Rhodium-catalyzed addition of arylboronic acids to alkynyl aza-heteroaromatic compounds in water

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 762-769

  Lautens, Mark ^a   Yoshida, Masahiro ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS;

CATALYSIS; CATALYSTS; CHELATION; OLEFINS;

ORGANIC ACIDS;

ALKENE; ALKYNYL GROUP; AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; LIGAND; NITROGEN; PHOSPHINE; PYRIDINE DERIVATIVE; RHODIUM; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0037423347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0205255     Document Type: Article

References (67)

1. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
2. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
3. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
4. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
5. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
6. For reviews of organic synthesis in water, see: (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998. (b) Li, C. J.; Chan, T. H. Organic Reactions in Organic Media; John Wiley and Sons: New York, 1997. (c) Cornils, B.; Herrmann, W. A. Aqueous Phase Organometallic Chemistry: Concepts and Applications; Wiley-VCH: Weinheim, 1998. (d) Li, C. J. Chem. Rev. 1993, 93, 2023. (e) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149. (f) Li, C. J. Tetrahedron 1996, 52, 5643.
7. For review of water-soluble ligands, see: (a) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (b) Joó, F.; Kathó, A. J. Mol. Catal. A 1997, 116, 3. (c) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9. (d) Genet, J. P.; Saignac, M. J. Organomet. Chem. 1999, 576, 305. (e) Genet, J. P.; Saignac, M.; Lemaire-Audoire, S. In Transition Metal Catalysed Reactions; Murahashi, S.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999; p 55.
8. For review of water-soluble ligands, see: (a) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (b) Joó, F.; Kathó, A. J. Mol. Catal. A 1997, 116, 3. (c) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9. (d) Genet, J. P.; Saignac, M. J. Organomet. Chem. 1999, 576, 305. (e) Genet, J. P.; Saignac, M.; Lemaire-Audoire, S. In Transition Metal Catalysed Reactions; Murahashi, S.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999; p 55.
9. For review of water-soluble ligands, see: (a) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (b) Joó, F.; Kathó, A. J. Mol. Catal. A 1997, 116, 3. (c) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9. (d) Genet, J. P.; Saignac, M. J. Organomet. Chem. 1999, 576, 305. (e) Genet, J. P.; Saignac, M.; Lemaire-Audoire, S. In Transition Metal Catalysed Reactions; Murahashi, S.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999; p 55.
10. For review of water-soluble ligands, see: (a) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (b) Joó, F.; Kathó, A. J. Mol. Catal. A 1997, 116, 3. (c) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9. (d) Genet, J. P.; Saignac, M. J. Organomet. Chem. 1999, 576, 305. (e) Genet, J. P.; Saignac, M.; Lemaire-Audoire, S. In Transition Metal Catalysed Reactions; Murahashi, S.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999; p 55.
11. For review of water-soluble ligands, see: (a) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (b) Joó, F.; Kathó, A. J. Mol. Catal. A 1997, 116, 3. (c) Katti, K. V.; Gali, H.; Smith, C. J.; Berning, D. E. Acc. Chem. Res. 1999, 32, 9. (d) Genet, J. P.; Saignac, M. J. Organomet. Chem. 1999, 576, 305. (e) Genet, J. P.; Saignac, M.; Lemaire-Audoire, S. In Transition Metal Catalysed Reactions; Murahashi, S.; Davies, S. G., Eds.; Blackwell Science: Oxford, 1999; p 55.
12. These ligands are commercially available from Strem Chemicals.
13. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
14. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
15. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
16. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
17. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
18. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
19. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
20. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
21. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
22. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
23. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
24. For recent representative reactions using TPPTS: (a) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1985, 26, 6337. (b) Mignani, G.; Morel, D.; Colleuille, Y. Tetrahedron Lett. 1986, 27, 2591. (c) Grosselin, J. M.; Mercier, C.; Allmang, G.; Grass, F. Organometallics 1991, 10, 2126. (d) Genet, J. P.; Linquist, A.; Blard, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443. (e) Amatore, C.; Blart, E.; Genet, J. P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829. (f) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1997, 38, 8695. (g) Galland, J.-C.; Savignac, M.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 2323. (h) Bhanage, B. M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427. (i) Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845. (j) Michelet, V.; Galland, J.-C.; Charruault, L.; Savignac, M.; Genet, J.-P. Org. Lett. 2001, 3, 2065. (k) Dupuis, C.; Adiey, K.; Charruault, L.; Michelet, V.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 2001, 42, 6523. (l) Francisco, L. W.; Moreno, D. A.; Atwood, J. D. Organometallics 2001, 20, 4237.
25. For reactions using TPPDS, see: (a) Thorpe, T.; Brown, S. M.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2000, 41, 4503. (b) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (c) Chen, H.; Li, Y.; Chen, J.; Cheng, P.; Li, X. Catal. Today 2002, 74, 131.
26. For reactions using TPPDS, see: (a) Thorpe, T.; Brown, S. M.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2000, 41, 4503. (b) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (c) Chen, H.; Li, Y.; Chen, J.; Cheng, P.; Li, X. Catal. Today 2002, 74, 131.
27. For reactions using TPPDS, see: (a) Thorpe, T.; Brown, S. M.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2000, 41, 4503. (b) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358. (c) Chen, H.; Li, Y.; Chen, J.; Cheng, P.; Li, X. Catal. Today 2002, 74, 131.
28. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
29. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
30. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
31. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
32. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
33. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
34. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
35. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
36. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
37. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
38. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
39. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
40. For representative other examples of transition metal chemistry of water-soluble phosphine, see: (a) Smith, R. T.; Ungar, R. K.; Sanderson, L. J.; Baird, M. C. Organometallics 1983, 2, 1138. (b) Darensbourg, D. J.; Joo, F.; Kannisto, M.; Katho, A.; Reibenspies, J. H. Organometallics 1992, 11, 1990. (c) Tóth, I.; Hanson, B. E. Organometallics 1993, 12, 1506. (d) Jones, A.; Roberts, D. L.; Davis, M. E. Nature 1994, 370, 449. (e) Ding, H.; Hanson, B. E.; Bakos, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1645. (f) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317. (g) Shin, S.; RajanBabu, T. V. Org. Lett. 1999, 1, 1229. (h) Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 5593. (i) Kovacs, J.; Todd, T. D.; Reibenspies, J. H.; Joo, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963. (j) Ueda, M.; Nishimura, M.; Miyaura, N. Synlett, 856. (k) Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757. (l) Lucey, D. M.; Atwood, J. D. Organometallics 2002, 21, 2105. (m) Raghuraman, K.; Pillarsetty, N.; Volkert, W. A.; Barnes, C.; Jurisson, S.; Katti, K. V. J. Am. Chem. Soc. 2002, 124, 7276.
41. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
42. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
43. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
44. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
45. For additions to enones, see: (a) Sakai, M.; Hayashi, M.; Miyaura, N. Organometallics 1997, 16, 4229. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579. For additions to α,β-unsaturated esters, see: (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951. For additions to vinyl phosphonates, see: (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591. For additions to vinyl nitro compounds, see: (e) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
46. Recently, Brown reported ruthenium-catalyzed oxidative Heck reactions of arylboronic acids to activated alkenes: Farrington, E. J.; Brown, J. M.; Barnard, C. F. J.; Rowsell, E. Angew. Chem., Int. Ed. 2002, 41, 169.
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