Facile Oxidative Addition of Rhodium(I) to the Acyl-Oxygen Bond of 2-((Diphenylphosphino)methyl)quinolin-8-ol Acetate

Organometallics

Volumn 14, Issue 11, 1995, Pages 5171-5177

  Grotjahn, Douglas B ^a   Joubran, Camil ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003648912     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00011a039     Document Type: Article

References (31)

1. Review: Yamamoto, A. Adv. Organomet. Chem. 1992, 34, 111-147.
2. Harrington, P. J. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12. (b) Oppolzer, W. In ref 2a.
3. Yamamoto, T.; Ishizu, J.; Kohara, T.; Komiya, S.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102, 3758–3764.
4. Zlota, A. A.; Frolow, F.; Milstein, D. Organometallics 1990, 9, 1300–1302. Aye, K.-T.; Colpitts, D.; Ferguson, G.; Puddhepatt, R. J. Organometallics 1988, 7, 1454—1456.
5. Castaño, A.; Echavarren, A. M. Tetrahedron Lett. 1990, 31, 4783–4786. Castaño, A.; Echavarren, A. M. Tetrahedron Lett. 1993, 34, 4361–4362.
6. Reviews: Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508–524. Mitchell, T. N. Synthesis 1992, 803–815. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; especially pp 363–365, 773–775.
7. Ho, T.-L. Tetrahedron 1985, 41, 1–86.
8. Phillips, J. P. Chem. Rev. 1956, 56, 271–297. Irving, H. M. N. H. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, U.K., 1987; Vol. 1, pp 521–563.
9. Yoneda, Y.; Hakushi, T.; Newkome, G.; Fronczek, F. R. Organometallics 1994, 13, 4912–4918.
10. Koh, J. J.; Lee, W.-H.; Williard, P. G.; Risen, W. M., Jr. J. Organomet. Chem. 1985, 284, 409–419. (b) Suggs, J. W. J. Am. Chem. Soc. 1978, 100, 640–641. (c) Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1984, 106, 3054–3056. Suggs, J. W.; Wovkulich, M. J.; Williard, P. G.; Lee, K. S. J. Organomet. Chem. 1987, 307, 71–82.,
11. Selected examples are as follows, (a) Chelate-driven additions of Rh(I) and Ir(I) to aldehydes: Reference 10b. Landvatter, E. F.; Rauchfuss, T. B. Organometallics 1982, 1, 506–513. (b) Cleavage of ketone C-C bonds directed by quinoline N: Reference 10c. (c) Chelate-driven oxidative additions to N-H bonds: Hedden, D.; Roundhill, D. M.; Fultz, W. C.; Rheingold, A. L. J. Am. Chem. Soc. 1984, 106, 5014–5016. Hedden, D.; Roundhill, D. M. Inorg. Chem. 1986, 25, 9–15. (d) Other additions to N-H bonds: Merola, J. S.; Ladipo, F. T. Inorg. Chem. 1990, 29, 4172–4173. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738–6744. (e) Additions to O-H bonds: Ladipo, F. T.; Kooti, M.; Merola, J. Inorg. Chem. 1993, 32, 1681–1688. Milstein, D.; Calabrese, J. C.; Williams, I. D. J. Am. Chem. Soc. 1986, 108, 6387–6389. (f) Additions to aldehydes: Milstein, D. Acc. Chem. Res. 1984, 17, 221–226. Milstein, D.; Fultz, W. C.; Calabrese, J. C. J. Am. Chem. Soc. 1986, 108, 1336–1338. (g) Additions to C-H bonds: Bergman, R. G. J. Organomet. Chem. 1990, 400, 273–282. Jones, W. D.; Feher, F. J. Acc. Chem. Res. 1989, 22, 91–100.
12. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163–1188. Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1–40.
13. Hubbard, J. L.; McVicar, W. K. Inorg. Chem. 1992, 31, 910–913. Poulton, J. T.; Sigalas, M. P.; Folting, K.; Streib, W. E.; Eisenstein, O.; Caulton, K. G. Inorg. Chem. 1994, 33, 1476–1485. Bickford, C. C.; Johnson, T. J.; Davidson, E. R.; Caulton, K. G. Inorg. Chem. 1994, 33, 1080–1086. Lunder, D. M.; Lobkovsky, E. B.; Streib, W. E.; Caulton, K. G. J. Am. Chem. Soc. 1991, 113, 1837–1838.
14. Blum, O.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 4582–4594 and references therein. Goldman, A. S.; Halpern, J. J. Organomet. Chem. 1990, 382, 237–253.
15. Brandsma, L. Preparative Polar Organometallic Chemistry; Springer: Berlin, 1990; especially p 130.
16. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190–6191.
17. Verstuyft, A. W.; Redfield, D. A.; Cary, L. W.; Nelson, J. H. Inorg. Chem. 1977, 16, 2776–2786.
18. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569–583.
19. Brown, T. H.; Green, P. J. J. Am. Chem. Soc. 1970, 92, 2359–2362.
20. Lindner, E.; Wang, Q.; Mayer, H. A.; Fawzi, R.; Steimann, M. Organometallics 1993, 12, 1865–1870.
21. Grotjahn, D. B.; Lo, H. C.; Groy, T. L. Acta Crystallogr., Sect. C, in press.
22. 13C NMR Data for Organometallic Complexes; Academic: London, 1981. See also: Mann, B. E. In Transition Metal Nuclear Magnetic Resonance; Pregosin, P. S., Ed.; Elsevier: Amsterdam, 1991; p 208.
23. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th ed.; Wiley: New York, 1986. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335–422. Kubota, M.; Blake, D. M. J. Am. Chem. Soc. 1971, 93, 1368–1373.
24. Deeming, A. J.; Shaw, B. L. J. Chem. Soc. A 1969, 1128-1134.
25. Ohkaku, N.; Nakamoto, K. Inorg. Chem. 1971, 10, 798–805.
26. Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analyses; VCH: New York, 1989; Chapter 7.
27. Ernst, R. R.; Bodenhausen, G.; Wokaun, A. Principles of Nuclear Magnetic Resonance in One and Two Dimensions; Oxford University Press: New York, 1987.
28. Juranic, N.; Likic, V.; Kostic, N. M.; Macura, S. Inorg. Chem. 1995, 34, 938–944. Giovanetti, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040–4057.
29. Deeming, A. J.; Rothwell, I. P.; Hursthouse, M. B.; Malik, K. M. A. J. Chem. Soc., Dalton Trans. 1980, 1974—1982.
30. Transition Metal Hydrides; Muetterties, E. L., Ed.; Marcel Dekker: New York, 1971.
31. van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1973, 14, 92–95.