Palladium-catalysed [3+2] cycloaddition of alk-5-ynylidenecyclopropanes to alkynes: A mechanistic DFT study

Chemistry - A European Journal

Volumn 14, Issue 1, 2008, Pages 272-281

  García Fandiño, Rebeca ^b   Gulías, Moisés ^b   Castedo, Luis ^b   Granja, Juan R ^b   Mascareñas, José L ^b   Cárdenas, Diego J ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alkynes; Carbocycles; Density functional calculations; Metallacycles; Palladium

Indexed keywords

AROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY; GIBBS FREE ENERGY; ISOMERS; PALLADIUM COMPOUNDS;

ALKYLIDENECYCLOPROPANES; ALKYNES; METALLACYCLES; OXIDATIVE ADDITION;

CYCLOADDITION;

ALKYNE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; METHANE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ELECTRON; METHYLATION; THERMODYNAMICS;

ALKYNES; CATALYSIS; CYCLIZATION; CYCLOPROPANES; ELECTRONS; METHANE; METHYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM; THERMODYNAMICS;

EID: 38049128689     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700973     Document Type: Article

References (32)

1. For reviews, see: a) L. A. Paquette, Top. Curr. Chem. 1984, 119, 1;
2. b) B. M. Trost, Chem. Soc. Rev. 1982, 11, 141-170;
3. c) Cyclopentanoid Terpene Derivatives (Organic Substances of Natural Origin) (Eds.: W. I. Taylor, A. R. Battersby), Vol. 2, M. Dekker. New York, 1969.
4. V. Singh. B. Thomas, Tetrahedron 1998, 54, 3647-3692.
5. For reviews on metal-promoted reactions of MCPs see: a) P. Binger, H. M. Büch, Top. Curr. Chem. 1987, 135, 77-151;
6. b) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49-92;
7. c) P. Binger, T. Schmidt in Houben-Weyl (Ed.: A. DeMeijere), Vol. E17c. Thieme, Stuttgart (Germany). 1997, pp. 2217-2294;
8. d) I. Nakamura, Y. Yamamoto, Adv. Synth. Catal. 2002, 344, 111-129;
9. e) for a review on related cycloadditions of trimethylenemethane complexes generated from bifunctional conjunctive reagents see: B. M. Trost. Angew. Chem. 1986, 98, 1-20;
10. Angew. Chem. Int. Ed. Engl. 1986, 25, 1-20.
11. a) S. A. Bapuji, W. B. Motherwell, M. Shipman. Tetrahedron Lett. 1989, 30, 7107-7110:
12. b) H. Corlay, R. T. Lewis, W. B. Motherwell, M. Shipman, Tetrahedron 1995, 51, 3303-3318.
13. a) M. Lautens, Y. Ren, P. H. M. Delanghe, J. Am. Chem. Soc. 1994, 116, 8821-8822;
14. b) M. Lautens, Y. Ren, J. Am. Chem. Soc. 1996, 118, 9597-9605.
15. A. Delgado, J. R. Rodríguez, L. Castedo, J. L. Mascareñas, J. Am. Chem. Soc. 2003, 125, 9282-9283.
16. T. Suzuki, H. Fujimoto. Inorg. Chem. 2000, 39, 1113-1119.
17. Gaussian 98 (Revision A. 11.3). M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr. R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam. A. D. Daniels. K. N. Kudin, M. C. Strain. O. Farkas, J. Tomasi, V. Barone. M. Cossi. R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu. A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, 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, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian. Inc., Pittsburgh PA. 2002.
18. Gaussian 03 (Revision C.01), 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, 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, J. A. Pople. Gaussian. Inc., Wallingford CT, 2004.
19. a) P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627;
20. b) W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 1996, 100, 12974-12980;
21. c) P.J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270-283;
22. d) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 284-298;
23. e) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310.
24. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5653;
25. b) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
26. c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
27. A. Sundermann, O. Uzan, J. M. L. Martin. Chem. Eur. J. 2001, 7, 1703-1711.
28. M. Gulías, J. L. Mascareñas, unpublished results.
29. Proximal oxidative addition would not lead to the desired products. The precedent mechanistic studies carried out by Fujimoto (see reference [7]) also favoured distal addition instead of a proximal one.
30. A. C. Albéniz, A. L. Casado, P. Espinet, Inorg. Chem. 1999, 38, 2510-2515.
31. Computational study on palladaene reactions of σ-allylpalladium complexes: M. García-Iglesias. E. Buñuel, D. J. Cárdenas. Organometallics 2006, 25, 3620-3627.
32. B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1982, 104, 3733-3735.