Development of a room temperature Hirao reaction

Tetrahedron Letters

Volumn 50, Issue 4, 2009, Pages 457-459

  Kohler, Mark C ^a   Sokol, Joseph G ^a   Stockland Jr , Robert A ^a  

^a BUCKNELL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLADIUM; IODINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; ROOM TEMPERATURE; SUBSTITUTION REACTION; TEMPERATURE MEASUREMENT;

EID: 57149135044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.040     Document Type: Article

References (34)

1. Dolman N.P., More J.C.A., Alt A., Knauss J.L., Troop H.M., Bleakman D., Collingridge G.L., and Jane D.E. J. Med. Chem. 49 (2006) 2579
2. Kim Y.C., Brown S.G., Harden T.K., Boyer J.L., Dubyak G., King B.F., Burnstock G., and Jacobson K.A. J. Med. Chem. 44 (2001) 340
3. Bigge C.F., Johnson G., Ortwine D.F., Drummond J.T., Retz D.M., Brahce L.J., Coughenour L.L., Marcoux F.W., and Probert A.W. J. Med. Chem. 35 (1992) 1371
4. Scapin G., Patel S.B., Becker J.W., Wang Q., Desponts C., Waddleton D., Skorey K., Cromlish W., Bayly C., Therien M., Gauthier J.Y., Li C.S., Lau C.K., Ramachandran C., Kennedy B.P., and Asante-Appiah E. Biochemistry 42 (2003) 11451
5. Nagarajan R., and Pratt R.F. Biochemistry 43 (2004) 9664
6. Petrakis K.S., and Nagabhushan T.L. J. Am. Chem. Soc. 109 (1987) 2831
7. Sawa M., Kiyoi T., Kurokawa K., Kumihara H., Yamamoto M., Miyasaka T., Ito Y., Hirayama R., Inoue T., Kirii Y., Nishiwaki E., Ohmoto H., Maeda Y., Ishibushi E., Inoue Y., Yoshino K., and Kondo H. J. Med. Chem. 45 (2002) 919
8. Ma D., Tian H., and Zou G. J. Org. Chem. 64 (1999) 120
9. Vedejs E., Daugulis O., Diver S.T., and Powell D.R. J. Org. Chem. 63 (1998) 2338
10. Prim D., Campagne J., Joseph D., and Andrioletti B. Tetrahedron 58 (2002) 2041
11. Inoue A., Shinokubo H., and Oshima K. J. Am. Chem. Soc. 125 (2003) 1484
12. Onouchi H., Miyagawa T., Furuko A., Maeda K., and Yashima E. J. Am. Chem. Soc. 127 (2005) 2960
13. Onouchi H., Maeda K., and Yashima E. J. Am. Chem. Soc. 123 (2001) 7441
14. Allcock H.R., Hofmann M.A., Ambler C.M., and Morford R.V. Macromolecules 35 (2002) 3484
15. Hirao T., Masunaga T., Yamada N., Ohshiro Y., and Agawa T. Bull. Chem. Soc. Jpn. 55 (1982) 909
16. Hirao T., Masunaga T., Ohshiro Y., and Agawa T. Synthesis (1981) 56
17. Schwan A.L. Chem. Soc. Rev. 33 (2004) 218
18. Huang C., Tang X., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 71 (2006) 5020
19. Yao Q., and Levchik S. Tetrahedron Lett. 47 (2006) 277
20. Goossen L.J., and Dezfuli M.K. Synlett (2005) 445
21. Bravo-Altamirano K., Huang Z., and Montchamp J. Tetrahedron 61 (2005) 6315
22. Rao H.H., Jin Y., Fu H., Jiang Y.Y., and Zhao Y.F. Chem. Eur. J. 12 (2006) 3636
23. Kalek, M.; Ziadi, A.; Stawinski, J. Org. Lett. 2008 ASAP article (Sept. 23, 2008).
24. Belabassi Y., Alzghari S., and Montchamp J. J. Organomet. Chem. 693 (2008) 3171
25. Stockland Jr. R.A., Lipman A.J., Bawiec III J.A., Morrison P.E., Guzei I.A., Findeis P.M., and Tamblin J.F. J. Organomet. Chem. 691 (2006) 4042
26. Stockland Jr. R.A., Taylor R.I., Thompson L.E., and Patel P.B. Org. Lett. 7 (2005) 851
27. Stone J.J., Stockland Jr. R.A., Reyes J.M., Kovach J., Goodman C.C., and Tillman E.S. J. Mol. Catal. A: Chem. 226 (2005) 11
28. 2bipy = 4,4′-ditertbutyl,2-2′-bipyridine.
29. van Leeuwen P.W.N.M., Kamer P.C.J., Reek J.N.H., and Dierkes P. Chem. Rev. 100 (2000) 2741
30. Kohler M.C., Stockland Jr. R.A., and Rath N.P. Organometallics 25 (2006) 5746
31. Stockland Jr. R.A., Levine A.M., Giovine M.T., Guzei I.A., and Cannistra J.C. Organometallics 23 (2004) 647
32. Levine A.M., Stockland Jr. R.A., Clark R., and Guzei I. Organometallics 21 (2002) 3278
33. 2, THF (3.0 mL) was added. If the aryl halide was a liquid, it was added after the solvent. The reaction was stirred in the dark for 16 h and centrifuged. The solution was decanted and the volatiles were removed under vacuum at 25 °C. The arylphosphonates were isolated using column chromatography (silca gel, pentane/ethyl acetate).
34. The silver salt prepared in this study was stored under nitrogen and in the absence of light (25 °C). Under these conditions, the salt was quite stable for several weeks. Slight decomposition was noted after several months.