34946-13-9Relevant academic research and scientific papers
Catalytic Staudinger Reduction at Room Temperature
Lenstra, Danny C.,Wolf, Joris J.,Mecinovi?, Jasmin
, p. 6536 - 6545 (2019/05/24)
We report an efficient catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides over other common functionalities, including nitriles, alkenes, alkynes, esters, and ketones.
Sustainable organophosphorus-catalysed Staudinger reduction
Lenstra, Danny C.,Lenting, Peter E.,Mecinovi?, Jasmin
supporting information, p. 4418 - 4422 (2018/10/17)
A highly efficient and sustainable catalytic Staudinger reduction for the conversion of organic azides to amines in excellent yields has been developed. The reaction displays excellent functional group tolerance to functionalities that are otherwise prone to reduction, such as sulfones, esters, amides, ketones, nitriles, alkenes, and benzyl ethers. The green nature of the reaction is exemplified by the use of PMHS, CPME, and a lack of column chromatography.
Reaction of azides with trimethyl phosphite in the presence of water: a chemoselective synthesis of functionalized phosphoramidates
Zidani, A.,Carrie, R.,Vaultier, M.
, p. 71 - 75 (2007/10/02)
The reductive phosphorylation of azides with trimethyl phosphite and water in THF leads to the corresponding phosphoramidates which are protected primary amines in excellent yields.The P-N bond in these derivatives may be easily cleft in acidic medium to give the primary amine salts.Some examples are reported.The bis-anion 4 obtained by metallation of 3b is C-alkylated at low temperature leading to new phosphoramidates. 3i and 3j derived from α-azidoketones could not be transformed into the corresponding α-aminoketone salts.The use of methyl diphenylphosphinite in place of trimethyl phosphite leads to the diphenylphosphinamide 7 which, when treated with para-toluenesulfonic acid monohydrate in ether, gives the corresponding α-aminoacetone salt 8 in good yield.Keywords: azides / reductive phosphorylation / phosphoramidates / chemoselective reduction / functionalized primary amines
