70533-09-4Relevant articles and documents
REACTIONS OF PENTAFLUOROPHENYLTRIMETHYLSILANE AND CYANOMETHYLTRIMETHYLSILANE WITH CARBONYL COMPOUNDS CATALYZED BY CYANIDE ANIONS
Gostevskii, B. A.,Kruglaya, O. A.,Albanov, A. I.,Vyazankin, N. S.
, p. 157 - 166 (1980)
Treatment of pentafluorophenyltrimethylsilane (I) and cyanomethyltrimethylsilane (II) with enolizable ketones in the presence of a catalytic amount of potassium cyanide-18-crown-6 complex gave the corresponding trimethylsilyl enol ethers.The same dehydrogenative silylation of acetylacetone and benzoylacetone with silane I was extended to the preparation of 2,4-bis(trimethylsiloxy)-1,3-pentadiene and 1-phenyl-1,3-bis(trimethylsiloxy)-1,3-butadiene, respectively.The dehydrogenative silylation of acetylacetone and benzoylacetone with dimethylbis(pentafluorophenyl)silane u nder the same conditions affords novel heterocycles 5-methylene-2,6-dioxa-1-silacyclohex-3-enes.In the reaction studied the silylating ability of the silanes increases in the order Me3SiCN ca.Me2Si(CN)2 Me3SiCH2CN Me3SiC6F5 ca.Me2Si(C6F5)2.On the other hand, potassium cyanide-18-crown-6 complex catalyzed the addition of silane I or II to a carbonyl group of non-enolizable compounds such as benzaldehyde, crotonaldehyde, and methyl(triethylgermyl)ketene.
Copper-bisphosphine-initiated pentafluorophenylation of aldehydes and ketones
Brogan, Samatha,Carter, Neil B.,Lam, Hon Wai
supporting information; experimental part, p. 615 - 617 (2010/09/18)
In the presence of substoichiometric quantities of a copper-bisphosphine complex, a variety of aldehydes and reactive ketones undergo pentafluorophenylation using pentafluorophenyl-trimethylsilane. Georg Thieme Verlag Stuttgart.
