71268-59-2Relevant articles and documents
Halogenative difluorohomologation of ketones
Fedorov, Oleg V.,Kosobokov, Mikhail D.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 5870 - 5876 (2015/06/16)
A method for the difluorohomologation of ketones accompanied by halogenation of a C-H bond is described. The reaction involves silylation, difluorocarbene addition using Me3SiCF2Br activated by a bromide ion, and halogenation of intermediate cyclopropanes with N-bromo- or N-iodosuccinimide. The whole process is performed without isolation of intermediates. The resulting α,α-difluoro-β-halo-substituted ketones can be readily converted into fluorine containing pyrazole derivatives and oxetanes.
Reaction of acylsilanes with α-sulfinyl carbanions: Regioselective synthesis of silyl enol ethers
Honda, Mitsunori,Nakajima, Tadashi,Okada, Maiko,Yamaguchi, Keita,Suda, Mitsuhiro,Kunimoto, Ko-Ki,Segi, Masahito
experimental part, p. 3740 - 3742 (2011/08/06)
The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding unsymmetrical ketones with base.
In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers
Kerr, William J.,Watson, Allan J. B.,Hayes, Douglas
experimental part, p. 1238 - 1243 (2008/10/09)
Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes2Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process. The Royal Society of Chemistry.
