Synthesis and catalytic applications of sulfonate β-ketoimine and β-diimine in the Suzuki reaction in aqueous phase

Journal of Organometallic Chemistry

Volumn 693, Issue 25, 2008, Pages 3692-3696

  Guo, Xuming ^a   Zhou, Jin ^a   Li, Xiaoyan ^a   Sun, Hongjian ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Diimine; Ketoimine; Aryl boric acid; Aryl bromide; Palladium chloride; Suzuki reaction

Indexed keywords

ACIDS; INORGANIC ACIDS;

AQUEOUS PHASE; ARYL BORIC ACID; ARYL BROMIDE; CATALYTIC APPLICATIONS; CATALYTIC SYSTEMS; CROSS COUPLINGS; DIIMINE; PALLADIUM CHLORIDE; SUZUKI REACTION; SUZUKI REACTIONS;

PALLADIUM;

EID: 55349112485     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.08.038     Document Type: Article

References (35)

1. Miyaura N., Yanagi T., and Suzuki A. Syn. Commun. 11 (1981) 513
2. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
3. Stanforth S.P. Tetrahedron 54 (1998) 263
4. Suzuki A. J. Organomet. Chem. 576 (1999) 147
5. Suzuki A. J. Organomet. Chem. 653 (2002) 83
6. Miyaura N. Top. Curr. Chem. 219 (2002) 11
7. Littke A.F., and Fu G.C. Angew. Chem. Int. Ed. 41 (2002) 4176
8. Bedford R.B., Cazin C.S.J., and Holder D. Coord. Chem. Rev. 248 (2004) 2283
9. Bellina F., Carpita A., and Rossi R. Synthesis (2004) 2419
10. Frisch A.C., and Beller M. Angew. Chem. Int. Ed. 44 (2005) 674
11. Arvela R.K., Leadbeater N.E., Sangi M.S., Williams V.A., Granados P., and Singer R.D. J. Org. Chem. 70 (2005) 161
12. Gil-Moltó J., Karlström S., and Nájera C. Tetrahedron 61 (2005) 12168
13. Leadbeater N.E., and Marco M. J. Org. Chem. 68 (2003) 888
14. Blettner C.G., König W.A., Stenzel W., and Schotten T. J. Org. Chem. 64 (1999) 3885
15. Korolev D.N., and Bumagin N.A. Tetrahedron Lett. 46 (2005) 5751
16. Genet J.P., Linquist A., Blart E., Mourie's V., Savignac M., and Vaultier M. Tetrahedron Lett. 36 (1995) 1443
17. Molander G.A., and Biolatto B. J. Org. Chem. 68 (2003) 4302
18. Shaughnessy K.H., and Booth R.S. Org. Lett. 3 (2001) 2757
19. Ramesh Kumar N.S.C., Victor Paul Raj I., and Sudalai A. J. Mol. Cat. A: Chem. 269 (2007) 218
20. Chen C.L., Liu Y.H., Peng S.M., and Liu S.T. Tetrahedron Lett. 46 (2005) 521
21. Li S.H., Lin Y.J., Cao J.G., and Zhang S.B. J. Org. Chem. 72 (2007) 4067
22. Feldman J., Mclain S.J., Parthasarathy A., Marshall W.J., Calabrese J.C., and Arthur S.D. Organometallics 16 (1997) 1514
23. Wang C., Friedrich S., Younkin T.R., Li R.T., Grubbs R.H., Bansleben D.A., and Day M.W. Organometallics 17 (1998) 3149
24. Domin D., Benito-Garagorri D., Mereiter K., Fröhlich J., and Kirchner K. Organometallics 24 (2005) 3957
25. Courtin A., Tobel H.R., and Doswald P. Helv. Chim. Acta 61 (1978) 3079
26. Kanetani F., and Yamaguchi H. Bull. Chem. Soc. Jpn. 54 (1981) 3048
27. Guo X.M., Wang Q.B., Harms K., and Sun H. J. Acta Cryst. E63 (2007) m2316
28. Littke A.F., Dai C., and Fu G.C. J. Am. Chem. Soc. 122 (2000) 4020
29. Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., and Alcazar-Roman L.M. J. Org. Chem. 64 (1999) 5575
30. Shaughnessy K.H., and Booth R.S. Org. Lett. 3 (2001) 2757
31. Jeffery T. Tetrahedron Lett. 35 (1994) 3051
32. Badone D., Baroni M., Cardamone R.A., and Guzzi I.U. J. Org. Chem. 62 (1997) 7170
33. Botella L., and Náera C. Angew. Chem. Int. Ed. 41 (2002) 179
34. Weissman H., and Milstein D. Chem. Commun. (1999) 1901
35. (1) Biphenyl δ 7.59-7.57 (m, 4H), 7.44-7.40 (m, 4H), 7.35-7.30 (m, 2H). (2) 4-Methylbiphenyl δ 7.54 (d, J = 8.1 Hz, 2H), 7.45 (d, J = 8.1 Hz, 2H), 7.37 (t, J = 7.8 Hz, 2H), 7.27 (t, J = 8.4 Hz, 1H), 7.19 (d, J = 7.8 Hz, 2H), 2.34 (s, 3H). (3) 4-Methoxybiphenyl δ 7.57-7.52 (m, 4H), 7.42 (t, J = 7.2 Hz, 2H), 7.30 (t, J = 7.2 Hz, 1H), 6.98 (d, J = 9.0 Hz, 2H), 3.85 (s, 3H). (4) 2-Methylbiphenyl δ 7.43-7.35 (m, 2H), 7.34-7.27 (m, 3H), 7.26-7.18 (m, 4H), 2.27 (s, 3H). (5) 4-Acetylbiphenyl δ 8.04 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.62 (d, J = 8.7 Hz, 2H), 7.55-7.30 (m, 3H), 2.64 (s, 3H). (6) 4-Chlorobiphenyl δ 7.68-7.33 (m 9H). (7) 2-biphenylcarbaldehyde δ 9.98 (s, 1H), 8.03 (d, J = 7.80 Hz, 1H), 7.67-7.61 (m, 1H), 7.52-7.36 (m, 7H). (8) 3-Nitrobiphenyl δ 8.43 (s, 1H), 8.18 (d, J = 8.10 Hz, 1H), 7.90 (d, J = 7.80 Hz, 1H), 7.62-7.56 (m, 3H), 7.51-7.39 (m, 3H). (9) p-Terphenyl δ 7.68-7.55 (m, 8H), 7.48-7.44 (m, 4H), 7.38-7.33 (m, 2H). (10) 4-Aminobiphenyl δ 7.52 (d, J = 7.2 Hz, 2H), 7.48-7.35 (m, 4H), 7.25 (t, J = 7.2 Hz, 1H), 6.71 (d, J = 8.7 Hz, 2H), 3.66 (s, 2H). (11) 4, 4′-Dimethoxybiphenyl δ 7.47 (d, J = 9.0 Hz, 4H), 6.95 (d, J = 9.0 Hz, 4H), 3.83 (s, 6H). (12) 4-Methoxy-4′-methylbiphenyl δ 7.50 (d, J = 8.7 Hz, 2H), 7.45 (d, J = 7.8 Hz, 2H), 7.22 (d, J = 7.8 Hz, 2H), 6.96 (d, J = 8.7 Hz, 2H), 3.83 (s, 3H), 2.38 (s, 3H). (13) 4-Methylbiphenyl-2′-carbaldehyde δ 9.98 (s, 1H), 8.00 (d, J = 7.8 Hz, 1H), 7.60 (t, J = 7.5 Hz, 1H), 7.44(s, J = 7.8 Hz, 1H), 7.41 (d, J = 7.5 Hz, 1H), 7.25 (s, 4H), 2.41 (s, 3H). (14) 4-Chloro-4′-methoxybiphenyl δ 7.51-7.46 (m, 4H), 7.39 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.7 Hz, 2H), 3.86 (s, 3H). (15) 4-Nitro-4-methylbiphenyl δ 8.25 (d, J = 8.7 Hz, 2H), 7.72 (d, J = 8.7 Hz, 2H), 7.53 (d, J = 8.1 Hz, 2H), 7.30 (d, J = 8.1 Hz, 2H), 2.42 (s, 3H). (16) 2-Aminobiphenyl δ 7.42-7.38 (m, 4H), 7.36-7.28 (m, 1H), 7.12 (t, J = 7.8 Hz, 2H), 6.80 (t, J = 7.8 Hz, 1H), 6.72 (d, J = 7.8 Hz, 1H), 3.58 (s, 2H). (17) 2-Nitro-4'-methylbiphenyl δ 8.43 (s, 1H), 8.16 (d, J = 8.4 Hz, 1H), 7.89 (d, J = 7.8 Hz, 1H), 7.58 (t, J = 7.8 Hz, 1H), 7.52 (d, J = 8.4 Hz, 2H), 7.30 (d, J = 7.8 Hz, 2H), 2.42 (s, 3H). (18) 4-Methyl-4′-methylbiphenyl δ 7.45 (d, J = 7.8 Hz, 4H), 7.20 (d, J = 7.8 Hz, 4H). (19) 4-Chloro-4′-methylbiphenyl δ 7.50-7.42 (m, 4H), 7.37 (d, J = 8.4 Hz, 2H), 7.24 (d, J = 8.4 Hz, 2H). (20) 1-phenylnaphthalene δ 7.81-7.71 (m, 3H), 7.41-7.29 (m, 9H).