Selenium-ligated palladium(II) complexes as highly active catalysts for carbon-carbon coupling reactions: The Heck reaction

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2997-2999

  Yao, Qingwei ^a   Kinney, Elizabeth P ^a   Zheng, Chong ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHORUS DERIVATIVE; SELENIUM DERIVATIVE; SULFUR DERIVATIVE;

AIR; ARTICLE; CATALYSIS; HECK REACTION; OXIDATION; SYNTHESIS;

CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; SELENIUM;

EID: 4444234854     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0486977     Document Type: Article

References (29)

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25. Leading reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) Dupont, J.; Pfeffer, M. Spencer, M. Eur. J. Inorg. Chem. 2001, 1917. (c) Bedford, R. B. Chem. Commun. 2003, 1787. (d) van der Boom M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. Selected recent examples: (e) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Priermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357. (f) Gibson, S.; Foster, D. F.; Eastam, G. R.; Tooze, R. P.; Cole-Hamilton, D. J. Chem. Commun. 2001, 779. (g) Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (h) Gruber, A. S.; Zim, D. Z.; Ebeling, G.; Monteriro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (i) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. J. Am. Chem. Soc. 2000, 122, 9058.
26. Leading reviews: (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750. (b) Dupont, J.; Pfeffer, M. Spencer, M. Eur. J. Inorg. Chem. 2001, 1917. (c) Bedford, R. B. Chem. Commun. 2003, 1787. (d) van der Boom M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759. Selected recent examples: (e) Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Priermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357. (f) Gibson, S.; Foster, D. F.; Eastam, G. R.; Tooze, R. P.; Cole-Hamilton, D. J. Chem. Commun. 2001, 779. (g) Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687. (h) Gruber, A. S.; Zim, D. Z.; Ebeling, G.; Monteriro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287. (i) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. J. Am. Chem. Soc. 2000, 122, 9058.
27. Gruber, A. S.; Pozebon, D.; Monteriro, A. L.; Dupont, J. Tetrahedron Lett. 2001, 42, 7345.
28. See Supporting Information for a detailed comparison in activity between catalysts 1-3 and their sulfur and phosphorus analogues.
29. 4 gave much lower yield for this reaction, cf. entries 1-3, Table 2.