2944-97-0Relevant 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.
Exhaustive Chemoselective Reduction of Nitriles by Catalytic Hydrosilylation Involving Cooperative Si-H Bond Activation
Wübbolt, Simon,Oestreich, Martin
supporting information, p. 2411 - 2414 (2017/10/03)
A chemoselective method for the catalytic hydrosilylation of nitriles to either the imine or amine oxidation level is reported. The chemoselectivity is controlled by the hydrosilane used. The usefulness of the nitrile-to-amine reduction is demonstrated for a diverse set of aromatic and aliphatic nitriles, and the amines are easily isolated after hydrolysis as their hydrochloride salts. This exhaustive nitrile reduction proceeds at room temperature.
A proton-switchable bifunctional ruthenium complex that catalyzes nitrile hydroboration
Geri, Jacob B.,Szymczak, Nathaniel K.
, p. 12808 - 12814 (2015/10/28)
A new bifunctional pincer ligand framework bearing pendent proton-responsive hydroxyl groups was prepared and metalated with Ru(II) and subsequently isolated in four discrete protonation states. Stoichiometric reactions with H2 and HBPin showed facile E-H (E = H or BPin) activation across a Ru(II)-O bond, providing access to unusual Ru-H species with strong interactions with neighboring proton and boron atoms. These complexes were found to promote the catalytic hydroboration of ketones and nitriles under mild conditions, and the activity was highly dependent on the ligand's protonation state. Mechanistic experiments revealed a crucial role of the pendent hydroxyl groups for catalytic activity.
Hydrosiloxane-Ti(OiPr)4: An efficient system for the reduction of primary amides into primary amines as their hydrochloride salts
Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Favre-Réguillon, Alain,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
experimental part, p. 4072 - 4075 (2011/09/12)
A simple and useful method for the reduction of primary amides into the corresponding amines using a polymethylhydrosiloxane (PMHS)-Ti(OiPr)4 reducing system is described. Aromatic as well as aliphatic primary amides are reduced in high selectivity and excellent yields. The reduction could proceed via dehydration of the primary amide group into the corresponding nitrile which is then reduced into the corresponding primary amine.
