Selective homo- and heterodehydrocouplings of phosphines catalyzed by rhodium phosphido complexes

Journal of the American Chemical Society

Volumn 128, Issue 42, 2006, Pages 13698-13699

  Han, Li Biao ^a   Tilley, T Don ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE; RHODIUM; RHODIUM PHOSPHIDO COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIASTEREOISOMER; DIMERIZATION; HEATING; HETERODEHYDROCOUPLING; HOMODEHYDROCOUPLING; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY; X RAY CRYSTALLOGRAPHY;

CATALYSIS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; RHODIUM; STEREOISOMERISM;

EID: 33750369278     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065346+     Document Type: Article

References (39)

1. (a) Hirao, T.; Masaunaga, T.; Yamada, N.; Oshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
2. (b) Herd, O.; Hessler, A.; Hingst, M.; Tepper, M.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
3. (c) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
4. (d) Hirai, T.; Han, L.-B. J. Am. Chem. Soc. 2006, 128, 7422.
5. (e) Levine, A. M.; Stockland, R. A., Jr.; Clark, R.; Guzei, I. Orgatanometallics 2002, 21, 3278.
6. (f) Deprèle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386.
7. (g) Moncarz, J. R.; Laritcheva, N. F.; Glueck, D. S. J. Am. Chem. Soc. 2002, 124, 13356.
8. (h) Shulyupin, M. O.; Kazakova, M. A.; Beletskaya, I. P. Org. Lett. 2002, 4, 761.
9. Gauvin, F.; Harrod, J. F.; Woo, H. G. Adv. Organomet. Chem. 1998, 42, 363.
10. 2 with Ti and Zr: (a) Fermin, M. C.; Stephan, D. W. J. Am. Chem. Soc. 1995, 117, 12645.
11. (b) Stephan, D. W. Angew. Chem., Int. Ed. 2000, 39, 314.
12. (c) Xin, S.; Woo, H. G.; Harrod, J. F.; Samuel, F.; Lebuis A.-M. J. Am. Chem. Soc. 1997, 119, 5307 .
13. 2, 3% yield at 145 °C after 18 h).
14. 3: Shu, R.; Hao, L.; Harrod, J. F.; Woo, H.-G.; Samuel, E. J. Am. Chem. Soc. 1998, 120, 12988.
15. 3: Dorn, H.; Singh, R. A.; Massey, J. A.; Nelson, J. M.; Jaska, C. A.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2000, 122, 6669.
16. (c) Dehydrocouplings of phosphine-borane adducts: McWilliams, A. R.; Dorn, H.; Manners, I. Top. Curr. Chem. 2002, 120, 141.
17. (a) Fryzuk, M. D.; McConville, D. H.; Rettig, S. J. J. Organomet. Chem. 1993, 445, 245.
18. (b) Rosenberg, L.; Fryzuk, M. D.; Rettig, S. J. Organometallics 1999, 18, 958.
19. (c) Fryzuk, M. D.; Rosenberg, L.; Rettig, S. J. Organometallics 1996, 15, 2871.
20. (d) Fryzuk, M. D.; Clentsmith, G. K. B.; Rettig, S. J.; Haegele, G. Organometallics 1996, 15, 2083.
21. Fryzuk, M. D.; Rosenberg, L.; Rettig, S. J. Inorg. Chim. Acta 1994, 222, 345.
22. (f) Fryzuk, M. D.; Rosenberg, L.; Rettig, S. J. Organometallics 1991, 10, 2537.
23. (g) Fryzuk, M. D.; Piers, W. E.; Einstein, F. W. B.; Jones, T. Can. J. Chem. 1989, 67, 883.
24. (h) Fryzuk, M. D.; Jang, M. L.; Jones, T.; Einstein, F. W. B. Can. J. Chem. 1986, 64, 174.
25. Stradiotto, M.; Fujdala, K. L.; Tilley, T. D. Helv. Chim. Acta 2001, 84, 2958.
26. An attempted isolation of 2 was not successful owing to its ready decomposition to 3a.
27. Related phosphido-bridged complexes have been prepared by other methods. (a) Kreter, P.; Meek, D. W. Inorg. Chem. 1983, 22, 319.
28. (b) Fultz, W.; Rheingold, A. L.; Kreter, P. E.; Meek, D. W. Inorg. Chem. 1983, 22, 860.
29. (c) Burkhardt, E. W.; Mercer, W. C.; Geoffroy, G. L. Inorg. Chem. 1984, 23, 1779.
30. (d) Jones, R. A.; Norman, N. C.; Seeberger, M. H. Organometallics 1983, 2, 1629.
31. (e) Arif, A. M.; Jones, R. A.; Heaton, D. E.; Nunn, C. M.; Schwab, S. T. Inorg. Chem. 1988, 27, 254.
32. We thank B. V. Mork for performing this X-ray analysis (unpublished).
33. 2-PH at room temperature.
34. 2PH.
35. The generated catalyst in situ showed higher catalytic activity than 3a-c, but activity similar to that of 4.
36. 31P NMR data with those reported (ref 3c). When the reaction was carried out at higher temperatures, further reaction of PhHPPHPh look place to give a complicated mixture (see Supporting Information for details).
37. 2 can replace dippe from complex 3a. Once dippe is replaced the catalyst loses its activity. The addition of excess dippe presumably delays this deactivation process.
38. For a related rhodium-catalyzed dehydrocoupling of silanes with thiols, see Baruah, J. B.; Osakada, K.; Yamamoto, T. Organometallics 1996, 15, 456.
39. Complex 6 was separately generated via reaction of 1 with PhSH (see Supporting Information).