Suzuki cross-coupling reaction of benzylic halides with arylboronic acids in the presence of a tetraphosphine/palladium catalyst

Synlett

Volumn , Issue 11, 2003, Pages 1668-1672

  Chahen, Ludovic ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Arylboronic acids; Benzylic halides; Catalysis; Palladium; Tetraphosphine

Indexed keywords

BORONIC ACID DERIVATIVE; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; SUZUKI REACTION;

EID: 0041910967     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40994     Document Type: Article

References (31)

1. For reviews on the palladium-catalysed Suzuki cross-coupling reactions see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
2. For reviews on the palladium-catalysed Suzuki cross-coupling reactions see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
3. For reviews on the palladium-catalysed Suzuki cross-coupling reactions see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
4. For reviews on the palladium-catalysed Suzuki cross-coupling reactions see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (c) Suzuki, A. J. Organomet. Chem. 2002, 653, 83. (d) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
5. (a) Beller, M.; Fischer, H.; Herrmann, W.A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848.
6. (b) Albisson, D.A.; Bedford, R.B.; Lawrence, S.E.; Scully, P.N. Chem. Commun. 1998, 2095.
7. (c) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901.
8. (d) Wolfe, J.P.; Buchwald, S.L. Angew. Chem., Int. Ed. 1999, 38, 2413.
9. (e) Wolfe, J.P.; Singer, R.A.; Yang, B.H.; Buchwald, S.L.J. Am. Chem. Soc. 1999, 121, 9550.
10. For examples of Suzuki reactions with benzylic halides: (a) Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (b) Pernia, G.J.; Kilburn, J.D.; Essex, J.W.; Mortishire-Smith, R.J.; Rowley, M.J. Am. Chem. Soc. 1996, 118, 10220. (c) Chowdhury, S.; Georghiou, P.E. Tetrahedron Lett. 1999, 40, 7599. (d) Juteau, H.; Gareau, Y.; Labelle, M.; Sturino, C.F.; Sawyer, N.; Tremblay, N.; Lamontagne, S.; Carrière, M.-C.; Denis, D.; Metters, K.M. Bioorg. Med. Chem. 2001, 9, 1977. (e) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
11. For examples of Suzuki reactions with benzylic halides: (a) Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (b) Pernia, G.J.; Kilburn, J.D.; Essex, J.W.; Mortishire-Smith, R.J.; Rowley, M.J. Am. Chem. Soc. 1996, 118, 10220. (c) Chowdhury, S.; Georghiou, P.E. Tetrahedron Lett. 1999, 40, 7599. (d) Juteau, H.; Gareau, Y.; Labelle, M.; Sturino, C.F.; Sawyer, N.; Tremblay, N.; Lamontagne, S.; Carrière, M.-C.; Denis, D.; Metters, K.M. Bioorg. Med. Chem. 2001, 9, 1977. (e) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
12. For examples of Suzuki reactions with benzylic halides: (a) Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (b) Pernia, G.J.; Kilburn, J.D.; Essex, J.W.; Mortishire-Smith, R.J.; Rowley, M.J. Am. Chem. Soc. 1996, 118, 10220. (c) Chowdhury, S.; Georghiou, P.E. Tetrahedron Lett. 1999, 40, 7599. (d) Juteau, H.; Gareau, Y.; Labelle, M.; Sturino, C.F.; Sawyer, N.; Tremblay, N.; Lamontagne, S.; Carrière, M.-C.; Denis, D.; Metters, K.M. Bioorg. Med. Chem. 2001, 9, 1977. (e) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
13. For examples of Suzuki reactions with benzylic halides: (a) Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (b) Pernia, G.J.; Kilburn, J.D.; Essex, J.W.; Mortishire-Smith, R.J.; Rowley, M.J. Am. Chem. Soc. 1996, 118, 10220. (c) Chowdhury, S.; Georghiou, P.E. Tetrahedron Lett. 1999, 40, 7599. (d) Juteau, H.; Gareau, Y.; Labelle, M.; Sturino, C.F.; Sawyer, N.; Tremblay, N.; Lamontagne, S.; Carrière, M.-C.; Denis, D.; Metters, K.M. Bioorg. Med. Chem. 2001, 9, 1977. (e) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
14. For examples of Suzuki reactions with benzylic halides: (a) Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1985, 26, 5997. (b) Pernia, G.J.; Kilburn, J.D.; Essex, J.W.; Mortishire-Smith, R.J.; Rowley, M.J. Am. Chem. Soc. 1996, 118, 10220. (c) Chowdhury, S.; Georghiou, P.E. Tetrahedron Lett. 1999, 40, 7599. (d) Juteau, H.; Gareau, Y.; Labelle, M.; Sturino, C.F.; Sawyer, N.; Tremblay, N.; Lamontagne, S.; Carrière, M.-C.; Denis, D.; Metters, K.M. Bioorg. Med. Chem. 2001, 9, 1977. (e) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
15. For examples of Suzuki reactions with ethyl bromoacetate or cinnamyl bromide derivatives, see: (a) Moreno-Manas,M.; Pajuelo,F.; Pleixats,R.J. Org. Chem. 1995, 60, 2396. (b) Cortes,J.; Moreno-Manas,M.; Pleixats,R. Eur.J. Org. Chem. 2000, 239. (c) Gooßen,L.J. Chem. Commun. 2001, 669. (d) Liu,X.-X.; Deng,M.-Z. Chem. Commun. 2002, 622.
16. For examples of Suzuki reactions with ethyl bromoacetate or cinnamyl bromide derivatives, see: (a) Moreno-Manas,M.; Pajuelo,F.; Pleixats,R.J. Org. Chem. 1995, 60, 2396. (b) Cortes,J.; Moreno-Manas,M.; Pleixats,R. Eur.J. Org. Chem. 2000, 239. (c) Gooßen,L.J. Chem. Commun. 2001, 669. (d) Liu,X.-X.; Deng,M.-Z. Chem. Commun. 2002, 622.
17. For examples of Suzuki reactions with ethyl bromoacetate or cinnamyl bromide derivatives, see: (a) Moreno-Manas,M.; Pajuelo,F.; Pleixats,R.J. Org. Chem. 1995, 60, 2396. (b) Cortes,J.; Moreno-Manas,M.; Pleixats,R. Eur.J. Org. Chem. 2000, 239. (c) Gooßen,L.J. Chem. Commun. 2001, 669. (d) Liu,X.-X.; Deng,M.-Z. Chem. Commun. 2002, 622.
18. For examples of Suzuki reactions with ethyl bromoacetate or cinnamyl bromide derivatives, see: (a) Moreno-Manas,M.; Pajuelo,F.; Pleixats,R.J. Org. Chem. 1995, 60, 2396. (b) Cortes,J.; Moreno-Manas,M.; Pleixats,R. Eur.J. Org. Chem. 2000, 239. (c) Gooßen,L.J. Chem. Commun. 2001, 669. (d) Liu,X.-X.; Deng,M.-Z. Chem. Commun. 2002, 622.
19. For examples of coupling of arylboronic acids with allylacetate, see: Bouyssi,D.; Gerusz,V.; Balme,G. Eur.J. Org. Chem. 2002, 2445.
20. For a review on the synthesis of polypodal diphenylphosphine ligands, see: Laurenti,D.; Santelli,M. Org. Prep. Proced. Int. 1999, 31, 245.
21. Laurenti,D.; Feuerstein,M.; Pèpe,G.; Doucet,H.; Santelli,M.J. Org. Chem. 2001, 66, 1633.
22. Feuerstein,M.; Doucet,H.; Santelli,M.J. Org. Chem. 2001, 66, 5923.
23. (a) Feuerstein,M.; Laurenti,D.; Bougeant,C.; Doucet,H.; Santelli,M. Chem. Commun. 2001, 325.
24. (b) Feuerstein,M.; Laurenti,D.; Doucet,H.; Santelli,M. Synthesis 2001, 2320.
25. (c) Feuerstein,M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 5659.
26. (d) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 6667.
27. (e) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001, 1458.
28. (f) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli, M. Synlett 2002, 1807.
29. (g) Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2003, 1091.
30. 3): 8 = 7.59 (d, J = 8.3 Hz, 2 H, Ar), 7.29 (d, J = 8.3 Hz, 2 H, Ar), 7.11 (d, J = 8.6 Hz, 2 H, Ar), 6.88 (d, J = 8.6 Hz, 2 H, Ar), 4.00 (s, 2 H, CH2), 3.82 (s, 3 H, OMe).
31. +].