Hydrogenation and dehalogenation under aqueous conditions with an amphiphilic-polymer-supported nanopalladium catalyst

Organic Letters

Volumn 7, Issue 1, 2005, Pages 163-165

  Nakao, Ryu ^a   Rhee, Hakjune ^a,b   Uozumi, Yasuhiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMPHOPHILE; MACROGOL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYMER; POLYSTYRENE; RESIN;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHLORINATION; DEHYDROGENATION; HYDROGENATION;

EID: 12344259935     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047670k     Document Type: Article

References (40)

1. For reviews on aqueous switching, see: (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-VCH: New York, 1997. (b) Grieco, P. A., Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (d) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
2. For reviews on aqueous switching, see: (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-VCH: New York, 1997. (b) Grieco, P. A., Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (d) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
3. For reviews on aqueous switching, see: (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-VCH: New York, 1997. (b) Grieco, P. A., Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (d) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
4. For reviews on aqueous switching, see: (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-VCH: New York, 1997. (b) Grieco, P. A., Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524. (d) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
5. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
6. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
7. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
8. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
9. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
10. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
11. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
12. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
13. (a) For reviews on heterogeneous switching, see: Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (g) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (h) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (i) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (j) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
14. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
15. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
16. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
17. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
18. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
19. For examples of aquacatalytic organic transformations with amphiphilic polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919. (b) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (c) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (d) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (e) Uozumi, Y. J. Synth. Org. Chem. Jpn. 2003, 60, 1063. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, Org. Lett. 2004, 6, 281.
20. For reviews, see: (a) Králik, M.; Biffis. A. J. Mol. Catal. A 2001, 177, 113. (b) Corain, B.; Králik, M. J. Mol. Catal. A 2001, 173, 99.
21. For reviews, see: (a) Králik, M.; Biffis. A. J. Mol. Catal. A 2001, 177, 113. (b) Corain, B.; Králik, M. J. Mol. Catal. A 2001, 173, 99.
22. Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
23. ARP is the abbreviation for Amphiphilic Resin-dispersion of nano-Particles.
24. 1% DVB cross-linked, average diameter of polymer beads = 170 μm, average diameter of palladium particle = 9.0 nm, palladium loading = 0.4 mmol/g.
25. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
26. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
27. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
28. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
29. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
30. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
31. For several examples of polymer-stabilized palladium nanoparticles, see: (a) Ley, S. V. Mitchell, C.; Pears, D.; Ramarao, C.; Yu, J.-Q.; Zhou, W. Org. Lett. 2003, 5, 4665. (b) Bremeyer, N.; Ley, S. V.; Ramarao, C.; Shirley, I. M.; Smith, S. C. Synlett 2002, 1843. (c) Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I. F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134. (d) Yu, J.-Q.; Wu, H.-C.; Ramarao, C.; Spenver, J. B.; Ley, S. V. Chem. Commun. 2002, 678. (e) Toshima, N.; Shiraishi, Y.; Teranishi, T.; Miyake, M.; Tominaga, T.; Watanabe, H.; Brijoux, W.; Bönemann, H.; Schmid, G. Appl. Organomet. Chem. 2001, 15, 178. (f) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594. (g) Bergbreiter, D. E.; Chen, B.; Lynch, T. J. J. Org. Chem. 1983, 48, 4179.
32. For a review, see: Alonso, F.; Beletskaya, I. P.; Yus. M. Chem. Rev. 2002, 102, 4009.
33. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
34. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
35. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
36. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
37. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
38. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
39. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.
40. For recent examples of palladium-mediated hydrodechlorination of chloroarenes, see: (a) Kang, R.; Ouyang, X.; Han, J.; Zhen, X. J. Mol. Catal. A 2001, 175, 153. (b) Desmarets, C.; Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2002, 21, 1554. (c) Maleczka, R. E., Jr.; Rahaim, R. J., Jr.; Teixeira, R. R. Tetrahedron Lett. 2002, 43, 7087. (d) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetrahedron Lett. 2002, 43, 7247. (e) Sajiki, H.; Kume, A.; Hattori, K.; Nagase, H.; Hirota, K. Tetrahedron Lett. 2002, 43, 7251. (f) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.; Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191. (g) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173. (h) Selvam, P.; Sonavane, S. U.; Mohapatra, S. K.; Jayaram, R. V. Tetrahedron Lett. 2004, 45, 3071.