1192-95-6Relevant articles and documents
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Leonard,Musker
, p. 5631 (1959)
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Reactivity of heterocyclic α-aminomethylsilanes with alcohols
Pypowski, Krzysztof,Mojzych, Mariusz
, p. 320 - 324 (2021/03/31)
[Figure not available: see fulltext.] Alkoxylation of N-substituted heterocyclic aminomethylsilyl moieties was studied using primary and tertiary alcohols. The reaction of 4-(silylmethyl)morpholine and 1-(silylmethyl)azepane under catalyst- and solvent-free conditions leads to the formation of dialkoxy- and trialkoxyaminomethylsilyl derivatives. The methanolysis of 4-(silylmethyl)morpholine resulted in trimethoxyaminomethylsilane formation as the main product and two byproducts, i.e., tetramethoxysilane and N-methylmorpholine.
Reduction of Amides to Amines under Mild Conditions via Catalytic Hydrogenation of Amide Acetals and Imidates
Kadyrov, Renat
, p. 185 - 191 (2018/11/23)
A simple and general protocol was developed for selective conversion of amides into amines. Amides were converted into amide acetals and imido esters by O-alkylation and then hydrogenated without isolation into amines under very mild reaction conditions over standard hydrogenation catalysts. Triethyloxonium tertafluoroborate, methyl trifluoromethanesulfonate, dimethyl sulfate and ethyl chloroformate were validated as alkylating agent. The synthetic utility of this approach was demonstrated by the selective carbonyl reduction of peptide groups. Carbonyl reduction of peptide group proceeds chemoselective without racemization of the neighboring chiral center. (Figure presented.).
A BEt3-Base Catalyst for Amide Reduction with Silane
Yao, Wubing,Fang, Huaquan,He, Qiaoxing,Peng, Dongjie,Liu, Guixia,Huang, Zheng
, p. 6084 - 6093 (2019/05/24)
Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.
