Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols. Preparation of cinnamyl-H-phosphinic acid

Organic Syntheses

Volumn 85, Issue , 2008, Pages 96-105

  Bravo Altamirano, Karla ^b   Montchamp, Jean Luc ^a   Rudolph, Alena ^b   Lautens, Mark ^b  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

^b NONE

Author keywords

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Indexed keywords

EID: 85026892946     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.085.0096     Document Type: Article

References (26)

1. Richardson, D.; Sadi, B. B. M.; Caruso, J. A. in Ultra-Trace Analysis of Organophosphorus Chemical Warfare Agent Degradation Products by HPLC-ICP-MS. Agilent Technologies, Online Literature at www.agilent.com/chem.
2. Reviews: (a) Muzart, J. Tetrahedron 2005, 61, 4179-4212.
3. (b) Tamaru, Y. Eur. J. Org. Chem. 2005, 2647-2656.
4. Examples of direct allylation without additives: (a) Olsson, V. J.; Sebelius, S.; Selander, N.; Szabó, K. J. J. Am. Chem. Soc. 2006, 128, 4588-4589.
5. (b) Kayaki, Y.; Koda, T.; Ikariya, T. Eur. J. Org. Chem. 2004, 4989-4993.
6. (c) Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595-2597.
7. (d) Trost, B. M.; Spagnol, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 2083-2096.
8. (e) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535-536.
9. (a) Lu, X.; Zhu, J. Synthesis 1986, 563-564.
10. (b) Lu, X.; Zhu, J.; Huang, J.; Tao, X. J. Mol. Catal. 1987, 41, 235-243.
11. (c) Lu, X.; Tao, X.; Zhu, J.; Sun, X.; Xu, J. Synthesis 1989, 848-850.
12. (d) Lu, X.; Zhu, J. J. Organomet. Chem. 1986, 304, 239.
13. (e) Fiaud, J. C. J. Chem. Soc. Chem. Commun. 1983, 1055-1056.
14. Reviews: (a) Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388-2406.
15. (b) Montchamp, J.-L. Specialty Chemicals Magazine 2006, 26, 44-46.
16. (c) Bravo-Altamirano, K.; Montchamp, J.-L., “Phosphinic Acid, Alkyl Esters” in Encyclopedia of Reagents for Organic Synthesis (eEROS). In press.
17. Bravo-Altamirano, K.; Huang, Z.; Montchamp, J.-L. Tetrahedron 2005, 61, 6315-6329.
18. Bravo-Altamirano, K.; Montchamp, J.-L. Poster 313, 231st National Meeting of the American Chemical Society, Atlanta, March, 2006.
19. Bravo-Altamirano, K.; Montchamp, J.-L. Org. Lett. 2006, 8, 4169-4171.
20. Boyd, E. A.; Regan, A. C.; James, K. Tetrahedron Lett. 1994, 35, 4223-4226.
21. (a) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123.
22. (b) Majewski, P. Phosphorus, Sulfur Silicon 1989, 45, 151-154
23. (c) Kurdyumova, N. R.; Ragulin, V. V.; Tsvetkov, E. N. Russ. J. Gen. Chem. 1994, 64, 380-383.
24. Abrunhosa-Thomas, I.; Ribière, P.; Adcock, A. C.; Montchamp, J.-L. Synthesis 2006, 2, 325-331.
25. (b) Gallagher, M. J.; Ranasinghe, M. G.; Jenkins, I. D. Phosphorus, Sulfur, Silicon 1996, 115, 255-259.
26. Baylis, E. K. Tetrahedron Lett. 1995, 36, 9385-9388.