A general method for regioselective Heck arylation of electron-rich N-acyl-N-vinylamine with aryl halides

Tetrahedron Letters

Volumn 49, Issue 17, 2008, Pages 2756-2760

  Liu, Zhihua ^a   Xu, Dan ^a   Tang, Weijun ^a   Xu, Lijin ^a   Mo, Jun ^b   Xiao, Jianliang ^b  

^a RENMIN UNIVERSITY OF CHINA   (China)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALKENE; AMINE; HALIDE; N ACYL N VINYLAMINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; ELECTRON; HECK REACTION; HYDROGEN BOND;

EID: 40949101252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.144     Document Type: Article

References (33)

1. Alonso F., Beletskaya I.P., and Yus M. Tetrahedron 61 (2005) 11771-11835
2. Shibasaki M., Vogl E.M., and Ohshima T. Adv. Synth. Catal. 346 (2004) 1533-1552
3. Bedford R.B., Cazin C.S.J., and Holder D. Coord. Chem. Rev. 248 (2004) 2283-2321
4. Larhed M., and Hallberg A. In: Negishi E.-I. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley-Interscience, New York 1133
5. Beletakaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009-3066
6. Cabri W., and Candiani I. Acc. Chem. Res. 28 (1995) 2-7
7. Crisp G.T. Chem. Soc. Rev. 27 (1998) 427-436
8. Knowles J.P., and Whiting A. Org. Biomol. Chem. 5 (2007) 31-44
9. Deeth R.J., Smith A., and Brown J.M. J. Am. Chem. Soc. 126 (2004) 7144-7151
10. von Schenck H., Akermark B., and Svensson M. J. Am. Chem. Soc. 125 (2003) 3503-3508
11. von Schenck H., Akermark B., and Svensson M. Organometallics 21 (2002) 2248-2253
12. Amatore C., Godin B., Jutand A., and Lemaitre F. Organometallics 26 (2007) 1757-1761
13. Mo J., Xu L., and Xiao J. J. Am. Chem. Soc. 127 (2005) 751-760
14. Xu L., Chen W., Ross J., and Xiao J. Org. Lett. 3 (2001) 295-297
15. Hyder Z., Mo J., and Xiao J. Adv. Synth. Catal. 348 (2006) 1699-1704
16. Mo J., Xu L., Ruan J., Liu S., and Xiao J. Chem. Commun. (2006) 3591-3593
17. Park S.B., and Alper H. Org. Lett. 5 (2003) 3209-3212
18. Vallin K.S.A., Emilsson P., Larhed M., and Hallberg A. J. Org. Chem. 67 (2002) 6243-6246
19. Mo J., and Xiao J. Angew. Chem., Int. Ed. 45 (2006) 4152-4157
20. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029-3069
21. Matsubara R., Nakamura Y., and Kobayashi S. Angew. Chem., Int. Ed. 43 (2004) 1679-1681
22. Jia Y., Zhong J., Zhu S., Zhang C., and Zhou Q. Angew. Chem., Int. Ed. 46 (2007) 5565-5567
23. Kagan H.B., Langlois N., and Dang T.P. J. Organomet. Chem. 90 (1975) 353-365
24. Burk M.J., Lee J.R., and Wang Y.M. J. Am. Chem. Soc. 118 (1996) 5142-5143
25. Zhu G., Casalnuovo A.L., and Zhang X. J. Org. Chem. 63 (1998) 8100-8101
26. Savarin C.G., Boice G.N., Murry J.A., Corley E., DiMichele L., and Hughes D. Org. Lett. 8 (2006) 3903-3906
27. Harrison P., and Meek G. Tetrahedron Lett. 45 (2004) 9277-9280
28. Lindhardt A., and Skrydstrup T. J. Org. Chem. 70 (2005) 5997-6003
29. Amatore C., Godin B., Jutand A., and Lemaitre F. Organometallics 26 (2007) 1757-1761
30. Amatore C., Godin B., Jutand A., and Lemaitre F. Chem. Eur. J. 13 (2007) 2002-2011
31. Arvela R.K., Pasquini S., and Larhed M. J. Org. Chem. 72 (2007) 6390-6396
32. Yin J., and Buchwald S.L. Org. Lett. 2 (2000) 1101-1104
33. 2O calcd: 212.0950; found, 212.0955.