The trans-chlorometalation of hetero-substituted alkynes: A facile entry to unsymmetrical palladium YCY′ (Y, Y′ = NR2, PPh2, OPPh2, and SR) "pincer" complexes

Organometallics

Volumn 21, Issue 15, 2002, Pages 3221-3227

  Ebeling, Gunter ^a   Meneghetti, Mario R ^a   Rominger, Frank ^b   Dupont, Jairton ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS; X RAY DIFFRACTION ANALYSIS;

TRANS-CHLOROMETALATION;

ORGANOMETALLICS;

EID: 0038002449     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om011002a     Document Type: Article

References (32)

1. For recent reviews see: (a) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759-762.
2. (b) Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 4, 1917-1927.
3. (c) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750-3781.
4. See for example: (a) Albrecht, M.; Kocks, B. M.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 2001, 624, 271-286.
5. (b) Beletskaya, I. P.; Chuchurjukin, A. V.; Dijkstra, H. P.; van Klink, G. P. M.; van Koten, G. Tetrahedron Lett. 2000, 41, 1075-1079.
6. (c) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619-1620.
7. (d) Bedford, R. B.; Draper, S. M.; Scully, P. N.; Welch, S. L. New J. Chem. 2000, 24, 745-747.
8. (e) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. L.; Dupont, J. Org. Lett. 2000, 2, 1287-1290.
9. (f) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y. S. J. Am. Chem. Soc. 1999, 121, 9531-9538.
10. (g) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379-7383.
11. (h) Steenwinkel, P.; Gossage, R. A.; Maunula, T.; Grove, D. M.; van Koten, G. Chem. Eur. J. 1998, 4, 763-768.
12. (i) Huck, W. T. S.; vanVeggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215.
13. (j) Loeb, S. J.; Shimizu, G. K. H. J. Chem. Soc., Chem. Commun. 1993, 1395-1397.
14. (l) Portnoy, M.; BenDavid, Y.; Milstein, D. Organometallics 1993, 12, 4734-4735.
15. (m) Haenel, M. W.; Jakubik, D.; Kruger, C.; Betz, P. Chem. Ber. 1991, 124, 333-336.
16. (n) Dupont, J.; Beydoun, N.; Pfeffer, M. J. Chem. Soc., Dalton Trans. 1989, 1715-1720.
17. (o) Rimml, H.; Venanzi, L. M. Phosphorus Sulfur 1987, 30, 297-300.
18. (p) Errington, J.; McDonald, W. S.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 2312-2314.
19. (q) Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020-1024.
20. (r) Dykstra, H. P.; Albrecht, M.; van Koten, G. Chem. Commun. 2002, 126-127.
21. Holton, R. A.; Sibi, M. P.; Murphy, W. S. J. Am. Chem. Soc. 1988, 110, 314-316.
22. - terdentate group see: Riera, X.; López, C.; Caubet, A.; Moreno, V.; Solans, X.; Font-Bardia, M. Eur. J. Inorg. Chem. 2001, 2135-2141, and references therein.
23. (a) Dupont, J.; Basso, N. R.; Meneghetti, M. R. Polyhedron 1996, 15, 2299-2302.
24. (b) Dupont, J.; Basso, N. R.; Meneghetti, M. R.; Konrath, R. A.; Burrow, R.; Horner, M. Organometallics 1997, 16, 2386-2391.
25. Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
26. Klusener, P. A. A.; Hanekamp, J. C.; Brandsma, L.; Schleyer, P. V. J. Org. Chem. 1990, 55, 1311-1321.
27. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
28. Orpen, A. G.; Brammer, L.; Allen, P. H.; Kennard, O.; Watson, D. G.; Robin Taylor, R. J. Chem. Soc., Dalton Trans 1989, S1-S83.
29. Calculations for the model systems A and B were performed with the Gaussian 98 program package: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzalez, C.; 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.5; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1981.
31. Sheldrick, Q. M. SADABS; Bruker AXS, Inc.: Madison, WI, 1996.
32. Sheldrick, G. M. SHELXTL V5.10; Bruker AXS, Inc.: Madison, WI, 1997.