70251-03-5Relevant academic research and scientific papers
Expanding Water/Base Tolerant Frustrated Lewis Pair Chemistry to Alkylamines Enables Broad Scope Reductive Aminations
Fasano, Valerio,Ingleson, Michael J.
supporting information, p. 2217 - 2224 (2017/02/18)
Lower Lewis acidity boranes demonstrate greater tolerance to combinations of water/strong Br?nsted bases than B(C6F5)3, this enables Si?H bond activation by a frustrated Lewis pair (FLP) mechanism to proceed in the presence of H2O/alkylamines. Specifically, BPh3has improved water tolerance in the presence of alkylamines as the Br?nsted acidic adduct H2O–BPh3does not undergo irreversible deprotonation with aliphatic amines in contrast to H2O–B(C6F5)3. Therefore BPh3is a catalyst for the reductive amination of aldehydes and ketones with alkylamines using silanes as reductants. A range of amines inaccessible using B(C6F5)3as catalyst, were accessible by reductive amination catalysed by BPh3via an operationally simple methodology requiring no purification of BPh3or reagents/solvent. BPh3has a complementary reductive amination scope to B(C6F5)3with the former not an effective catalyst for the reductive amination of arylamines, while the latter is not an effective catalyst for the reductive amination of alkylamines. This disparity is due to the different pKavalues of the water–borane adducts and the greater susceptibility of BPh3species towards protodeboronation. An understanding of the deactivation processes occurring using B(C6F5)3and BPh3as reductive amination catalysts led to the identification of a third triarylborane, B(3,5-Cl2C6H3)3, that has a broader substrate scope being able to catalyse the reductive amination of both aryl and alkyl amines with carbonyls.
Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
Smith, Catherine J.,Smith, Christopher D.,Nikbin, Nikzad,Ley, Steven V.,Baxendale, Ian R.
, p. 1927 - 1937 (2011/04/21)
Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.
Trisubstituted ureas as potent and selective mPGES-1 inhibitors
Chiasson, Jean-Franois,Boulet, Louise,Brideau, Christine,Chau, Anh,Claveau, David,C?té, Bernard,Ethier, Diane,Giroux, André,Guay, Jocelyne,Guiral, Sébastien,Mancini, Joseph,Massé, Frédéric,Méthot, Nathalie,Riendeau, Denis,Roy, Patrick,Rubin, Joel,Xu, Daigen,Yu, Hongping,Ducharme, Yves,Friesen, Richard W.
experimental part, p. 1488 - 1492 (2011/04/23)
A novel series of trisubstituted ureas has been identified as potent and selective mPGES-1 inhibitors. These compounds are selective over other prostanoid enzymes such as PGF synthase and TX synthase. This series of inhibitors was developed by lead optimi
