Selective arylation of 1,1-disubstituted olefins using a biphenyl-based phosphine in Heck coupling reactions

Tetrahedron Letters

Volumn 50, Issue 39, 2009, Pages 5470-5473

  Nadri, Shirin ^a   Joshaghani, Mohammad ^a,b   Rafiee, Ezzat ^a,b  

^a RAZI UNIVERSITY   (Iran)

^b Kermanshah Oil Refining Company   (Iran)

Author keywords

1,1 Disubstituted olefins; Biphenyl based phosphine; C C Coupling; Heck reaction

Indexed keywords

2 DIPHENYLPHOSPHINO 2' METHYLBIPHENYL; ALKENE DERIVATIVE; BIPHENYL DERIVATIVE; BROMINE DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HECK REACTION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 68349144437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.052     Document Type: Article

References (34)

1. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581
2. Heck R.F., and Nolley J.P. J. Org. Chem. 37 (1972) 2320-2322
3. Morales-Morales D., Grause C., Kasaoka K., Redón R., Cramer R.E., and Jensen C.M. Inorg. Chim. Acta 300-302 (2000) 958-963
4. Beller M., and Riermeier T.H. Eur. J. Inorg. Chem. (1998) 29-35
5. Zhou P., Li Y., Sun P., Zhou L., and Bao J. Chem. Commun. (2007) 1418-1420
6. Caló V., Nacci A., Monopoli A., Detomaso A., and Iliade P. Organometallics 22 (2003) 4193-4197
7. Trejos A., Sävmarker J., Schlummer S., Datta G.K., Nilsson P., and Larhed M. Tetrahedron 64 (2008) 8746-8751
8. Zawisza A.M., Ganchegui B., González I., Bouquillon S., Roglans A., Hénin F., and Muzart J. J. Mol. Catal. A: Chem. 283 (2008) 140-145
9. Berthiol F., Doucet H., and Santelli M. Tetrahedron 62 (2006) 4372-4383
10. Watanabe T., Hayashi K., Yoshimatsu S., and Sakai K. J. Med. Chem. 23 (1980) 50-59
11. Buchanan J.G., Hill D.G., and Wightman R.H. Tetrahedron 51 (1995) 6033-6050
12. Young W.R., Aviram A.R., and Cox J. J. Am. Chem. Soc. 94 (1972) 3976-3981
13. Kagechika H., Himi T., Namikawa K., Kawachi E., Hashimoto Y., and Shudo K. J. Med. Chem. 32 (1989) 1098-1108
14. Littke A.F., and Fu G.C. J. Org. Chem. 64 (1999) 10-11
15. Shaughnessy K.H., Kim P., and Hartwig J.F. J. Am. Chem. Soc. 121 (1999) 2123-2132
16. Whitcombe N.J., Hii K.K., and Gibson S.E. Tetrahedron 57 (2001) 7449-7476
17. Bedford R.B. Chem. Commun. (2003) 1787-1796
18. Hartwig J.F. In: Negishi E. (Ed). HandBook on Organopalladium Chemistry for Organic Synthesis (2002), Wiley Interscience, New York 1051-1096 and references therein
19. Old D.W., Wolfe J.P., and Buchwald S.L. J. Am. Chem. Soc. 120 (1998) 9722-9723
20. Vorogushin A.V., Huang X.H., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 8146-8149
21. Wolfe J.P., Wagaw S., Marcox J.F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
22. Billingsley K.L., Anderson K.W., and Buchwald S.L. Angew. Chem., Int. Ed. 45 (2006) 3484-3488
23. Yin J., Rainka M.P., Zhang X.-X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 1162-1163
24. Walker S.D., Barder T.E., Martinelli J.R., and Buchwald S.L. Angew. Chem., Int. Ed. 43 (2004) 1871-1876
25. Barder T.E., Walker S.D., and Martinelli J.R. J. Am. Chem. Soc. 127 (2005) 4685-4696
26. Barder T.E. J. Am. Chem. Soc. 128 (2006) 898-904
27. Barder T.E., and Buchwald S.L. J. Am. Chem. Soc. 129 (2007) 12003-12010
28. Barder T.E., Biscoe M.R., and Buchwald S.L. Organometallics 26 (2007) 2183-2192
29. Joshaghani M., Faramarzi E., Rafiee E., Daryanavard M., Xiao B., and Baillie C. J. Mol. Catal. A: Chem. 259 (2006) 35-40
30. Joshaghani M., Faramarzi E., Rafiee E., Daryanavard M., Xiao J., and Baillie C. J. Mol. Catal. A: Chem. 273 (2007) 310-315
31. Joshaghani M., Daryanavard M., Rafiee E., Xiao J., and Baillie C. Tetrahedron Lett. 48 (2007) 2025-2027
32. Joshaghani M., Daryanavard M., Rafiee E., and Nadri Sh. J. Organomet. Chem. 693 (2008) 3135-3140
33. Nadri Sh., Joshaghani M., and Rafiee E. Appl. Catal. A: Gen. 362 (2009) 163-168
34. 1H NMR spectroscopy.