Improved one-pot synthesis of C3-symmetric clickphos and related ligands: Structures of unique triazole-zinc complexes

European Journal of Organic Chemistry

Volumn , Issue 8, 2011, Pages 1432-1437

  Zink, Daniel M ^a,b   Baumann, Thomas ^b   Nieger, Martin ^c   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b CYNORA GMBH   (Germany)

^c UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Click chemistry; ClickPhos; Helical structures; Triazole; Zinc

Indexed keywords

EID: 79952151950     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001505     Document Type: Article

References (39)

1. For example, palladium catalysis
2. E. M. Schuster, M. Botoshansky, M. Gandelman, Organometallics 2009, 28, 7001-7005.
3. D. Popa, R. Marcos, S. Sayalero, A. Vidal-Ferran, M. A. Pericas, Adv. Synth. Catal. 2009, 351, 1539-1556.
4. E. M. Schuster, M. Botoshansky, M. Gandelman, Angew. Chem. 2008, 120, 4631
5. Angew. Chem. Int. Ed. 2008, 47, 4555-455.
6. R. J. Detz, S. Arevalo Heras, R. De Gelder, P. W. N. M. Van Leeuwen, H. Hiemstra, J. N. H. Joon, Inorg. Chim. Acta 2002, 330, 38-43.
7. D. Liu, W. Gao, Q. Dai, X. Zhang, Org. Lett. 2005, 7, 4907-4910.
8. Q. Dai, W. Gao, D. Liu, L. M. Kapes, X. Zhang, J. Org. Chem. 2006, 71, 3928-3934.
9. H. Oki, I. Oura, T. Nakamura, K. Ogata, S. Fukuzawa, Tetrahedron: Asymmetry 2009, 20, 2185-2191.
10. M. Kato, T. Nakamura, K. Ogata, S. Fukuzawa, Eur. J. Org. Chem. 2009, 5232-5238.
11. M. Kato, H. Oki, K. Ogata, S. Fukuzawa, Synlett 2009, 1299-1302.
12. S. Fukuzawa, H. Oki, Org. Lett. 2008, 10, 1747-1750.
13. S. Fukuzawa, H. Oki, M. Hosaka, J. Sugasawa, S. Kikuchi, Org. Lett. 2007, 9, 5557-5560.
14. F. Dolhem, M. J. Johansson, T. Antonsson, N. Kann, J. Comb. Chem. 2007, 9, 477-486.
15. A. Krasinski, V. V. Fokin, K. B. Sharpless, Org. Lett. 2004, 6, 1237-1240.
16. S. G. A. van Assema, C. G. J. Tazelaar, G. B. de Jong, J. H. van Maarseveen, M. Schakel, M. Lutz, A. L. Spek, J. C. Slootweg, K. Lammertsma, Organometallics 2008, 27, 3210-3215.
17. A. L. Rheingold, L. M. Liable-Sands, S. Trofimenko, Angew. Chem. 2000, 112, 3459
18. Angew. Chem. Int. Ed. 2000, 39, 3321-3324.
19. A. L. Rheingold, L. M. Liable-Sands, S. Trofimenko, Inorg. Chim. Acta 2002, 330, 38-43.
20. [2] "It is worthy of note that the ligand synthesis could be shortened into a one-pot operation with comparable crude yield of the desired product by directly quenching the intermediate 5 with a chlorophosphane. The isolation of triazole 6 prior to installation of the phosphanyl substituents is solely because of the ease of purification of the final phosphane ligands." We did not observe any problems during purification.
21. SAFETY: Whereas ionic azides such as sodium azide are relatively stable, carbon-bound or heavy-metal azides are subject to thermal-sometimes explosive-decomposition. Some organic and other covalent azides are classified as toxic and highly explosive, and appropriate safety measures must be taken at all times:, S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. 2005, 117, 5320; Angew. Chem. Int. Ed. 2005, 44, 5188.
22. 3 is toxic, with a concentration of 600 ppm being lethal in just a few minutes. It is classified as very toxic and corrosive under EU Directive 67/548/EEC, and the risk phrases R14, R26/28, R35 and R48/20 are obligatory.
23. For a review:, I. Kuzu, I. Krummenacher, J. Meyer, F. Armbruster, F. Breher, Dalton Trans. 2008, 5836-5865.
24. C. J. Tokar, P. B. Kettler, W. B. Tolman, Organometallics 1992, 11, 2737-2739.
25. D. D. LeCloux, C. J. Tokar, M. Osawa, R. P. Houser, M. C. Keyes, W. B. Tolman, Organometallics 1994, 13, 2855-2866.
26. V. S. Joshi, V. K. Kale, K. M. Sathe, A. Sarker, S. S. Tavale, C. G. Suresh, Organometallics 1991, 10, 2898-2902.
27. H. Vahrenkamp, B. Müller, Eur. J. Inorg. Chem. 1999, 129-135.
28. A. Bino, D. Gibson, Inorg. Chim. Acta 1982, 65, L37-L38.
29. D. J. Darensbourg, S. J. Lewis, J. L. Rodgers, J. C. Yarbrough, Inorg. Chem. 2003, 42, 581-589.
30. P. G. Cozzi, T. Carofiglio, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1993, 12, 2845-2848.
31. L. T. Yildirim, Ü. Ergun, Acta Crystallogr., Sect. E 2007, 63, m2424-2425.
32. A. Stockhammer, K.-H. Dahmen, T. Gerfin, L. M. Venanzi, V. Gramlich, W. Petter, Helv. Chim. Acta 1991, 74, 989-992.
33. M. G. B. Drew, S. Hollis, J. Chem. Soc., Dalton Trans. 1978, 511-516.
34. E. Bermejo, A. Castiñeiras, L. M. Fostiak, I. G. Santos, J. K. Swearingen, D. X. West, Polyhedron 2004, 23, 2303-2313.
35. P. D. Knight, A. J. P. White, C. K. Williams, Inorg. Chem. 2008, 47, 11711-11719.
36. G. Borisov, S. G. Varbanov, L. M. Venanzi, A. Albinati, F. Demartin, Inorg. Chem. 1994, 33, 5430-5437.
37. X. Liu, C. A. Kilner, M. A. Halcrow, Chem. Commun. 2002, 704-705.
38. Y. Matsunaga, K. Fujisawa, N. Amir, Y. Miyashita, K.-I. Okamoto, J. Coord. Chem. 2005, 58, 1047-1061.
39. G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112-122.