Elaboration of Conjugated Alkenes Initiated by Insertion into a Vinylic C-H Bond

Journal of the American Chemical Society

Volumn 117, Issue 19, 1995, Pages 5371-5372

  Trost, Barry M ^a   Imi, Katsuharu ^a   Davies, Ian W ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000797948     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00124a025     Document Type: Article

References (13)

1. Trost, B. M. Science 1991 254, 1471; Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
2. Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Vol. 4, Chapter 1.1, pp 1—68. Lee, V. J. Idem.; Chapter 1.2, pp 69—138; Chapter 1.3, pp 139–168. Kozlowski, J. A. Idem.; Chapter 1.4, pp 169—198. Schmalz, H. G. Idem.; Chapter 1.5, pp 199—236. Hulce, M.; Chapdelaine, M. J. Idem.; Chapter 1.6, pp 237–268.
3. Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Vol. 3, Chapter 1.1, pp 21—25, 50–53.
4. Cyclometalation of substituted aromatics is well documented; see: Newcome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. Ryabov, A. D. Chem. Rev. 1990, 90, 403. Dunina, V. V.; Zalevskaya, D. A.; Potapov, V. M. Russ. Chem. Rev. 1990, 90, 403. For a recent reference, see: Valk, J.-M.; Maassarani, F.; van der Slius, P.; Spek, A. L.; Boersma, J.; van Koten, G. Organometallics 1994, 13, 2320. For catalytic reactions involving initiation by such a process with Ru complexes, see: Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728. Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778. Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888. Murai, S.; Kakiuchi, F.; Sekimo, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
5. Net addition of a vinylic C-H bond across a double bond not involving a metal-catalyzed C—H insertion as the initiation step is known. Misono, A.; Uchida, Y.; Hidai, M.; Inomata, I. J. Chem. Soc. D 1968, 704. Bogdanovic, B.; Henc, B.; Meister, B.; Pauling, H.; Wilke, G. Angew. Chem., Int. Ed. Engl. 1972, 84, 1070. Nugent, W. A.; Hobbs, F. W. J. Org. Chem. 1983, 43, 5364. Nugent, W. A.; McKinney, R. J. J. Mol. Catal. 1985, 29, 65. Buono, G.; Siv, C.; Peiffer, G.; Triantaphylides, C.; Denis, P.; Mortreux, A.; Petit, F. J. Org. Chem. 1985, 50, 1781. McKinney, R. J.; Colton, M. C. Organometallics 1986, 5, 1080. Brookhart, M.; Sabo-Etienne, S. J. Am. Chem. Soc. 1991, 113, 2777. Kovalev, I. P.; Strelenko, Y. A.; Ignatenko, A. V.; Vinogradov, M. G.; Nikishin, G. I. J. Organomet. Chem. 1991, 420, 125. Ohgomori, Y.; Ichikawa, S.; Sumitani, N. Organometallics 1994, 13, 3758.
6. For oxidative addition of a ruthenium complex into a vinylic C—H bond, see: Komiya, S.; Yamamoto, A. Chem. Lett. 1975, 475. Komiya, S.; Ito, T.; Cowie, M.; Yamamoto, A.; Ibers, J. A. J. Am. Chem. Soc. 1976, 98, 3874.
7. Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37. Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694.
8. Albers, M. O.; Robinson, D. J.; Shaver, A.; Singleton, E. Organometallics 1986, 5, 2199. For a review, see: Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
9. leBozec, H.; Touchard, D.; Dixneuf, P. H. Adv. Organomet. Chem. 1989, 29, 163.
10. Allen, D. W.; Hutley, B. G.; Mellor, M. T. J. Chem. Soc., Perkin Trans. 1, 1972, 63. Farina, V.; Baker, S. R.; Benigni, D. A.; Sapino, C., Jr. Tetrahedron Lett. 1988, 29, 5739.
11. For a leading reference, see: Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S.; Naota, T. Chemtracts: Org. Chem. 1994, 7, 281.
12. 6 complexes with one of the phenyl rings. Cf.: McConway, C.; Skapski, A. C.; Phillips, L.; Young, R. J.; Wilkinson, G. J. Chem. Soc., Chem. Commun. 1974, 327. However, such a species would not be expected to be catalytically active in these reactions.
13. This observation combined with the position of the double bond in the product suggests that a metallacycle intermediate involving the two alkene reactants that could be envisioned as an intermediate is unlikely. Metallacycles between alkenes and alkynes are known with this catalyst; see: Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Am. Chem. Soc. 1994, 116, 3645.