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)
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.