Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction

Canadian Journal of Chemistry

Volumn 86, Issue 5, 2008, Pages 410-415

  Gottardo, Christine ^a   Kraft, Thomas M ^a   Hossain, M Selim ^a   Zawada, Peter V ^a   Muchall, Heidi M ^b  

^a LAKEHEAD UNIVERSITY   (Canada)

^b Dept of Electrical and Computer Engineering   (Canada)

Author keywords

Competitive reactions; Hammett correlation; Sonogashira

Indexed keywords

COMPUTATIONAL METHODS; CORRELATION METHODS; FREE ENERGY; RATE CONSTANTS; SUBSTITUTION REACTIONS;

COMPETITIVE REACTIONS; HAMMETT CORRELATION; SONOGASHIRA;

REACTION KINETICS;

EID: 43949145599     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V08-038     Document Type: Article

References (28)

1. K. Sonogashira, Y. Tohda, and K. Hagihara. Tetrahedron Lett. 16, 4467 (1975).
2. E. Negishi and L. Anastasia. Chem. Rev. 103, 1979 (2003).
3. R. Chinchilla and C. Nájera. Chem. Rev. 107, 874 (2007).
4. S. Thorand and N. Krause. J. Org. Chem. 63, 8551 (1998).
5. R.D. Stephens and C.E. Castro. J. Org. Chem. 28, 3313 (1963).
6. S. Takashi, Y. Kuroyama, K. Sonogashira and N. Hagihara. Synthesis, 627 (1980).
7. J.-F. Fauvarque, F. Pfluger, and M. Troupel. J. Organomet. Chem. 208, 419 (1981).
8. C. Amatore and F. Pfluger. Organometallics, 9, 2276 (1990).
9. D. Zim, V.R. Lando, J. Dupont, and A.L. Monteiro. Org. Lett. 3, 3049 (2001).
10. S. Saito, S. Oh-tani, and N. Miyaura. J. Org. Chem. 62, 8024 (1997).
11. R. Benhaddou, S. Czernecki, G. Ville, and A. Zegar. Organometallics, 7, 2435 (1988).
12. A.S. Gruber, D. Zim, G. Ebeling, A.L. Monteiro, and J. Dupont. Org. Lett. 2, 1287 (2000).
13. D. Milstein and J.K. Stille. J. Am. Chem. Soc. 101, 4992 (1979).
14. H. Weissman and D. Milstein. Chem. Commun. 1901 (1999).
15. R. Ugo, A. Pasini, A. Fusi, and S. Cenini. J. Am. Chem. Soc. 94, 7364 (1972).
16. R.J, Mureinik, M. Weitzberg, and J. Blum. Inorg. Chem. 18, 915 (1979).
17. C. Gottardo and A. Aguirre. Tetrahedron Lett. 43, 7091 (2002).
18. R.F.W. Bader. Atoms in molecules: A quantum theory. Clarendon Press, Oxford, UK. 1990.
19. Substituent constants were taken from: (a) C. Hansch, A. Leo, and R.W. Taft. Chem. Rev. 91, 165 (1991);
20. (b) D.H. McDaniel and H.C. Brown, J. Org. Chem., 23, 420 (1958).
21. R.F.W. Bader and C. Chang. J. Phys. Chem. 93, 2946 (1989).
22. F.R. Hartley. The chemistry of platinum and palladium: with particular reference to complexes of the elements. John Wiley & Son, New York. 1973.
23. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo. R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson. W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople. Gaussian 03 [computer program], Revision C.02. Gaussian, Inc., Wallingford CT. 2004.
24. J.P. Perdew, K. Burke, and M. Ernzerhof. Phys. Rev. Lett. 77, 3865 (1996).
25. J.P. Perdew, K. Burke, and M. Ernzerhof. Phys. Rev. Lett., 78, 1396 (1997).
26. J.P. Perdew, M. Ernzerhof, and K.Burke. J. Chem. Phys. 105, 9982 (1996).
27. R.E. Easton, D.J. Giesen, A. Welch, C.J. Cramer, and D.G. Truhlar. Theor. Chim. Acta 93, 281 (1996).
28. Available from Professor R.F.W. Bader, McMaster University, Hamilton, ON L8S 4M1, Canada, and from the AIMPAC website (www.chemistry.mcmaster.ca/aimpac, last accessed on February 6, 20(58).