Facile oxidative addition of the phosphorous-selenium bond to Pd(0) and Pt(0) complexes and development of Pd-catalyzed regio- and stereoselective selenophosphorylation of alkynes

Journal of the American Chemical Society

Volumn 118, Issue 29, 1996, Pages 7000-7001

  Han, Li Biao ^a   Choi, Nami ^a   Tanaka, Masato ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; PHOSPHORUS; SELENIUM;

ARTICLE; COMPLEX FORMATION; MOLECULAR INTERACTION; OXIDATION; PHOSPHORYLATION; STEREOCHEMISTRY;

EID: 0029906394     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9608860     Document Type: Article

References (27)

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2. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J. Organometallics 1991, 10, 16. (d) Finckh, W.; Tang, B.-Z.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904.
3. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J. Organometallics 1991, 10, 16. (d) Finckh, W.; Tang, B.-Z.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904.
4. For recent reviews, see: (a) Horn, K. A. Chem. Rev. 1995, 95, 1317. (b) Sharma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. See also: (c) Tanaka, M.; Uchimaru, Y.; Lautenschlager, H.-J. Organometallics 1991, 10, 16. (d) Finckh, W.; Tang, B.-Z.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904.
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10. Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
11. We have recently reported the activation of P-H bonds by transition metal complexes: Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
12. 2 and could become pale yellow.
13. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
14. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
15. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
16. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
17. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
18. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
19. Only very limited studies have been documented on these compounds. For preparations of (alkylseleno)phosphates, see: (a) Melnik, Y. G. Ukr. Khim. Zh. (Russ. Ed.) 1993, 59, 654. (b) Dybowski, P.; Krawczyk, E.; Skowronska, A. Synthesis 1992, 601. (c) Markowka, A.; Buchowiecki, W. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1973, 21, 455. (d) Kataev, E. G.; Mannafov, T. G.; Kostina, G. I. Zh. Obshch. Khim. 1968, 38, 363. For their reactivities, halogenlysis: (e) Krawiecka, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 62, 199. (f) Markowska, A. Bull Acad. Pol. Sci., Ser. Sci. Chim. 1967, 15, 153. Alcolysis: (g) Wozniak, L. A.; Krzyzanowska, B.; Stec, W. J. J. Org. Chem. 1992, 57, 6057.
20. Reviews on the synthetic utility of vinylselenides and vinylphosphonates: (a) Comasseto, J. V. J. Organomet. Chem. 1983, 253, 131. (b) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
21. Reviews on the synthetic utility of vinylselenides and vinylphosphonates: (a) Comasseto, J. V. J. Organomet. Chem. 1983, 253, 131. (b) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
22. P(O)-P1 = 2477.0 Hz).
23. 31P NMR signals centered at 56, 30, and -5 ppm. Unfortunately, however, we have not succeeded in the isolation of the resulting complexes; see the supporting information for more details.
24. 2 was employed.
25. 4, only 15% of the corresponding adduct was obtained. Most of the starting materials remained unreacted.
26. Internal alkynes were unreactive under the present conditions.
27. 6, at 100 °C.