54813-58-0Relevant academic research and scientific papers
Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents
Das, Manas,O'Shea, Donal F.
, p. 6448 - 6460 (2013/07/26)
The regioselective benzylic metalation of toluenes using BuLi/KO tBu/TMP(H) (LiNK metalation conditions) and subsequent transmetalation to Si by reaction with TMSCl provides a general one-pot procedure for the synthesis of substituted benzyltrimethylsilanes. ArCH 2Si(Me)3 derivatives are bench stable reagents yet can serve as benzyl anion equivalents under mild reaction conditions. Following activation with fluoride they can successfully participate in a wide range of additions to both non-enolizable and enolizable carbonyls. In addition, their use in the synthesis of isochromanones and trifluoromethylated amines is illustrated. The broad synthetic scope and mild practical conditions of use for ArCH2Si(Me)3 reagents demonstrate their general potential as benzyl anion equivalents.
Three-component synthesis of α-branched amines under barbier-like conditions
Le Gall, Erwan,Haurena, Caroline,Sengmany, Stephane,Martens, Thierry,Troupel, Michel
scheme or table, p. 7971 - 7973 (2010/02/28)
(Chemical Equation Presented) An array of α-branched amines has been prepared by using an expedient three-component Mannich-type reaction among organic halides, aldehyde derivatives, and amines. The experimental procedure, which is characterized by its simplicity, employs zinc dust for the in situ generation of organozinc reagents. We show that this Barbier-like protocol constitutes a useful entry to diarylmethylamines, 1,2-diarylethylamines, α- or β-amino esters, benzylamines, and β-arylethylamines.
1,2-Diarylethanols by alternative regioselective reductive ring-opening of 2,3-diaryloxiranes
Blasio, Nadia Di,Lopardo, Maria Teresa,Lupattelli, Paolo
experimental part, p. 938 - 944 (2009/07/19)
Non-symmetrical ￡rans-2,3-diaryloxiranes have been regioselectively opened by catalytic hydrogenation over Pd/C, NaBH4/Pd and [Cp 2TiCl]/H2O. Although in the catalytic hydrogenation reactions the epoxides were mainly opened at the β-carbon with respect to the substituted aryl ring in all cases, with the [Cp2TiCl]/H 2O system the regioselectivity was affected by the electronic properties of the aryl residues, the epoxides being opened on the carbon bearing the most electron-releasing or the least electron-withdrawing group. With the NaBH4/Pd system different regioisomers were obtained depending on the substituents. Starting from enantioenriched epoxides, no loss of optical purity was observed in the alcohols formed.
Catalytic reduction of an α,β-disubstituted alkene with sodium borohydride in the presence of tetra-tert-butylphthalocyanine complexes
Kalashnikov, Valery V.,Tomilova, Larisa G.
, p. 343 - 344 (2008/04/05)
Cobalt tetra-tert-butylphthalocyanine was found an efficient catalyst for the catalytic reduction of 4-[(E)-2-phenylethenyl]-pyridine to 4-(2-phenylethyl)pyridine with sodium borohydride.
