Palladium-catalyzed haloallylation of aromatic ynol ethers with allyl chlorides: A highly regio- and stereoselective approach to (1E)-α- chloroenol ethers

Chemical Communications

Volumn 47, Issue 30, 2011, Pages 8682-8684

  Cai, Haiting ^a   Yuan, Zheliang ^a   Zhu, Weidong ^a   Zhu, Gangguo ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL CHLORIDE; CARBONYL DERIVATIVE; CHEMICAL COMPOUND; ETHER DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HALOALLYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 79960515956     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc13424h     Document Type: Article

References (44)

1. E.-I. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Hoboken, NJ, 2002
2. A. de Meijere and F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004, vol. 1
3. K. Kaneda F. Kawamoto Y. Fujiwara T. Imanaka S. Teranishi Tetrahedron Lett. 1974 15 1067
4. K. Kaneda T. Uchiyama Y. Fujiwara T. Imanaka S. Teranishi J. Org. Chem. 1979 44 55
5. A. N. Thadani V. H. Rawal Org. Lett. 2002 4 4317
6. A. N. Thadani V. H. Rawal Org. Lett. 2002 4 4321
7. S. Ma B. Wu S. Zhao Org. Lett. 2003 5 4429
8. S. Ma B. Wu X. Jiang J. Org. Chem. 2005 70 2588
9. J. Huang L. Zhou H. Jiang Angew. Chem., Int. Ed. 2006 45 1945
10. H. Jiang X. Liu L. Zhou Chem.-Eur. J. 2008 14 11305
11. H. Jiang C. Qiao W. Liu Chem.-Eur. J. 2010 16 10968
12. S. Ma X. Lu J. Chem. Soc., Chem. Commun. 1990 733
13. S. Ma X. Lu J. Org. Chem. 1991 56 5120
14. S. Ma G. Zhu X. Lu J. Org. Chem. 1993 58 3692
15. J.-E. Bäckvall Y. I. M. Nilsson P. G. Andersson R. G. P. Gatti J. Wu Tetrahedron Lett. 1994 35 5713
16. T. R. Hoye J. Wang J. Am. Chem. Soc. 2005 127 6950
17. G. Zhu Z. Zhang J. Org. Chem. 2005 70 3339
18. Y. Liang S. Tang X.-D. Zhang L.-Q. Mao Y.-X. Xie J. H. Li Org. Lett. 2006 8 3017
19. S. Tang Q.-F. Yu P. Peng J.-H. Li P. Zhong R.-Y. Tang Org. Lett. 2007 9 3413
20. X.-C. Huang F. Wang Y. Liang J.-H. Li Org. Lett. 2009 11 1139
21. S. Q. Ye K. Gao H. Zhou X. D. Yang J. Wu Chem. Commun. 2009 5406
22. X. Chen W. Kong H. Cai L. Kong G. Zhu Chem. Commun. 2011 47 2164
23. D. Chen Y. Cao Z. Yuan H. Cai R. Zheng L. Kong G. Zhu J. Org. Chem. 2011 76 4071
24. T. Kippo T. Fukuyama I. Ryu Org. Lett. 2010 12 4006
25. S. Ma X. Lu J. Org. Chem. 1993 58 1245
26. J.-E. Bäckvall Y. I. M. Nilsson R. G. P. Gatti Organometallics 1995 14 4242
27. N. Miyaura K. Yamada A. Suzuki Tetrahedron Lett. 1979 20 3437
28. H. Tomori J. M. Fox S. L. Buchwald J. Org. Chem. 2000 65 5334
29. K. Sonogashira Y. Tohda N. Hagihara Tetrahedron Lett. 1975 16 4467
30. D. Gelman S. L. Buchwald Angew. Chem., Int. Ed. 2003 42 5993
31. A. Takahashi Y. Kirio M. Sodeoka H. Sasai M. Shibasaki J. Am. Chem. Soc. 1989 111 643
32. M. Shindo T. Kita T. Kumagai K. Matsumoto K. Shishido J. Am. Chem. Soc. 2006 128 1062
33. J. R. DeBergh K. M. Spivey J. M. Ready J. Am. Chem. Soc. 2008 130 7828
34. B. Bourdon M. Corbet P. Fontaine P. G. Goekjian D. Gueyrard Tetrahedron Lett. 2008 49 747
35. P. Lemoine B. Daoust Tetrahedron Lett. 2008 49 6175
36. Z. Song L. Kui X. Sun L. Li Org. Lett. 2011 13 1440
37. D. J. Winternheimer R. E. Shade C. A. Merlic Synthesis 2010 2497
38. R. Tanaka S. I. Miller Tetrahedron Lett. 1971 12 1753
39. P. J. Stang K. A. Roberts J. Am. Chem. Soc. 1986 108 7125
40. M. Shindo Tetrahedron 2007 63 10
41. J. Ruan J. Xiao Acc. Chem. Res. 2011 44 10.1021/ar200053d
42. S. A. Strazisar P. T. Wolczanski J. Am. Chem. Soc. 2001 123 4728
43. Z. Zhang X. Lu Z. Xu Q. Zhang X. Han Organometallics 2001 20 3724
44. R. A. Stockland S. R. Foley R. F. Jordan J. Am. Chem. Soc. 2003 125 796