Three-component coupling of aldehyde, alkyne, and amine catalyzed by silver in ionic liquid

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2443-2446

  Li, Zigang ^a   Wei, Chunmei ^a   Chen, Liang ^a   Varma, Rajender S ^b   Li, Chao Jun ^a,c  

^a Tulane University   (United States)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

Alkyne; Catalysis; Imine; Ionic liquid; Silver

Indexed keywords

ALDEHYDE; ALKYNE; AMINE; COPPER; GOLD; ORGANIC SOLVENT; SILVER;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CYCLIZATION; DIELS ALDER REACTION; GRIGNARD REACTION; REACTION ANALYSIS; SOLVENT EFFECT;

EID: 1242270576     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.044     Document Type: Article

References (44)

1. Anastas P.T., Warner J.C. Green Chemistry: Theory and Practice. 1998;Oxford University, Oxford.
2. Li C.J. Tetrahedron. 52:1996;5643.
3. Chan T.H., Isaac M.B. Pure Appl. Chem. 68:1996;919.
4. Li C.J., Chan T.H. Organic Reactions in Aqueous Media. 1997;John Wiley, New York.
5. Grieco P.A. Organic Synthesis in Water. 1998;Thomson Science, Glasgow.
6. Li C.J. Chem. Rev. 93:1993;2023.
7. Li C.J., Chan T.H. Tetrahedron. 55:1999;11149.
8. Trost B.M. Science. 254:1991;1471.
9. For recent review, see: Naota I., Takaya H., Murahashi S.I. Chem. Rev. 98:1998;2599.
10. Dyker G. Angew. Chem. 38:1999;1698.
11. Li C.J. Acc. Chem. Res. 35:2002;533.
12. Wei C.M., Li C.J. Green Chem. 4:2002;39.
13. Li C.J., Wei C.M. Chem. Commun. 2002;268.
14. Zhang J.H., Wei C.M., Li C.J. Tetrahedron Lett. 43:2002;5731.
15. Wei C.M., Li Z.G., Li C.J. Org. Lett. 5:2003;4473.
16. Carreira E.M. Acc. Chem. Res. 33:2000;373. and references cited therein.
17. see also: Lu G., Li X., Chan W.L., Chan A.S.C. Chem. Commun. 2002;172.
18. Chen Z.L., Xiong W.N., Jiang B. Chem. Commun. 2002;2098.
19. Koradin C., Polborn K., Knochel P. Angew. Chem., Int. Ed. 41:2002;2535.
20. Wei C.M., Li C.J. J. Am. Chem. Soc. 124:2002;5638.
21. Wei C.M., Li C.J. J. Am. Chem. Soc. 125:2003;9584.
22. Wasserscheid P., Keim W. Angew. Chem., Int. Ed. 39:2000;3772.
23. Huddleston J.G., Willauer H.D., Swatloski R.P., Visser A.E., Rogers R.D. Chem. Commun. 1998;1765.
24. Steines S., Drieben-Holscher B., Wasserscheid P. J. Prakt. Chem. 342:2000;348.
25. Song C.E., Roh E.J. Chem. Commun. 2000;837.
26. Chauvin, Y.; Oliver, H.; Mubamann, L. FR 95/14,147, 1995; [Chem. Abstr. 1997, 127, P341298k].
27. Chen W., Xu L., Chatterton C., Xiao J. Chem. Commun. 1999;1247.
28. Yang X.F., Wang M.W., Varma R.S., Li C.J. Org. Lett. 5:2003;657.
29. Keh C.C.K., Namboodiri V.V., Varma R.S., Li C.J. Tetrahedron Lett. 43:2002;4993.
30. Loncaric C., Manabe K., Kobayashi S. Adv. Synth. Catal. 345:2003;475.
31. Patmore N.J., Hague C., Cotgreave J.H., Mahon M.F., Frost C.G., Weller A.S. Chem. Eur. J. 8:2002;2088.
32. Longmire J.M., Wang B., Zhang X. J. Am. Chem. Soc. 124:2002;13400.
33. Hayashi T., Uozumi Y., Yamazaki A., Sawamura M., Hamashima H., Ito Y. Tetrahedron Lett. 32:1991;2799.
34. Yanagisawa A., Matsumoto Y., Asakawa K., Yamamoto H. Tetrahedron. 58:2002;8331.
35. Momiyama N., Yamamoto H. J. Am. Chem. Soc. 125:2003;6038.
36. Jiang, B.; Wang, Q.; Xiong, W.; Zhang, M. Faming Zhuanli Shenqing Gongkai Shuomingshu 2001,CN1314344 A 20010926 CAN 137:369733 AN2002:931697.
37. Koseki Y., Omino K., Anzai S., Nagasaka T. Tetrahedron Lett. 41:2000;2377.
38. Xu C., Negishi E.I. Tetrahedron Lett. 40:1999;431.
39. Wipf P., Methot J.L. Org. Lett. 1:1999;1253.
40. Dalla V., Pale P. New J. Chem. 23:1999;803.
41. Yamasaki S., Fujii K., Wada R., Kanai M., Shibasaki M. J. Am. Chem. Soc. 124:2002;6536.
42. Bates R.W., Satcharoen V. Chem. Soc. Rev. 31:2002;12.
43. Burgess K. Chem. Ind. 18:1999;716.
44. Bianchini C., Glendenning L. Chemtracts. 10:1997;339.