Selective Activation of Alkyl- and Aryl-Oxygen Single Bonds in Solution with Transition Metal Complexes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 625-626

  Van Der Boom, Milko E ^a   Liou, Shyh Yeon ^a   Ben David, Yehoshoa ^a   Vigalok, Arkadi ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

C O activation; Homogeneous catalysis; Insertions; Palladium; Rhodium

Indexed keywords

EID: 0030892024     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706251     Document Type: Article

References (31)

1. a) E. Furimsky, Catal. Rev. Sci. Eng. 1983, 25, 421;
2. b) J. H. Gary, G. E. Handwerk, Petroleum Refining: Technology and Economics, 3rd Ed., Marcel Dekker, New York, 1993;
3. c) J. G. Speight, The Chemistry and Technology of Petroleum, Marcel Dekker, New York, 1983;
4. d) T. E. Caldwell, I. M. Abdelrehim, D. P. Land, J. Am. Chem. Soc. 1996, 118, 907.
5. a) D. B. Grotjahn, C. Joubran, Organometallics 1995, 14, 5171;
6. b) A. Yamamoto, Adv. Organomet. Chem. 1992, 34, 111 and references therein;
7. c) T. Yamamoto, O. Saito, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 5600;
8. d) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, A. Yamamoto, ibid. 1980, 102, 3758;
9. e) D. B. Grotjahn, H. C. Lo, Organometallics 1996, 15, 2860.
10. a) C. E. Jones, B. E. Shaw, B. E. Turtle, J. Chem. Soc. Dalton Trans. 1974, 992;
11. b) H. D. Empsall, E. M. Hyde, C. E. Jones, B. L. Shaw, ibid. 1974, 1980;
12. c) S. D. Ittel, C. A. Tolman, A. D. English, J. P. Jesson, J. Am. Chem. Soc. 1978, 100, 7577;
13. d) C. A. Tolman, S. D. Ittel, A. D. English, J. P. Jesson, ibid. 1979, 101, 1742;
14. e) K. R. Dunbar, S. C. Haefner, C. E. Uzelmeizer, A. Howard, Inorg. Chim. Acta 1995, 240, 527.
15. a) J. B. Bonanno, T. P. Henry, D. R. Neithamer, P. T. Wolczanski, E. B. Lobkovsky, J. Am. Chem. Soc. 1996, 118, 5132;
16. b) M. Gozin, A. Weisman, Y. Ben-David, D. Milstein, Nature 1993, 364, 699;
17. c) M. Gozin, M. Aizenberg, S.-Y. Liou, A. Weisman, Y. Ben-David, D. Milstein, ibid. 1994, 370., 42;
18. d) S.-Y. Liou, M. Gozin, D. Milstein, J. Am. Chem. Soc. 1995, 117, 9774;
19. e) S.-Y. Liou, M. Gozin, D. Milstein, J. Chem. Soc. Chem. Commun. 1995, 1965;
20. f) M. E. van der Boom, H.-B. Kraatz, Y. Ben-David, D. Milstein, Chem. Commun. 1996, 2167.
21. 1H} NMR spectroscopy.
22. a) C. J. Moulton, B. L. Shaw, J. Chem. Soc. Dalton Trans. 1976, 1020;
23. b) S. Nemeh, C. Jensen, E. Binamira-Soriaga, W. C. Kaska, Organometallics 1983, 2, 1442.
24. a) A. Gordon, A. Ford, The Chemist's Companion, Wiley, New York, 1972;
25. b) Handbook of Chemistry and Physics, 57th Ed., CRC Press, Boca Raton, 1976-1977.
26. +), correct isotope pattern. Details of the synthesis will be published elsewhere.
27. It is not clear at this stage if the initial Ar-O oxidative addition is also the thermodynamically favored process.
28. +), correct isotope pattern.
29. Recently, two analogous benzylic and phenoxy palladium(II) complexes were fully characterized by NMR spectroscopy and X-ray diffraction; the triflate anion is end-on coordinated to the metal center. M. E. van der Boom, L. J. W. Shimon, Y. Ben-David, D. Milstein, unpublished results.
30. Shaw et al. reported the formation of the chloride analog of 5 [6].
31. M. V. Bhatt, S. U. Kulkarni, Synthesis 1983, 249.