Pincer click ligands

Angewandte Chemie - International Edition

Volumn 47, Issue 24, 2008, Pages 4555-4558

  Schuster, Elaine M ^a   Botoshansky, Mark ^a   Gandelman, Mark ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Heck reaction; Homogeneous catalysis; Ligand design; Organometallic chemistry; Pincer ligands

Indexed keywords

CATALYSIS; CATALYSTS; CHELATION; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

HECK REACTION; HOMOGENEOUS CATALYSIS; LIGAND DESIGN; ORGANOMETALLIC CHEMISTRY; PINCER LIGANDS;

LIGANDS;

EID: 53549098809     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800123     Document Type: Article

References (36)

1. a) G. van Koten, M. Albrecht, Angew. Chem. 2001, 113, 3866;
2. Angew. Chem. Int. Ed. 2001, 40, 3750;
3. b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759.
4. For reviews, see a) J. T. Singleton, Tetrahedron 2003, 59, 1837;
5. b) D. Morales-Morales, Rev. Soc. Quim. Mex. 2004, 48, 338.
6. For examples, see a) M. Gandelman, A. Vigalok, L. J. W. Shimon, D. Milstein, Organometallics 1997, 16, 3981;
7. b) J.-F. Gong, Y.-H. Zhang, M.-P. Song, C. Xu, Organometallics 2007, 26, 6487.
8. G. Y. Li, P. J. Fagan, P. L. Watson, Angew. Chem. 2001, 113, 1140;
9. Angew. Chem. Int. Ed. 2001, 40, 1106;
10. for noncovalent approaches, see a) B. Breit, Angew. Chem. 2005, 117, 6976;
11. Angew. Chem. Int. Ed. 2005, 44, 6816;
12. b) J. M. Takacs, P. M. Hrvatin, J. M. Atkins, D. S. Reddy, J. L. Clark, New J. Chem. 2005, 29, 263;
13. c) V. F. Slagt, P. W. N. M. van Leeuwen, J. N. H. Reek, Angew. Chem. 2003, 115, 5777;
14. Angew. Chem. Int. Ed. 2003, 42, 5619;
15. d) V. F. Slagt, P. C. J. Kamer, P. W. N. M. van Leeuwen, H. N. J. Reek, J. Am. Chem. Soc. 2004, 126, 4056.
16. R. Huisgen, Proc. Chem. Soc. 1961, 357.
17. a) V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708;
18. Angew. Chem. Int. Ed. 2002, 41, 2596;
19. b) H. C. Kolb, M. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. Angew Chem. Int. Ed. 2001, 40, 2004.
20. a) H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128;
21. b) V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51.
22. a) Q. Dai, W. Gao, D. Liu, L. M. Kapes, X. Zhang, J. Org. Chem. 2006, 71, 3928;
23. b) R. D. Detz, S. Heras, R. de Gelder, P. W. N. M. van Leeuwen, H. Hiemstra, J. N. H. Reek, J. H. van Maarseveen, Org. Lett. 2006, 8, 3227;
24. c) F. Dolhem, M. J. Johansson, T. Antonsson, N. Kann, J. Comb. Chem. 2007, 9, 477.
25. For synthetic details and characterization of the described compounds, see the Supporting Information.
26. P. Vedrenne, V. Le Guen, L. Toupet, T. Le Gall, C. Mioskowski, J. Am. Chem. Soc. 1999, 121, 1090.
27. H. Fritzsche, U. Hasserodt, F. Korte, G. Friese, K. Adrian, H. J. Arenz, Chem. Ber. 1964, 97, 1988.
28. For selected examples, see a) G. Shaw, H. Wamhoff, R. N. Butler in Comprehensive Heterocyclic Chemistry, Vol. 5 (Eds.: A. L. Katritzky, C. W. Rees, K. T. Potts), Pergamon, Oxford, 1984, chap. 4.11;
29. b) T. L. Mindt, H. Struthers, L. Brans, T. Anguelov, C. Schweinsberg, V. Maes, D. Tourwe, R. Schibli, J. Am. Chem. Soc. 2006, 128, 15096;
30. c) B. M. J. M. Suijkerbuijk, B. N. H. Aerts, H. P. Dijkstra, M. Lutz, A. L. Spek, G. van Koten, R. J. M. Klein Gebbink, Dalton Trans. 2007, 1273, and Ref. [7] therein;
31. d) J. C. Huffman, A. H. Flood, Y. Li, Chem. Commun. 2007, 2692.
32. CCDC 673968 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.
33. a) R. F. Heck in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, chap. 4.3;
34. b) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
35. a) For PCP systems, see M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687;
36. b) for the use of SCS systems in Heck chemistry, see D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531.