Convergence of mechanistic pathways in the palladium(0)-catalyzed cross-coupling of alkenylsilacyclobutanes and alkenylsilanols

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2491-2494

  Denmark, Scott E ^a   Wehrli, Daniel ^a   Choi, Jun Young ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000198109     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006170y     Document Type: Article

References (13)

1. (a) Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
2. (b) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
3. (c) Tsuji, I. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995.
4. (a) Denmark, S. E.; Choi, J.-Y. J. Am. Chem. Soc. 1999, 121, 5821.
5. (b) Denmark, S. E.; Wu, Z. Org. Lett. 1999, 1, 1495.
6. (c) Denmark, S. E.; Wang, Z. Synthesis 2000, 999.
7. (a) Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565.
8. (b) For previous studies on silicon-based cross-coupling reactions see: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10.
9. Commercial TBAF is a crystalline trihydrate. Despite many reports on the dehydration of TBAF, this process primarily results in the formation of bifluoride. Albanese, D.; Landini, D.; Penso, M. J. Org. Chem. 1998, 63, 9587.
10. We surmise that this is due to the accumulation of a silicon-containing byproduct which scavenges some of the fluoride activator.
11. The typical chemical shift range for tetracoordinate silicon is δ 30 to -30 ppm, for pentacoordinate silicon is δ -75 to -130 ppm. Takeuchi, Y.; Takayama, T. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley: Chichester, 1998; Chapter 6, Vol. 2, Part 1.
12. 29Si NMR, -13.9 and -15.2 ppm, neither of which corresponded to 14.
13. Christe, K. O.; Wilson, W. W.; Wilson, R. D.; Bau, R. Feng, J. J. Am. Chem. Soc. 1990, 112, 7619.