Sodium 2-(2-pyridin-3-ylethylamino)sulfonate: an efficient ligand and base for palladium-catalyzed Heck reaction in aqueous media

Tetrahedron Letters

Volumn 49, Issue 27, 2008, Pages 4252-4255

  Pawar, Shivaji S ^a   Dekhane, Deepak V ^a   Shingare, Murlidhar S ^b   Thore, Shivaji N ^a  

^a Vinyakrao Patil Mahavidyala Vaijapur ^*  (India)

^b DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Alkene; Aqueous media; Aryl halide; Heck coupling; N Donor ligand; Palladium catalyzed

Indexed keywords

ALKENE DERIVATIVE; HALIDE; LIGAND; PALLADIUM; SODIUM 2 (2 PYRIDIN 3 YLETHYLAMINO)SULFONATE; SULFONIC ACID DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; HECK REACTION;

EID: 44249110675     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.148     Document Type: Article

References (45)

1. Mizoroki T., Mori K., and Ozaki A. Bull. Chem. Soc. Jpn. 44 (1971) 581
2. Heck R.F., and Nolley Jr. J.P. J. Org. Chem. 37 (1972) 2320
3. For selected reviews on the Heck reaction, see:. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
4. Dounay A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945
5. Whitcombe N.J., Hii K.K., and Gibson S.E. Tetrahedron 57 (2001) 7449
6. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
7. Shibasaki M., and Vogl E.M. J. Organomet. Chem. 576 (1999) 1
8. Crisp G.T. Chem. Soc. Rev. 27 (1998) 427
9. Shibasaki M., Boden C.D.J., and Kojima A. Tetrahedron 53 (1997) 7371
10. Negishi E., Cope'ret C., Ma S., Liou S.-Y., and Liu F. Chem. Rev. 96 (1996) 365
11. De Meijere A., and Meyer F.E. Angew. Chem., Int. Ed. Engl. 33 (1995) 2379
12. Cabri W., and Candiani I. Acc. Chem. Res. 28 (1995) 2
13. For a general introduction to organic reactions in water, see:. Li C.J. Chem. Rev. 105 (2005) 3095
14. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie Academic and Professional, London
15. Li C.J., and Chan T.H. Organic Reactions in Aqueous Media (1997), Wiley, New York
16. Li C.J. Chem. Rev. 93 (1993) 2023
17. Genet J.-P., and Savignac M. J. Organomet. Chem. 576 (1999) 305
18. Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., and Sharpless K.B. Angew. Chem., Int. Ed. 44 (2005) 3275
19. Lindstrom U.M. Chem. Rev. 102 (2002) 2751
20. Wei C., and Li C.-J. J. Am. Chem. Soc. 125 (2003) 9584
21. For recent examples, see:. Arvela R.K., and Leadbeater N.E. J. Org. Chem. 70 (2005) 1786
22. Hagiwara H., Sugawara Y., Hoshi T., and Suzuki T. Chem. Commun. (2005) 2942
23. Bhattacharya S., Srivastavaa A., and Sengupta S. Tetrahedron Lett. 46 (2005) 3557
24. Botella L., and Najera C. Tetrahedron Lett. 45 (2004) 1833
25. Solabannavar S.B., Desai U.V., and Mane R.B. Green Chem. 4 (2002) 347
26. Mukhopadhyay S., Rothenberg G., Joshi A., Baidossi M., and Sasson Y. Adv. Synth. Catal. 344 (2002) 348
27. Ansos M.S., Mirza A.R., Tonks L., and William J.M.J. Tetrahedron Lett. 40 (1999) 7147
28. Uozumi Y., and Kimura T. Synlett (2002) 2045
29. Botella L., and Najera C. J. Org. Chem. 70 (2005) 4360
30. Najera C., Gil-molto J., Karlstrom S., and Falvello L.R. Org. Lett. 5 (2003) 1451
31. Jeffery T. Tetrahedron 52 (1996) 10113
32. Heck couplings proceeding in organic solvents at room temperature in the presence of air-sensitive phosphine ligands or catalyzed by chloro-palladated propargylamine have been reported, see:. Littke A.F., and Fu G.C. J. Am. Chem. Soc. 123 (2001) 6989
33. Stambuli J.P., Stauffer S.R., Shaughnessy K.H., and Hartwig J.F. J. Am. Chem. Soc. 123 (2001) 2677
34. Consorti C.S., Zanini M.L., Leal S., Ebeling G., and Dupont J. Org. Lett. 5 (2003) 983
35. For selected recent reviews of the Heck reaction see:. Brase S., and de Meijere A. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim, Germany Chapter 3
36. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
37. Whitcombe N.J., Hii K.K., and Gibson S.E. Tetrahedron 57 (2001) 7449
38. Battace A., Feuerstein M., Lemhadri M., Zair T., Doucet H., and Santelli M. Eur. J. Org. Chem. 7 (2007) 3122
39. Ackermann L., Kaspar L., and Gschrei C. Chem. Commun. (2004) 2824
40. Mini T., Shirae Y., Sasai Y., Sakamoto M., and Fujita T. J. Org. Chem. 71 (2006) 6834
41. Li H.J., and Wang L. Eur. J. Org. Chem. 22 (2006) 5099
42. Pawar S.S., Shingare M.S., and Thore S.N. Lett. Org. Chem. 4 (2007) 486
43. Liand H.C., Das S.K., Galvan J.R., Satio S.M., and Zhang Y. Green Chem. 7 (2005) 410
44. Zhang Z., Zha Z., Gan C., Pan C., Zhou Y., Wang Z., and Zhou M.-M. J. Org. Chem. 71 (2006) 4339
45. Zhou L., and Wang L. Synthesis 16 (2006) 2653