Catalytic hydrophosphination of styrenes

Organic Letters

Volumn 4, Issue 5, 2002, Pages 761-763

  Shulyupin, Mstislav O ^a   Kazankova, Marina A ^a   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000383902     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017238s     Document Type: Article

References (31)

1. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. Omac, J. Application of Organometallic Compounds; Wiley: Toronto, 1999. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. N., Jordon, F., Stone, A., Wilkinson, J., Eds.; Pergamon Press: New York, 1995; Vola. 9 and 12. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York, 1999.
2. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. Omac, J. Application of Organometallic Compounds; Wiley: Toronto, 1999. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. N., Jordon, F., Stone, A., Wilkinson, J., Eds.; Pergamon Press: New York, 1995; Vola. 9 and 12. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York, 1999.
3. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. Omac, J. Application of Organometallic Compounds; Wiley: Toronto, 1999. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. N., Jordon, F., Stone, A., Wilkinson, J., Eds.; Pergamon Press: New York, 1995; Vola. 9 and 12. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York, 1999.
4. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. Omac, J. Application of Organometallic Compounds; Wiley: Toronto, 1999. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. N., Jordon, F., Stone, A., Wilkinson, J., Eds.; Pergamon Press: New York, 1995; Vola. 9 and 12. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York, 1999.
5. Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; VCH: New York, 1996. Homogeneous Catalysis with Metal-Phosphine Complexes; Pignolet, L. H., Ed.; Plenum Press: New York, 1983.
6. Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B.; Herrmann, W. A., Eds.; VCH: New York, 1996. Homogeneous Catalysis with Metal-Phosphine Complexes; Pignolet, L. H., Ed.; Plenum Press: New York, 1983.
7. Han, L.-B.; Mizaeri, F.; Zhao Ch.-Q.; Tanaka, M. J. Am. Chem. Soc. 2000, 122, 5407.
8. Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571.
9. For example, see: The Chemistry of Functional Groups - The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1990-1992. Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Denker: New York, 1992.
10. For example, see: The Chemistry of Functional Groups - The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley: Chichester, U.K., 1990-1992. Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Denker: New York, 1992.
11. Wolfsberger, W. Chem. Zeitung 1988, 112, 53.
12. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
13. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
14. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
15. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
16. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
17. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
18. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
19. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
20. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
21. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
22. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
23. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
24. 3 to a double bond is limited to Michael-type activated alkenes: Nagel, U.; Reigel, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223. Hoye, P. A. T.; Pringle, P. G.; Smith, M. B. J. Chem. Soc., Chem. Commun. 1990, 1701. Pringle, P. G.; Brewin, D.; Smith, M. B.; Worboys, K. In Aqueous Organometallic Chemistry and Catalysis; Horvath, I. T., Joo, F., Eds.; Dordrecht, The Netherlands, 1995; Vol. 5, p 111. Costa, E.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Chem. Soc., Dalton Trans. 1997, 4277. Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039. Costa, E.; Pringle, P. G.; Worboys, K. Chem. Commun. 1998, 49. Orpen, A. G.; Pringle, P. G.; Smith, M. B.; Worboys, K. J. Organomet. Chem. 1998, 550, 255. Wicht, D. K.; Kourkine, I. V.; Kovacik I.; Glueck, D. S.; Concolino, T. E.; Yap, G. P. A.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5381. Wicht, D. K.; Kovacik, I.; Glueck, D. S. Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L. Organometallics 1999, 18, 5141. Kovacik, I.; Wicht, D. K.; Grewal, N. S.; Glueck, D. S.; Incarvito, C. D.; Guzei, I. A.; Rheingold, A. L. Organometallics 2000, 19, 950. Hydrophosphination of an unactivated double bond by lanthanide catalysis: Douglass, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824. Takaki, K.; Takeda, M.; Koshoji, G.; Shishido, T.; Takehira, K. Tetrahedron Lett. 2001, 42, 6357. Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221.
25. Kazankova, M. A.; Efimova, I. V.; Kochetkov, A. N.; Afanas'ev, V. V.; Beletskaya I. P.; Dixneuf, P. H. Synlett 2001, 497.
26. 2 can be developed to a useful synthetic method. See also: Tunney, S. E.; Stille J. K. J. Org. Chem. 1987, 748.
27. Khachatryan, R. A.; Sayadyan, S. V.; Grigoryan, N. Yu.; Indzhikyan, M. G. J. Gen. Chem. USSR (Engl. Transl.) 1988, 58, 2197. Issleib, K.; Jasche, K Chem. Ber. 1967, 100, 412.
28. Khachatryan, R. A.; Sayadyan, S. V.; Grigoryan, N. Yu.; Indzhikyan, M. G. J. Gen. Chem. USSR (Engl. Transl.) 1988, 58, 2197. Issleib, K.; Jasche, K Chem. Ber. 1967, 100, 412.
29. Wang, H.-H.; Casalnuovo, A. L.; Johnson, B. J.; Huetig, A. M.; Pignolet, L. H. Inorg. Chem. 1988, 27, 325. Uhlig, V. E.; Maaser, M. Z. Z. Anorg. Allg. Chem. 1966, 344, 205.
30. Wang, H.-H.; Casalnuovo, A. L.; Johnson, B. J.; Huetig, A. M.; Pignolet, L. H. Inorg. Chem. 1988, 27, 325. Uhlig, V. E.; Maaser, M. Z. Z. Anorg. Allg. Chem. 1966, 344, 205.
31. 6) -15.8 (s).