The use of potassium alkynyltrifluoroborates in Mannich reactions

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 729-731

  Kabalka, George W ^a   Venkataiah, Bollu ^a   Dong, Gang ^a  

^a NONE

Author keywords

Butylmethylimidazolium tetrafluoroborate; Ionic liquids; Mannich reaction; Potassium alkynyltrifluoroborates; Propargylamines

Indexed keywords

ALKYNYL GROUP; AMINE; BENZOIC ACID; BORONIC ACID DERIVATIVE; BUTYLMETHYLIMIDAZOLIUM TETRAFLUOROBORATE; ORGANOBORON DERIVATIVE; POTASSIUM ALKYNYLTRIFLUOROBORATE; POTASSIUM DERIVATIVE; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; MANNICH REACTION;

EID: 0346787854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.049     Document Type: Article

References (42)

1. Petasis N.A., Akritopoulou I. Tetrahedron Lett. 34:1993;583.
2. (a) Petasis N.A., Zavialov I.A. J. Am. Chem. Soc. 119:1997;445
3. (b) Petasis N.A., Goodman A., Zavialov I.A. Tetrahedron. 53:1997;16463
4. (c) Thompson K.A., Hall D.G. Chem. Commun. 2000;2379
5. (d) Koolmeister T., Sodergren M., Scobie M. Tetrahedron Lett. 43:2002;5965
6. (e) Portlock D.E., Naskar D., West L., Li M. Tetrahedron Lett. 43:2002;6845
7. (f) Naskar D., Roy A., Seibel W.L., Portlock D.E. Tetrahedron Lett. 44:2003;5819.
8. The Petasis reaction has been applied to the synthesis of heterocyclic systems: Hansen T.K., Schlienger N., Hansen B.S., Andersen P.H., Bryce M.R. Tetrahedron Lett. 40:1999;3651 Batey R.A., MacKay D.B., Santhakumar V. J. Am. Chem. Soc. 121:2000;5075 Petasis N.A., Patel Z.D. Tetrahedron Lett. 41: 2000;9607 Berree F., Debache A., Marsac Y., Carboni B. Tetrahedron Lett. 42:2001;3591.
9. The Petasis reaction has been applied to the synthesis of heterocyclic systems: Hansen T.K., Schlienger N., Hansen B.S., Andersen P.H., Bryce M.R. Tetrahedron Lett. 40:1999;3651 Batey R.A., MacKay D.B., Santhakumar V. J. Am. Chem. Soc. 121:2000;5075 Petasis N.A., Patel Z.D. Tetrahedron Lett. 41: 2000;9607 Berree F., Debache A., Marsac Y., Carboni B. Tetrahedron Lett. 42:2001;3591.
10. The Petasis reaction has been applied to the synthesis of heterocyclic systems: Hansen T.K., Schlienger N., Hansen B.S., Andersen P.H., Bryce M.R. Tetrahedron Lett. 40:1999;3651 Batey R.A., MacKay D.B., Santhakumar V. J. Am. Chem. Soc. 121:2000;5075 Petasis N.A., Patel Z.D. Tetrahedron Lett. 41: 2000;9607 Berree F., Debache A., Marsac Y., Carboni B. Tetrahedron Lett. 42:2001;3591.
11. The Petasis reaction has been applied to the synthesis of heterocyclic systems: Hansen T.K., Schlienger N., Hansen B.S., Andersen P.H., Bryce M.R. Tetrahedron Lett. 40:1999;3651 Batey R.A., MacKay D.B., Santhakumar V. J. Am. Chem. Soc. 121:2000;5075 Petasis N.A., Patel Z.D. Tetrahedron Lett. 41: 2000;9607 Berree F., Debache A., Marsac Y., Carboni B. Tetrahedron Lett. 42:2001;3591.
12. (a) Petasis N.A., Zavialov I.A. J. Am. Chem. Soc. 120:1998;11798
13. (b) Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., Olah G.A. Org. Lett. 2:2000;3173
14. (c) Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., Olah G.A. J. Org. Chem. 67:2002;3718.
15. Wang Q., Finn M.G. Org. Lett. 2:2000;4063 Petasis N.A., Boral S. Tetrahedron Lett. 42:2001;539.
16. Wang Q., Finn M.G. Org. Lett. 2:2000;4063 Petasis N.A., Boral S. Tetrahedron Lett. 42:2001;539.
17. Schlienger N., Bryce M.R., Hansen T.K. Tetrahedron Lett. 41:2000;1303.
18. (a) Soulie J., Cadiot P. Bull. Soc. Chim. Fr. 1966;3846
19. (b) Molander G.A., Brown H.C. Synthesis. 1979;104
20. (c) Blanchard C., Framery E., Vaultier M. Synthesis. 1996;45.
21. Soderquist J.A., Matos K., Rune A., Ramos J. Tetrahedron Lett. 36:1995;2401 Furstner A., Seidel G. Tetrahedron. 51:1995;11165 Castanet A.-S., Colobert F., Schlama T. Org. Lett. 2:2000;3559 Oh C.H., Jung S.H. Tetrahedron Lett. 41:2000;8513.
22. Soderquist J.A., Matos K., Rune A., Ramos J. Tetrahedron Lett. 36:1995;2401 Furstner A., Seidel G. Tetrahedron. 51:1995;11165 Castanet A.-S., Colobert F., Schlama T. Org. Lett. 2:2000;3559 Oh C.H., Jung S.H. Tetrahedron Lett. 41:2000;8513.
23. Soderquist J.A., Matos K., Rune A., Ramos J. Tetrahedron Lett. 36:1995;2401 Furstner A., Seidel G. Tetrahedron. 51:1995;11165 Castanet A.-S., Colobert F., Schlama T. Org. Lett. 2:2000;3559 Oh C.H., Jung S.H. Tetrahedron Lett. 41:2000;8513.
24. Soderquist J.A., Matos K., Rune A., Ramos J. Tetrahedron Lett. 36:1995;2401 Furstner A., Seidel G. Tetrahedron. 51:1995;11165 Castanet A.-S., Colobert F., Schlama T. Org. Lett. 2:2000;3559 Oh C.H., Jung S.H. Tetrahedron Lett. 41:2000;8513.
25. (a) Molander G.A., Katona B.W., Machrouhi F. J. Org. Chem. 67:2002;8416
26. (b) Darses S., Michaud G., Genet J.-P. Eur. J. Org. Chem. 1999;1875.
27. Vedejs E., Chapman R.W., Fields S.C., Lin S., Schrimpf M.R. J. Org. Chem. 60:1995;3020 Darses S., Michaud G., Genet J.-P. Tetrahedron Lett. 39:1998;5045 Molander G.A., Rivero M.R. Org. Lett. 4:2002;107 Molander G.A., Biolatto B. Org. Lett. 4:2002;1867.
28. Vedejs E., Chapman R.W., Fields S.C., Lin S., Schrimpf M.R. J. Org. Chem. 60:1995;3020 Darses S., Michaud G., Genet J.-P. Tetrahedron Lett. 39:1998;5045 Molander G.A., Rivero M.R. Org. Lett. 4:2002;107 Molander G.A., Biolatto B. Org. Lett. 4:2002;1867.
29. Vedejs E., Chapman R.W., Fields S.C., Lin S., Schrimpf M.R. J. Org. Chem. 60:1995;3020 Darses S., Michaud G., Genet J.-P. Tetrahedron Lett. 39:1998;5045 Molander G.A., Rivero M.R. Org. Lett. 4:2002;107 Molander G.A., Biolatto B. Org. Lett. 4:2002;1867.
30. Vedejs E., Chapman R.W., Fields S.C., Lin S., Schrimpf M.R. J. Org. Chem. 60:1995;3020 Darses S., Michaud G., Genet J.-P. Tetrahedron Lett. 39:1998;5045 Molander G.A., Rivero M.R. Org. Lett. 4:2002;107 Molander G.A., Biolatto B. Org. Lett. 4:2002;1867.
31. (a) Welton T. Chem. Rev. 99:1999;2071
32. (b) Wasserscheid P., Kein W. Angew. Chem., Int. Ed. 39:2000;3772
33. (c) Sheldon R. Chem. Commun. 2001;2399
34. (d) Dupont J., de Souza R.F., Surez P.A.Z. Chem. Rev. 102:2002;3667.
35. Kabalka G.W., Malladi R.R. Chem. Commun. 2000;2191 Kabalka G.W., Dong G., Venkataiah B. Org. Lett. 5:2003;893 Kabalka G.W., Venkataiah B., Dong G. Tetrahedron Lett. 44:2003;4673 Kabalka, G. W.; Venkataiah, B.; Das, B. C. Synlett, in press.
36. Kabalka G.W., Malladi R.R. Chem. Commun. 2000;2191 Kabalka G.W., Dong G., Venkataiah B. Org. Lett. 5:2003;893 Kabalka G.W., Venkataiah B., Dong G. Tetrahedron Lett. 44:2003;4673 Kabalka, G. W.; Venkataiah, B.; Das, B. C. Synlett, in press.
37. Kabalka G.W., Malladi R.R. Chem. Commun. 2000;2191 Kabalka G.W., Dong G., Venkataiah B. Org. Lett. 5:2003;893 Kabalka G.W., Venkataiah B., Dong G. Tetrahedron Lett. 44:2003;4673 Kabalka, G. W.; Venkataiah, B.; Das, B. C. Synlett, in press.
38. Musso D.L., Clarke M.J., Kelly J.L., Boswell G.E., Chen G. Org. Biomol. Chem. 1:2003;498.
39. Jun C.-H., Lee D.-Y., Hong J.-B. Angew. Chem., Int. Ed. 39:2000;3070.
40. 4 (800 mg), potassium 1-hexynyltrifluoroborate (1 mmol) and benzoic acid (1 mmol) were added. The mixture was stirred at 80 °C for 20 h, the product was extracted into diethyl ether (3 × 5 mL), the solvent removed, and the crude product purified by column chromatography (silica gel).
41. (a) Luo F.-T., Schreuder I., Wang R.-T. J. Org. Chem. 57:1992;2213
42. (b) Larock R.C., Yue D. Tetrahedron Lett. 42:2001;6011. and references cited therein.