Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1845-1848

  Brice, Jodie L ^a   Meerdink, James E ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BIPHENYL; CARBAMIC ACID; ETHER; NITROGEN; PALLADIUM; PHENANTHROLINE DERIVATIVE; SULFONAMIDE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; SYNTHESIS;

EID: 84961983732     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494360     Document Type: Article

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54. d (DPCM) with the specified dielectric of 4.355 corresponding to a diethyl ether reaction medium. Optimized structures were verified to be at a local minimum by calculation of the harmonic vibrational frequencies, (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3101. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 10; Gaussian, Inc.: Pittsburgh, PA, 2001. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. (e) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245. (f) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996. 255, 327-335.
55. d (DPCM) with the specified dielectric of 4.355 corresponding to a diethyl ether reaction medium. Optimized structures were verified to be at a local minimum by calculation of the harmonic vibrational frequencies, (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3101. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 10; Gaussian, Inc.: Pittsburgh, PA, 2001. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. (e) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245. (f) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996. 255, 327-335.
56. d (DPCM) with the specified dielectric of 4.355 corresponding to a diethyl ether reaction medium. Optimized structures were verified to be at a local minimum by calculation of the harmonic vibrational frequencies, (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3101. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 10; Gaussian, Inc.: Pittsburgh, PA, 2001. (d) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. (e) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245. (f) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996. 255, 327-335.
57. d (DPCM) with the specified dielectric of 4.355 corresponding to a diethyl ether reaction medium. Optimized structures were verified to be at a local minimum by calculation of the harmonic vibrational frequencies, (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3101. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 10; Gaussian, Inc.: Pittsburgh, PA, 2001. (d) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. (e) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245. (f) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996. 255, 327-335.
58. d (DPCM) with the specified dielectric of 4.355 corresponding to a diethyl ether reaction medium. Optimized structures were verified to be at a local minimum by calculation of the harmonic vibrational frequencies, (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3101. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789. (c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 10; Gaussian, Inc.: Pittsburgh, PA, 2001. (d) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129. (e) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245. (f) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996. 255, 327-335.
59. For examples of palladium-catalyzed aminal formation (i.e., hydroamination of vinyl ethers), see: (a) Baig, T.; Jenck, J.; Kalck, P. J. Chem. Soc., Chem. Commun. 1992, 1552-1553. (b) Cheng, X.; Hu, K. K. Tetrahedron 2001, 57, 5445-5450.
60. For examples of palladium-catalyzed aminal formation (i.e., hydroamination of vinyl ethers), see: (a) Baig, T.; Jenck, J.; Kalck, P. J. Chem. Soc., Chem. Commun. 1992, 1552-1553. (b) Cheng, X.; Hu, K. K. Tetrahedron 2001, 57, 5445-5450.
61. Jung, Y. C.; Mishra, R. K.; Yoon, C. H.; Jung, K. W. Org. Lett. 2003, 5, 2231-2234.
62. Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188-7189.
63. Ackerman, L. J.; Sadighi, J. P.; Kurtz, D. M.; Labinger, J. A.; Bercaw, J. E. Organometallics 2003, 22, 3884-3890.
64. The commercial source of 3 (Aldrich) consists of ∼2.5:1 ratio of the cis- and trans-isomers. The relative reactivity of the two isomers is not readily apparent. Such analysis is complicated by the use of a large excess of 3 in the reaction (20-fold excess), side reactions that consume 3 (e.g., eqs 5 and 6), and the possibility of Pd-catalyzed equilibration of the isomers under the reaction conditions via transvinylation with the alcohol product (cf. eq 3).