The Effect of Added Silver Nitrate on the Palladium-Catalyzed Arylation of Allyltrimethylsilanes

Journal of Organic Chemistry

Volumn 50, Issue 20, 1985, Pages 3896-3900

  Karabelas, Kostas ^a   Westerlund, Christer ^a   Hallberg, Anders ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001541185     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00220a042     Document Type: Article

References (13)

1. For reviews, see: (a) Colvin, E. W.; Silicon in Organic Synthesis; Butterworths: London, 1981. (b) Weber, W. P. “Silicon Reagents for Organic Synthesis”; Springer-Verlag: New York, 1983.
2. Chan, T. H.; Fleming, I. Synthesis 1979, 761 and references cited therein.
3. For reviews, see: (a) Heck, R. F. Org. React. (N.Y.) 1982, 27, 345. (b) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
4. (a) Useful -allylpalladium complexes are formed after attack of palladium(II) at the -position of allylsilanes: Hayashi, T.; Konishi, M.; Humada, M. J. Chem. Soc., Chem. Commun. 1983, 736. (b) For palladium-catalyzed cycloaddition of [2-(acetoxymethyl)-3-allyl]trimethylsilane with electron-deficient olefins, see: Trost, B. M.; Chan, D. T. J. Am. Chem. Soc. 1983, 105, 2326 and references therein.
5. Hallberg, A.; Westerlund, C. Chem. Lett. 1982, 1993.
6. (a) The desilylation involved in the formation of 3-(polyfluoroalkyl)-1-propenes through the Fe3(CO)12- or Ru3(CO)12-catalyzed reaction of polyfluoroalkyl halide with allylsilanes has been suggested to occur via similar intermediates: Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1984, 25, 307. (b) For cleavage of (E)-2-(phenylethenyl)trimethylsilane with palladium chloride, see: Weber, W. P.; Felix, R. A.; Willard, A. K.; Koenig, K. E.Tetrahedron Lett. 1971, 4701.
7. An example of chloride abstraction by silver triflate from an arylpalladium chloride derivative giving a binuclear complex containing Pd-H-Pd bonds has recently been reported by: Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1984, 260, C52-C54.
8. Spencer, A. J. Organomet. Chem. 1983, 258, 101.
9. Jeffrey, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
10. Selected methods for preparation of 1 and related compunds were from the following. (a) From aldehydes and [2-(trimethylsilyl)-ethylidine]triphenylphosphorane: Seyferth, D.; Wursthorn, K. R.; Lim, T. F. O.; Sepelak, D. J. J. Organomet. Chem. 1979, 181, 293. (b) From aldehydes and 1-(phenylsulfonyl)-2-(trimethylsilyl)ethane: Hsiao, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 23, 1963. (c) From propiophenone or phenylacetone and their (phenylsulfonyl)hydrazones, butyllithium, and trimethylsilyl chloride: Fristad, W. E.; Han, Y.-K.; Paquette, L. A. J. Organomet. Chem. 1979, 174, 27. (d) From allylic esters, hexamethyldisilane, and catalytic amounts of palladium(0) or rhodium(I) complex: Urata, H.; Suzuki, H.; Moro-oka, Y.; Ikawa, T. Bull. Chem. Soc. Jpn. 1984, 57, 607. (e) From bromostyrene and (trimethylsilyl)methylmagnesium chloride in the presence of nickel(II) complex: Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 24, 2865 and references cited therein. For preparation of 2, i.e., (f) from alkanesulfonyl chloride and (trimethylsilyl)diazomethane: Aoyama, T.; Toyama, S.; Tamaki, N.; Shioiri, T. Chem. Pharm. Bull. 1983, 31, 2957. For preparation of 3 and related compounds, see the following. (g) From esters and (trimethylsilyl)methylmagnesium chloride: Fleming, I.; Pearce, A. J. Chem. Soc., Perkin Trans. 1 1981, 251. (h) From silyl enol ethers and (trimethylsilyl)methylmagnesium chloride in the presence of nickel catalyst: Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915. (i) From enol phosphates and (trimethylsilyl)methylmagnesium halide in the presence of nickel or palladium catalysts: Hayashi, T.; Fujiwa, T.; Okamoto, Y.; Katsuro, Y.; Kumada, M. Synthesis 1981, 1001.
11. Dunoguès, J.; Calas, R.; Ardoin, N.; Biran, C. J. Organomet. Chem. 1971, 32, C31-C34.
12. Ziegler, C. B.; Heck, R. F. J. Org. Chem. 1978, 43, 2941.
13. Carey, F. A.; Toler, J. R. J. Org. Chem. 1976, 41, 1966.