Remarkable regioselectivity in microwave-enhanced palladium-catalyzed allylation reaction involving allyltrifluoroborates and aryl halides

Tetrahedron Letters

Volumn 50, Issue 37, 2009, Pages 5201-5204

  Al Masum, Mohammad ^a   Alam, Shahrina ^a  

^a TENNESSEE STATE UNIVERSITY   (United States)

Author keywords

Central carbon addition; Microwave heating; New catalyst; Potassium allyltrifluoroborates

Indexed keywords

ALLYL COMPOUND; ALLYLTRIFLUOROBORATE DERIVATIVE; CARBON; CYCLOPROPANE; HALIDE; METHYL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; GAS CHROMATOGRAPHY; ISOMERIZATION; MASS SPECTROMETRY; MICROWAVE COOKING; REACTION ANALYSIS;

EID: 67650902487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.134     Document Type: Article

References (29)

1. Molander G.A., and Ham J. Org. Lett. 8 (2006) 2031
2. Molander G.A., and Figueroa R. Aldrichchim. Acta 38 (2005) 49
3. Molander G.A., and Felix L.A. J. Org. Chem. 70 (2005) 3950
4. Tremblay-Morin J.-P., Raeppel S., and Gaudette F. Tetrahedron Lett. 45 (2004) 3471
5. Molander G.A., and Ribagorda M. J. Am. Chem. Soc. 125 (2003) 11148
6. Quach T.D., and Batey R.A. Org. Lett. 5 (2003) 1381
7. Molander G.A., and Bernardi C.R. J. Org. Chem. 67 (2002) 8424
8. Molander G.A., Katona B.W., and Machrouhi F. J. Org. Chem. 67 (2002) 8416
9. Pucheault M., Darses S., and Genet J.-P. Eur. J. Org. Chem. (2002) 3552
10. Molander G.A., and Rivero M.R. Org. Lett. 4 (2002) 107
11. Batey R.A., Thadani A.N., Smil D.V., and Lough A. Synthesis (2000) 990
12. Darses S., Michauld G., and Genet J.-P. Eur. J. Org. Chem. (1999) 1875
13. Darses S., and Genet J.-P. Chem. Rev. 108 (2008) 288
14. For recent reviews:. Godleski S.A. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford 585
15. Hegedus L. In: Schlosser M. (Ed). Organometallics in Synthesis (1994), Wiley, New York 385-459
16. In: Tsuji J. (Ed). Palladium Reagents and Catalysis (1995), Wiley, New York
17. Kabalka G.W., and Al-Masum M. Org. Lett. 8 (2006) 11
18. Kabalka G.W., Dadush E., and Al-Masum M. Tetrahedron Lett. 47 (2006) 7459
19. Kabalka G.W., Al-Masum M., Mereddy A.R., and Dadush E. Tetrahedron Lett. 47 (2006) 1133
20. Arvela R.K., Leadbeater N.E., Mack T.L., and Kormos C.M. Tetrahedron Lett. 47 (2006) 217
21. Kabalka G.W., and Al-Masum M. Tetrahedron Lett. 46 (2005) 6329
22. Sebelius S., Olsson V.J., Wallner O.A., and Szabo K.J. J. Am. Chem. Soc. 128 (2006) 8150
23. Yamamoto Y., Takada S., and Miyaura N. Chem. Lett. 35 (2006) 704
24. Vedejs E., Chapman R.W., Fields S.C., Lin S., and Schrimpf M.R. J. Org. Chem. 60 (1995) 3024
25. Batey R.A., Thadani A.N., and Smil D.V. Tetrahedron Lett. 40 (1999) 4289
26. 2 4a-4j was 5:1. In case of 4-methyliodobenzene, 2j, the ratio was 3:2 (Table 1, entry 10). The endo- and exo-products were unable to be separated by chromatography. For simplification, exo-products were not shown.
27. Hegedus L.S., Darlington W.H., and Russell C.E. J. Org. Chem. 45 (1980) 5193
28. + 197. Found: 197.
29. + 152. Found: 152.