Oxidative heck-type reaction involving cleavage of a carbon-phosphorus bond of arylphosphonic acids

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1484-1485

  Inoue, Atsushi ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXYPHENYLPHOSPHONIC ACID; 4 METHOXYSTILBENE; ACRYLIC ACID DERIVATIVE; CARBON; DIOXANE; FLUORIDE; N,N DIMETHYLFORMAMIDE; ORGANOPHOSPHORUS COMPOUND; PALLADIUM; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STILBENE DERIVATIVE; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; HECK REACTION; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0037433255     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026758v     Document Type: Article

References (30)

1. (a) Sakamoto, M.; Shimizu, I.; Yamamoto, A. Chem. Lett. 1995, 1101.
2. (b) Segelstein, B. E.; Butler, T. W.; Chenard, B. L. J. Org. Chem. 1995, 60, 12.
3. (c) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
4. (d) Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441.
5. For reviews, see: (e) Garrou, P. E. Chem. Rev. 1985, 85, 171.
6. (f) Ortiz, J. V.; Havlas, Z.; Hoffmann, R. Helv. Chim. Acta 1984, 67, 1.
7. Oxidative addition of a C-P bond of acylphosphonates to transition metal complexes, see: Nakazawa, H.; Matsuoka, Y.; Nakagawa, Y.; Miyoshi, K. Organometallics 1992, 11, 1385.
8. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
9. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
10. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
11. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
12. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
13. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
14. 2 to C-C multiple bonds via H-P bond cleavage, see: (a) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. (b) Han, L.-B.; Mirzaei, F.; Zhao, C.-Q.; Tanaka, M. J. Am. Chem. Soc, 2000, 122, 5407. (c) Zhao, C.-Q.; Han, L.-B.; Tanaka, M. Organometallics 2000, 19, 4196. (d) Zhao, C.-Q.; Han, L.-B.; Goto, M.; Tanaka, M. Angew. Chem. 2001, 113, 1983; Angew. Chem., Int. Ed. 2001, 40, 1929. (e) Mirzaei, F.; Han, L.-B.; Tanaka, M. Tetrahedron Lett. 2001, 42, 297. (f) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
15. Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
16. Cho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.
17. (a) Hirabayashi, K.; Ando, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Synlett 1999, 99.
18. (b) Hirabayashi, K.; Ando, J.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1409.
19. (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
20. (b) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774, See also ref 6b.
21. (a) Asano, R.; Moritani, I.; Fujiwara, Y.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2910.
22. (b) Kawamura, T.; Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1977, 50, 2021.
23. Motoba, K.; Motofusa, S.; Cho, C. S.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1999, 574, 3.
24. After submission of our manuscript, the oxidative Heck-type reaction with carboxylic acids has been reported. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
25. The dissociation energy of a P-F bond is 117 kcal/mol.
26. Caution: A combination of phosphorous compounds and fluoride can be highly toxic in the absence of water. The use of anhydrous reaction conditions should be avoided.
27. (a) Holmes, R. R. Pentacoordinated Phosphorus - Structure and Spectroscopy; ACS Monographs 175, 176; American Chemical Society: Washington, DC, 1980; Vols. I, II.
28. (b) Kajiyama, K.; Yoshimune, M.; Nakamoto, M.; Matsukawa, S.; Kojima, S.; Akiba, K.-y. Org. Lett. 2001, 3, 1873.
29. (c) Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Organomet. Chem. 2002, 646, 277.
30. 19F could be observed.