Facile synthesis of aryl(difluoromethyl)phosphonates through CuBr-mediated cross coupling reactions of [(diethoxyphosphinyl)difluoromethyl]zinc bromide with aryl iodides

Tetrahedron

Volumn 53, Issue 3, 1997, Pages 815-822

  Yokomatsu, Tsutomu ^a   Murano, Tetsuo ^a   Suemune, Kenji ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIFLUORO 1 (2 NAPHTHYL)METHYLPHOSPHONIC ACID; PHOSPHONIC ACID DERIVATIVE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031030669     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01063-0     Document Type: Article

References (26)

1. (a) Blackburn, G. M. Chem. Ind. 1981, 134.
2. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc. Perkin Trans. I 1984, 1119.
3. (a) Thatcher, G. R. J.; Campbell, A. S. J. Org.. Chem. 1993, 58, 2272.
4. (b) Nieschalk, J.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1995, 719.
5. (c) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165.
6. For the synthesis of (α,α-difluoromethylene)phosphonatic analogues of natural phosphates with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169.
7. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763.
8. (c)Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227.
9. (d)Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193.
10. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821.
11. (f) Matulic-Adamic, J.; Hacberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563.
12. For the synthesis of protecting variants of 2: (a) Smyth, M. S.; Ford, H., Jr.; Burke, T. R., Jr. Tetrahedron Lett. 1992, 33, 4137.
13. (b) Burke, T. R., Jr.; Smyth, M. S.; Nomizu, M.; Otaka, A.; Roller, P. P. J. Org. Chem. 1993, 58, 1336.
14. (c)Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551.
15. (d)Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537 and references cited therein.
16. Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Biochem. Biophys. Res. Commun. 1994, 204, 129.
17. (a) Smyth, M. S.; Ford, H., Jr.; Burke, T. R., Jr. Tetrahedron Lett. 1992, 33, 4137.
18. (b) Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963.
19. (c) Kole, H. K.; Smyth, M. S.; Russ, P. L.; Burke, T. R., Jr. Biochemical J. 1995, 311, 1025.
20. (a) Percy has recently reported a DAST-free route to aryl(difluoromethyl)phosphonates: Blades, K.; Cockerill, G. S.; Easterfield, H. J.; Lequeux, T. P; Percy, J. M. J. Chem. Soc., Chem. Commun. 1996, 1615.
21. (b) We have experienced that the DAST-mediated difluorination of 4-methyl-α-oxobenzylphosphonate on multi-gram scales reacted explosively.
22. Qiu, W.; Burton, D. J. Tetrahedron Lett. 1996, 37, 2745.
23. For a review of metalated difluoromethylphosphonates: Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189.
24. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207.
25. For effects of ultrasound on organometalic reagents: Petrier, C.; Luche, J.-L.; Dupuy, C. Tetrahedron Lett. 1984, 25, 3463.
26. Prepared from 2-aminonaphthalene according to the method of Schmidlin: Schmidlin, J.; Hub, M. Chem. Ber. 1910, 43, 2824.