Palladium-Catalyzed Cascade Carbometalation of Alkynes and Alkenes as an Efficient Route to Cyclic and Polycyclic Structures

Journal of the American Chemical Society

Volumn 111, Issue 9, 1989, Pages 3454-3456

  Zhang, Yantao ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008845915     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00191a066     Document Type: Article

References (13)

1. Metal-Promoted Cyclization. 25. Part 24: Negishi, E.; Iyer, S.; Rousset, C. J. Tetrahedron Lett. 1989, 30, 291. The results herein described were presented at the 196th American Chemic l Society Meeting, Los Angeles, CA, September 25-30, 1988; ORGN 264.
2. Heck, R. F. Org. React. 1982, 27, 345. (b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
3. For recent papers not cited in ref 2b, see: (a) Kasahara, A.; Izumi, T.; Murakami, S.; Ynai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, J. J. Chem. Soc., Chem. Commun. 1986, 1697. (c) Abelman,. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4133. (d) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291. (e) Burns, B.; Grigg, R.; Ratananukul, P.; Sridharan, V.; Stevenson, P.; Worakun, T. Tetrahedron Lett. 1988, 29, 4329. (f) Negishi, E.; Nguyen, T.; O'Connor, B.; Evans, J. M.; Silveira, A., Jr. Heterocycles 1989, 0000.
4. Narula, C. K.; Mak, K. T.; Heck, R. F. J. Org. Chem. 1983, 48, 2792. (b) Grigg, R.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1984, 1073; Tetrahedron 1988, 44, 2033. (c) Tour, J. M.; Negishi, E. J. Am. Chem. Soc. 1985, 107, 8289. (d) Negishi, E.; Zhang, Y.; O'Connor, B. Tetrahedron Lett. 1988, 29, 2915. (e) Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919. (f) O'Connor, B.; Zhang, Y.; Negishi, E.; Luo, F. T.; Chen, J. W. Tetrahedron Lett. 1988, 29, 3903. (g) Zhang, Y.; O'Connor, B.; Negishi, E. J. Org. Chem. 1988, 53, 5588.
5. Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 2.
6. For arene-forming reactions similar to those described in ref 5 that are mostly stoichiometric in Pd, see: Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238 and earlier references cited therein.
7. For catalytic carbopalladation of alkynes followed by hydrogenolysis, see: (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron 1985, 41, 5121. (b) Burns, B.; Grigg, R.; Sridharan, V.; Worakun, T. Tetrahedron Lett. 1988, 29, 4325.
8. After completion of this study, a paper describing a cascade carbopalladation involving enynes in a different context was published [Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 10, 7255].
9. Tour, J. M.; Negishi, E. J. Am. Chem. Soc. 1985, 107, 8289.
10. Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328.
11. For a review, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon—Carbon Bonds; Pergamon Press: Oxford, 1986.
12. Ayanoglu, E.; Gebreyesus, T.; Beechan, L. M.; Djerassi, C.; Kaisin, M. Tetrahedron Lett. 1978, 1671. For a recent review on the synthesis of capnellene, see: Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: New York, 1987.
13. Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863.