Irregularities in the effect of potassium phosphate in ynamide synthesis

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9447-9450

  Dooleweerdt, Karin ^a,b   Birkedal, Henrik ^a   Ruhland, Thomas ^b   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; HYDRATES; ORGANIC COMPOUNDS; POTASSIUM;

CHEMICAL EQUATIONS; HIGH QUALITIES; POTASSIUM PHOSPHATES; REGIOSELECTIVE HYDROAMINATION; SECOND GENERATIONS;

SYNTHESIS (CHEMICAL);

AMIDE; CARBAMIC ACID DERIVATIVE; POTASSIUM DIHYDROGEN PHOSPHATE; UNCLASSIFIED DRUG; YNAMIDE; ALKYNE; COPPER; PHOSPHATE; POTASSIUM; POTASSIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; REGIOSELECTIVITY; SYNTHESIS; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; ORGANIC CHEMISTRY; PROCEDURES; THERMOGRAVIMETRY; TIME;

ALKYNES; AMIDES; CARBAMATES; CATALYSIS; CHEMISTRY, ORGANIC; COPPER; MODELS, CHEMICAL; PHOSPHATES; POTASSIUM; POTASSIUM COMPOUNDS; SPECTROPHOTOMETRY, INFRARED; THERMOGRAVIMETRY; TIME FACTORS;

EID: 57449118696     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801935b     Document Type: Article

References (46)

1. (a) Li, H.; You, L.; Zhang, X.; Johnson, W. L.; Figueroa, R.; Hsung, R. P. Heterocycles 2007, 74, 553.
2. (b) Tanaka, K.; Takeishi, K. Synlett 2007, 2920.
3. (c) Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815.
4. (d) Tracey, M. R.; Oppenheimer, J.; Hsung, R. P. J. Org. Chem. 2006, 71, 8629.
5. (e) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
6. (f) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Synth. Cat. 2006, 348, 2437.
7. (g) Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 8, 2679.
8. (h) Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 14, 2679.
9. (i) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
10. (a) Zhang, X.; Hsung, R. P.; Li, H. Chem. Commun. 2007, 23, 2420.
11. (b) Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2006, 8, 231.
12. (a) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
13. (b) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925.
14. (c) Hashmi, S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem. - Eur. J. 2008, 14, 6672.
15. (d) Couty, S.; Meyer, C.; Cossy, J. Angew. Chem., Int. Ed. 2006, 45, 6726.
16. (e) Chechik-Lankin, H.; Livshin, S.; Marek, I. Synlett 2005, 2098.
17. (f) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209.
18. (g) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
19. (h) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
20. Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047.
21. (a) Kurtz, K. C. M.; Frederick, M. O.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P. Tetrahedron 2006, 62, 3928.
22. (b) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663.
23. Couty, S.; Meyer, C.; Cossy, J. Synlett 2007, 2819.
24. Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett. 2008, 10, 3477.
25. Al-Rashid, Z. F.; Hsung, R. P. Org. Lett. 2008, 10, 661.
26. Song, Z.; Lu, T.; Hsung, R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 4069.
27. Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361.
28. For a special issue dedicated to the chemistry of ynamides, see: Tetrahedron-Symposium-In-Print: "Chemistry of Electron-Deficient Ynamines and Ynamides." Tetrahedron 2006, 62, Issue no. 16.
29. (a) Sagamanova, I. K.; Kurtz, K. C. M.; Hsung, R. P. Org. Synth. 2007, 84, 359.
30. (b) Zhang, X.; Zhang, Y.; Huang, J; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170.
31. (c) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151.
32. For another protocol for copper catalyzed ynamide synthesis, see: (a) Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815.
33. (b) Kohnen, A. L.; Dunetz, J. R.; Danheiser, R. L. Org. Synth. 2007, 84, 88.
34. (a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
35. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
36. (c) Klapars, A.; Antilla, J.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
37. 4 was obtained from the following sources: (A) from Sigma Aldrich (P5629), (B) from Riedel-de Haën through Sigma Aldrich/Fluka (04347), (C) from Acros Organics (38768), (D) from Strem Chemicals (19-3800), and (E) from Alfa Aesar (041587).
38. For further information on the powder X-ray diffraction analysis, see the Supporting Information.
39. Fits were done to a sum of Lorentzians including a background term and possibly an auxiliary peak for leveling background to left/right of peak cluster and/or describing details of neighboring peaks. See Supporting Information for further details on the analysis by infrared spectroscopy.
40. For further information on the results achieved by T.G.A., see the Supporting Information.
41. 4 would be present.
42. 4. Drying has been attempted at 150°C for several hours with no success.
43. (a) Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
44. (b) Siemsen, P; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
45. 4 obtained from Riedel de-Haën (B).
46. 4 obtained Acros Organics (C).