhang, R.-W.; Li, X.; Huang, S.; Tang, W.; Hu, W.-H. Org. Lett. 2013, 15, 840-843
34. Anastasia, L.; Negishi, E. Org. Lett. 2001, 3, 3111-3113
35. Negishi, E.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597-1600
36. Bohlmann, F.; Thefeld, W.; Zdero, C. Chem. Ber. 1970, 103, 2245-2251
37. Taniguchi, M.; Uchio, Y.; Yasumoto, K.; Kusumi, T.; Ooi, T. Chem. Pharm. Bull. 2008, 56, 378-382
38. Akiyama, T.; Takada, K.; Oikawa, T.; Matsuura, N.; Ise, Y.; Okada, S.; Matsunaga, S. Tetrahedron 2013, 69, 6560-6564
39. Organ, M. G.; Ghasemi, H. J. Org. Chem. 2004, 69, 695-700