20445-36-7Relevant academic research and scientific papers
Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and imines with (perfluoroalkyl)trimethylsilane
Kawano, Yoshikazu,Kaneko, Nobuya,Mukaiyama, Teruaki
, p. 1133 - 1145 (2007/10/03)
Lewis base-catalyzed perfluoroalkylation of carbonyl compounds and aldimines with (perfluoroalkyl)trimethylsilanes (TMSCF3, TMSC 2F5, and TMSC3F7) is described. The nitrogen- or oxygen-containing anions generated from amides, imides, and carboxylic acids have been found to work as effective Lewis-base catalysts in perfluoroalkylation that proceeds via activation of the carbon-silicon bonds of (perfluoroalkyl)trimethylsilanes. Reactions of carbonyl compounds such as aldehydes, ketones, and esters with TMSCF3 in the presence of a catalytic amount of Lewis bases proceeded smoothly to afford the corresponding adducts in good-to-high yields under mild conditions. Although it was considered difficult, this catalytic perfluoroalkylation of various aldimines with (perfluoroalkyl)trimethylsilane in the presence of Lewis bases such as lithium acetate or benzoate proceeded efficiently to give the corresponding perfluoroalkylated adducts, because the aldimines here were weak electrophiles toward (perfluoroalkyl)trimethylsilanes. The present reaction is, therefore, the first example of a catalytic perfluoroalkylation of aldimines.
Some studies on nucleophilic trifluoromethylation using the shelf-stable trifluoromethylacetophenone-N,N-dimethyltrimethylsilylamine adduct
Motherwell, William B.,Storey, Lynda J.
, p. 491 - 498 (2007/10/03)
The simple thermal addition product of N,N-dimethyltrimethylsilylamine with 2,2,2-trifluoroacetophenone provides a shelf-stable reagent for nucleophilic trifluoromethylation of both the carbonyl and the imine group.
The trifluoromethylacetophenone-N,N-dimethyltrimethylsilylamine adduct - A new shelf stable reagent for nucleophilic trifluoromethylation
Motherwell, William B.,Storey, Lynda J.
, p. 646 - 648 (2007/10/03)
The simple thermal addition product of N,N-dimethyltrimethylsilylamine with trifluoromethylacetophenone provides a shelf-stable reagent for nucleophilic trifluoromethylation of the carbonyl group.
ELECTROCHEMICAL TRIFLUOROMETHYLATION OF CARBONYL COMPOUNDS
Sibille, S.,Mcharek, S.,Perichon, J.
, p. 1423 - 1428 (2007/10/02)
The electroreduction of CF3Br in DMF containing aldehydes or ketones, using a sacrificial zinc anode, affords the corresponding trifluoromethyl alcohols together with the unreactive organozinc species CF3ZnBr and (CF3)2Zn.The alcohols are obtained with good yields from aldehydes.With ketones the organozinc species are formed preferentially to the alcohols, but the addition of tetramethylene-diamine allows the alcohols to form with moderate yields.
α-TRIFLUOROMETHYL-α-HYDROXY CARBOXYLIC ACIDS
Soloshonok, V. A.,Gerus, I. I.,Yagupol'skii, Yu. L.,Kukhar', V. P.
, p. 1298 - 1303 (2007/10/02)
The methyl esters of α-trifluoromethyl-α-hydroxy carboxylic acids were obtained by the reaction of methyl trifluoropyruvate with organometallic reagents (Cd, Mg, Zn).The characteristic features of the reactions in relation to the nature of the alkylating agent were demonstrated.
