Mizoroki-Heck arylation of α,β-unsaturated acids with a hybrid fluorous ether, F-626: Facile filtrative separation of products and efficient recycling of a reaction medium containing a catalyst

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 8105-8107

  Fukuyama, Takahide ^a   Arai, Masashi ^a   Matsubara, Hiroshi ^a   Ryu, Ilhyong ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; ETHERS; FILTRATION; PALLADIUM COMPOUNDS; SEPARATION; SOLVENTS; UNSATURATED COMPOUNDS;

CARBENE COMPLEX; FILTRATES; MIZOROKI-HECK ARYLATION; UNSATURATED ACIDS;

CARBOXYLIC ACIDS;

CARBENOID; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; FLUOROUS ETHER; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYST; CHEMICAL REACTION; FILTRATION; HECK REACTION; MIZOROKI HECK ARYLATION; RECYCLING; SEPARATION TECHNIQUE;

EID: 8644236563     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049028+     Document Type: Article

References (48)

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38. Also see recent examples: (c) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348. (d) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617, 616. (e) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (f) Fukuyama, T.; Shinmen, M. Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (g) McLachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350.
39. Also see recent examples: (c) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348. (d) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617, 616. (e) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (f) Fukuyama, T.; Shinmen, M. Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (g) McLachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350.
40. Also see recent examples: (c) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348. (d) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617, 616. (e) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (f) Fukuyama, T.; Shinmen, M. Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (g) McLachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350.
41. Also see recent examples: (c) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 1999, 585, 348. (d) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C.-P.; Weskamp, T. J. Organomet. Chem. 2001, 617, 616. (e) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411. (f) Fukuyama, T.; Shinmen, M. Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691. (g) McLachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350.
42. 5 are active species in our system, we carried out mercury poisoning experiments by addition of mercury(0) (12.5: 1, Hg/Pd) to the reaction system. The addition of mercury(0) did not suppress the catalysis, which suggests the nanoparticles are not key species in the present system. For recent examples for the Heck reaction promoted by Pd nanoparticles, see: (a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Hendrickes, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285. (b) Consorti, C.; Zanini, M. L.; Leal, S.; Eberling, G.; Dupont, J. Org. Lett. 2003, 5, 983. (c) Nowotny, M.; Hanefeld, U.; van Konigsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. See also ref 11.
43. 5 are active species in our system, we carried out mercury poisoning experiments by addition of mercury(0) (12.5: 1, Hg/Pd) to the reaction system. The addition of mercury(0) did not suppress the catalysis, which suggests the nanoparticles are not key species in the present system. For recent examples for the Heck reaction promoted by Pd nanoparticles, see: (a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Hendrickes, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285. (b) Consorti, C.; Zanini, M. L.; Leal, S.; Eberling, G.; Dupont, J. Org. Lett. 2003, 5, 983. (c) Nowotny, M.; Hanefeld, U.; van Konigsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. See also ref 11.
44. 5 are active species in our system, we carried out mercury poisoning experiments by addition of mercury(0) (12.5: 1, Hg/Pd) to the reaction system. The addition of mercury(0) did not suppress the catalysis, which suggests the nanoparticles are not key species in the present system. For recent examples for the Heck reaction promoted by Pd nanoparticles, see: (a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Hendrickes, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285. (b) Consorti, C.; Zanini, M. L.; Leal, S.; Eberling, G.; Dupont, J. Org. Lett. 2003, 5, 983. (c) Nowotny, M.; Hanefeld, U.; van Konigsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. See also ref 11.
45. Cinnamic acid (3a) was also obtained by washing the precipitates with 2 M HCl aqueous solution instead of organic/aqueous biphasic workup. See the Experimental Section.
46. For Mizoroki-Heck reaction using phosphine-free carbene complexes, see: (a) Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. See also ref 13a,b.
47. For Mizoroki-Heck reaction using phosphine-free carbene complexes, see: (a) Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123. (b) Selvakumar, K.; Zapf, A.; Beller, M. Org. Lett. 2002, 4, 3031. See also ref 13a,b.
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