High reactivity of a five-membered cyclic hydrogen phosphonate leading to development of facile palladium-catalyzed hydrophosphorylation of alkenes [11]

Journal of the American Chemical Society

Volumn 122, Issue 22, 2000, Pages 5407-5408

  Han, Li Biao ^a   Mirzaei, Farzad ^a   Zhao, Chang Qiu ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HALIDE; HYDROGEN; PALLADIUM; PHOSPHONIC ACID DERIVATIVE;

CATALYSIS; CATALYST; GAS CHROMATOGRAPHY; HYDROLYSIS; ISOMER; LETTER; PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034616854     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000444v     Document Type: Letter

References (29)

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3. Recent reviews: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. (c) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. (d) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957. (e) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
4. Recent reviews: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. (c) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. (d) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957. (e) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
5. Recent reviews: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. (c) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179. (d) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957. (e) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
6. (a) Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; Wiley-Interscience: New York, 1972.
7. (b) Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992.
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9. 2 to alkenes are well-known (ref 2). For recent examples, see: (a) Nifant'ev, E. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Vasyanina, L. K. Russ. J. Gen. Chem. 1993, 63, 1201.
10. (b) Nifant'ev, E. E.; Magdeeva, R. K.; Dolidze, A. V.; Ingorokva, K. V.; Samkharadze, L. O.; Vasyanina, L. K.; Bekker, A. R. Zh. Obshch. Khim. 1991, 61, 96.
11. (c) Nifant'ev, E. E.; Magdeeva, R. K.; Shchepet'eva, N. P. Zh. Obshch. Khim. 1980, 50, 1744.
12. Metal-catalyzed addition to alkenes usually is more difficult to achieve than the corresponding addition to alkynes. (a) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336. (b) Iverson, C. N.; Smith, M. R., III Organometallics 1997, 16, 2757. (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689. (d) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516. (e) Kondo, T.; Uenoyama, S.-y.; Fujita, K.-i.; Mitsudo, T.-a. J. Am. Chem. Soc. 1999, 121, 482.
13. Metal-catalyzed addition to alkenes usually is more difficult to achieve than the corresponding addition to alkynes. (a) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336. (b) Iverson, C. N.; Smith, M. R., III Organometallics 1997, 16, 2757. (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689. (d) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516. (e) Kondo, T.; Uenoyama, S.-y.; Fujita, K.-i.; Mitsudo, T.-a. J. Am. Chem. Soc. 1999, 121, 482.
14. Metal-catalyzed addition to alkenes usually is more difficult to achieve than the corresponding addition to alkynes. (a) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336. (b) Iverson, C. N.; Smith, M. R., III Organometallics 1997, 16, 2757. (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689. (d) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516. (e) Kondo, T.; Uenoyama, S.-y.; Fujita, K.-i.; Mitsudo, T.-a. J. Am. Chem. Soc. 1999, 121, 482.
15. Metal-catalyzed addition to alkenes usually is more difficult to achieve than the corresponding addition to alkynes. (a) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336. (b) Iverson, C. N.; Smith, M. R., III Organometallics 1997, 16, 2757. (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689. (d) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516. (e) Kondo, T.; Uenoyama, S.-y.; Fujita, K.-i.; Mitsudo, T.-a. J. Am. Chem. Soc. 1999, 121, 482.
16. Metal-catalyzed addition to alkenes usually is more difficult to achieve than the corresponding addition to alkynes. (a) Baker, R. T.; Nguyen, P.; Marder, T. B.; Westcott, S. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1336. (b) Iverson, C. N.; Smith, M. R., III Organometallics 1997, 16, 2757. (c) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689. (d) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2516. (e) Kondo, T.; Uenoyama, S.-y.; Fujita, K.-i.; Mitsudo, T.-a. J. Am. Chem. Soc. 1999, 121, 482.
17. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
18. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring- strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
19. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring-strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
20. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring- strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
21. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring- strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
22. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring- strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
23. 3 and pinacol. (a) Zwierrzak, A. Can. J. Chem. 1967, 45, 2501. (b) Munoz, A.; Hubert, C.; Luche, J.-L. J. Org. Chem. 1996, 61, 6015. Very little is known about its reactivity. The O-P-O angle in the ring was estimated at ca. 99°, 5° smaller than the normal angle for the acyclic analogues, resulting in a ring- strain energy of ca. 5-6 kcal/mol, which makes 1a more acidic. (c) Ovchinnikov, V. V.; Galkin, V. I.; Yarkova, E. G.; Markova, L. E.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1978, 48, 2424. (d) Newton, M. G.; Campbell, B. S. J. Am. Chem. Soc. 1974, 96, 7790. (e) Ovchinnikov, V. V.; Lapteva, L. I.; Sagadeev, E. V.; Konovalov, A. I. Thermochim. Acta 1996, 288, 105. (f) Ovhinnikov, V. V.; Cherezov, S. V.; Cherkasov, R. A.; Pudovik, A. N. Zh. Obshch. Khim. 1985, 55, 1244.
24. 3P(O) is well-established. (a) Hudson, R. F.; Brown, C. Acc. Chem. Res. 1972, 5, 204. (b) Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
25. 3P(O) is well-established. (a) Hudson, R. F.; Brown, C. Acc. Chem. Res. 1972, 5, 204. (b) Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
26. 33% of 1a remained unchanged. 2-Octenes (31%, cis/trans = 36/64), which was inert toward the hydrophosphorylation under present conditions, was also formed.
27. 2 (Pd/P = 1/2) as the catalyst (82% isolated yield of 2a).
28. 3 to acrylonitrile. (a) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. (b) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701.
29. 3 to acrylonitrile. (a) Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. (b) Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701.