Hydrosilylation of alkynes with a cationic rhodium species formed in an anionic micellar system

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2217-2220

  Sato, Akinori ^a   Kinoshita, Hidenori ^a   Shinokubo, Hiroshi ^a,b   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; RHODIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DISSOCIATION; HYDROSILYLATION; MICELLIZATION; REACTION ANALYSIS;

EID: 3142706593     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049308b     Document Type: Article

References (35)

1. Motoda, D.; Kinoshita, H.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 1860.
2. (a) Suginome, M.; Ito, Y. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: Chichester, 1995; p 426.
3. (b) Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1971, 93, 3090.
4. For the use of surfactants in organic synthesis, see: Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
5. For transition metal-catalyzed reactions in aqueous media, see: (a) Sinou, D. In Modern Solvent in Organic Synthesis; Knochel, P., Ed.; Springer-Verlag: Berlin, 1999; p 41. (b) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry; Wiley-VCH: Weinheim, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997.
6. For transition metal-catalyzed reactions in aqueous media, see: (a) Sinou, D. In Modern Solvent in Organic Synthesis; Knochel, P., Ed.; Springer-Verlag: Berlin, 1999; p 41. (b) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry; Wiley-VCH: Weinheim, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997.
7. For transition metal-catalyzed reactions in aqueous media, see: (a) Sinou, D. In Modern Solvent in Organic Synthesis; Knochel, P., Ed.; Springer-Verlag: Berlin, 1999; p 41. (b) Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Chemistry; Wiley-VCH: Weinheim, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley: New York, 1997.
8. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
9. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
10. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
11. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
12. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
13. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
14. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
15. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
16. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
17. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
18. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
19. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
20. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
21. For recent examples of rhodium-catalyzed reactions in aqueous media, see: (a) Dwars, T.; Oehme, G. Adv. Synth. Catal. 2002, 344, 239. (b) Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Angew. Chem., Int. Ed. 1998, 37, 2851. (c) Selke, R.; Holz, J.; Riepe, A.; Börner, A. Chem. Eur. J. 1998, 4, 769. (d) Ludwig, M.; Kadyrov, R.; Fiedler, H.; Haage, K.; Selke, R. Chem. Eur. J. 2001, 7, 3298. (e) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem., Int. Ed. 2003, 42, 2409. (f) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784. (g) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (h) Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 2409. (i) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722. (j) Yonehara, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 9381. (k) Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C.-J. J. Am. Chem. Soc. 2001, 123, 7451. (l) Amengual, R.; Michelet, V.; Genêt, J.-P. Tetrahedron Lett. 2002, 43, 5905. (m) Amengual, R.; Michelet, V.; Genêt, J.-P. Synlett 2002, 1791. (n) Pucheault, M.; Darses, S.; Genêt, J.-P. Eur. J. Org. Chem. 2002, 3552.
22. (a) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, Chapter 3.12.
23. (b) Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organosilicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 2, Chapter 29.
24. (c) Corey, J. Y. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI: Greenwich, 1991; Vol. 1, p 355.
25. (d) Marciniec, B. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, 1992.
26. Hydrosilylation in aqueous media has been reported recently, (a) Wu, W.; Li, C. J. Chem. Commun. 2003, 1668. (b) Motoda, D.; Shinokubo, H.; Oshima, K. Synlett 2002, 1529.
27. Hydrosilylation in aqueous media has been reported recently, (a) Wu, W.; Li, C. J. Chem. Commun. 2003, 1668. (b) Motoda, D.; Shinokubo, H.; Oshima, K. Synlett 2002, 1529.
28. (a) Takeuchi, R.; Tanouchi, N. J. Chem. Soc., Chem. Commun. 1993, 1319.
29. (b) Takeuchi, R.; Tanouchi, N. J. Chem. Soc., Perkin Trans, 1 1994, 2909.
30. (c) Takeuchi, R.; Nitta, S.; Watanabe, D. J. Org. Chem. 1995, 60, 3045.
31. (a) Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127.
32. (b) Ojima, I.; Kumagai, M.; Nagai, Y. J. Organomet. Chem. 1974, 66, C14.
33. (c) Doyle, M. P.; High, K. G.; Nesloney, C. L.; Clayton, T. W., Jr.; Lin, J. Organometallics 1991, 10, 1225.
34. -3 M.
35. Mori, A.; Takahashi, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443.