Acetylene-substituted phosphane oxides: Building blocks for macrocycles

European Journal of Organic Chemistry

Volumn , Issue 15, 2007, Pages 2405-2412

  Van Assema, Sander G A ^a   De Jong, G Bas ^a   Ehlers, Andreas W ^a   De Kanter, Frans J J ^a   Schakel, Marius ^a   Spek, Anthony L ^b   Lutz, Martin ^b   Lammertsma, Koop ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Alkynes; Cross coupling; Macrocycles; Phosphanes; Phosphorus heterocycles

Indexed keywords

EID: 34250645881     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600877     Document Type: Article

References (49)

1. a) N. N. P. Moonen, R. Gist, C. Boudon, J.-P. Gisselbrecht, P. Seiler, T. Kawai, A. Kishioka, M. Gross, M. Irie, F. Diederich, Org. Biomol. Chem. 2003, 1, 2032-2034;
2. b) T. Michinobu, J. C. May, J. H. Lim, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, I. Biaggio, F. Diederich, Chem. Commun. 2005, 737-739;
3. c) N. N. P. Moonen, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, F. Diederich, Angew. Chem. Int. Ed. 2002, 41, 3044-3047.
4. a) R. E. Martin, F. Diederich, Angew. Chem. Int. Ed. 1999, 38, 1350-1377;
5. Angew. Chem. 1999, 111, 1440-1469;
6. b) F. Diederich, L. Gobbi, Top. Curr. Chem. 1999, 201, 43-79;
7. c) M. B. Nielsen, F. Diederich, Synlett 2002, 544-552.
8. K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy, Wiley, Chichester, 1998.
9. a) M. Hissler, P. W. Dyer, R. Réau, Top. Curr. Chem. 2005, 250, 127-163;
10. b) M. Hissler, C. Lescop, R. Réau, J. Organomet. Chem. 2005, 690, 2482-2487;
11. c) C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulászi, R. Réau, Chem. Eur. J. 2001, 7, 4222-4236.
12. a) L. T. Scott, M. Unno, J. Am. Chem. Soc. 1990, 112, 7823-7825;
13. b) L. T. Scott, M. J. M. Cooney, Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995, ch. 9, pp. 321-351.
14. G. Märkl, T. Zollitsch, P. Kreitmeier, M. Prinzhorn, S. Reithinger, E. Eibler, Chem. Eur. J. 2000, 6, 3806-3820.
15. a) R. J. P. Corriu, C. Guérin, B. J. L. Henner, A. Jolivet, J. Organomet. Chem. 1997, 530, 39-48;
16. b) Y.-C. Chang, J.-C. Lee, F.-E. Hong, Organometallics 2005, 24, 5686-5695;
17. c) S. B. Bushuk, F. H. Carre, D. M. H. Guy, W. E. Douglas, Y. A. Kalvinkovskya, L. G. Klapshina, A. N. Rubinov, A. P. Stupak, B. A. Bushuk, Polyhedron 2004, 23, 2615-2623.
18. a) S. Rumthao, O. Lee, Q. Sheng, W. Fu, D. C. Mulhearn, D. Crich, A. D. Mesecar, M. E. Johnson, Bioorg. Med. Chem. Lett. 2004, 14, 5165-5170;
19. b) V. Vicente, A. Fruchier, M. Taillefer, C. Combes-Chamalet, I. J. Scowen, F. Plenat, H.-J. Cristau, New J. Chem. 2004, 28, 418-424.
20. R. B. King, N. D. Sadanani, J. Org. Chem. 1985, 50, 1719-1722.
21. K. Toyota, M. Shibata, M. Yoshifuji, Bull. Chem. Soc. Jpn. 1995, 68, 2633-2638.
22. a) T. Koizumi, P. Haake, J. Am. Chem. Soc. 1973, 95, 8073-8079;
23. b) E. I. Matrosov, E. E. Kryuchkov, E. E. Nifantyev, A. G. Kozachenko, M. I. Kabachnik, Phosphorus Sulfur 1982, 13, 69-78;
24. c) M. J. P. Harger, P. A. Shimmin, Tetrahedron 1992, 48, 7539-7550;
25. d) R. P. Polniaszek, J. Org. Chem. 1992, 57, 5189-5195.
26. A. A. Cantrill, H. M. I. Osborn, J. Sweeney, Tetrahedron 1998, 54, 2181-2208.
27. a) O. Korpiun, R. A. Lewis, J. Chickos, K. Mislow, J. Am. Chem. Soc. 1968, 90, 4842-4846;
28. b) F. Fredoueil, M. Evain, D. Massiot, M. Bujoli-Doeuff, B. Bujoli, J. Mater. Chem. 2001, 11, 1106-1110;
29. c) M. Finke, H.-J. Kleiner, Justus Liebigs Ann. Chem. 1974, 741-750.
30. A.-M. Caminade, F. El Khatib, A. Baceiredo, M. Koenig, Phosphorus Sulfur 1987, 29, 365-367.
31. The mono-TMS adduct was prepared by following the same procedure but by using TMSCl. However, desilylation was observed upon purification by column chromatography on silica gel.
32. a) R. M. Acheson, P. J. Ansell, J. R. Murray, J. Chem. Res. (M) 1986, 3001;
33. R. M. Acheson, P. J. Ansell, J. R. Murray, J. Chem. Res. (S) 1986, 378;
34. b) S. G. Dutremez, C. Guerin, B. J. L. Henner, V. Tomberli, Phosphorus Sulfur Silicon Relat. Elem. 2000, 160, 251-269.
35. a) C. Glaser, Ber. Dtsch. Chem. Ges. 1869, 2, 422-424;
36. b) C. Glaser, Justus Liebigs Ann. Chem. 1870, 154, 137-171.
37. a) G. Eglinton, A. R. Galbraith, Chem. Ind. (London) 1956, 737-738;
38. b) O. M. Behr, G. Eglinton, A. R. Galbraith, R. A. Raphael, J. Chem. Soc. 1960, 3614-3625.
39. a) A. S. Hay, J. Org. Chem. 1960, 25, 1275-1276;
40. b) A. S. Hay, J. Org. Chem. 1962, 27, 3320-3321.
41. E. Valenti, M. A. Pericàs, F. Serratosa, J. Am. Chem. Soc. 1990, 112, 7405-7406.
42. For a description of whiskers, see also: P. van der Sluis, Ph. D. Thesis, Utrecht University, 1989, ch. 4, pp. 31-48.
43. M. L. G. Borst, R. E. Bulo, C. W. Winkel, D. J. Gibney, A. W. Ehlers, M. Schakel, M. Lutz, A. L. Spek, K. Lammertsma, J. Am. Chem. Soc. 2005, 127, 5800-5801.
44. H. Zhang, K. T. Lam, Y. L. Chen, T. Mo, C. C. Kwok, W. Y. Wong, M. S. Wong, A. W. M. Lee, Tetrahedron Lett. 2002, 43, 2079-2082.
45. L. Brandsma, Preparative Acetylenic Chemistry, 2nd ed., Elsevier, New York, 1988.
46. G. M. Sheldrick, SADABS: Area-Detector Absorption Correction, v2.10, Universität Göttingen, Germany, 1999.
47. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
48. G. M. Sheldrick, SHELXL-97: Program for crystal structure refinement, University of Göttingen, Germany, 1997.
49. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.