Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran
A straightforward chemoselective protection of anilines as N-TBS derivatives is described by using a suitable deprotonation of the amine with methyllithium in the environmentally friendly and safer substitute of THF, 2-methyltetrahydrofuran, under exceptional mild reaction conditions (0 °C, 30 min). Interestingly, the protecting group maybe cleaved efficiently by simple treatment of N-TBS-anilines with silica gel in ethanol-water.
Pace, Vittorio,Alcantara, Andres R.,Holzer, Wolfgang
supporting information; experimental part
p. 1986 - 1989
(2011/09/16)
Anilinosilanes/TBAF catalyst: Mild and powerful agent for the silylation of sterically hindered alcohols
We developed an efficient method for the silylation of alcohols using anilinosilane with tetrabutylammonium fluoride (TBAF) catalyst, wherein TMS, TES and TBS groups were smoothly introduced into silylation-resistant hindered alcohols under mild condition
Novel Syntheses of Bis(trialkylsilyl)amines by Reductive Trialkylsilylation of Azo Compounds
Reduction of azo compounds with a system of a trialkylchlorosilane and lithium has been found to afford bis(trialkylsilyl)amines in the presence of a transition metal halide as a catalyst in THF.The reaction course was significantly modified by using t-butyldimethylchlorosilane as a trialkylchlorosilane.
Silylaminyl Radicals. Part 3. Electron Spin Resonance Studies of Alkyl(trialkylsilyl)aminyl Radicals
A series of N-alkyl-N-trialkylsilylaminyl radicals (R23Si=Me3Si, Et3Si, i-Pr3Si, or t-BuMe2Si) have been generated photochemically in solution and characterised using e.s.r. spectroscopy.The radicals and were also
Brand, John C.,Cook, Malcolm D.,Roberts, Brian P.
p. 1187 - 1196
(2007/10/02)
SELECTIVE N-MONOMETHYLATION OF PRIMARY AMINES via N-TRIALKYLSILYL-LITHIOAMINES
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Calverley, Martin J.
p. 601 - 610
(2007/10/02)
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