92610-10-1Relevant articles and documents
Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4N)SCF3
Scattolin, Thomas,Deckers, Kristina,Schoenebeck, Franziska
supporting information, p. 221 - 224 (2016/12/30)
Reported herein is the one-pot synthesis of trifluoromethylated amines at room temperature using the bench-stable (Me4N)SCF3reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF3with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N-CF3. The mildness and high functional group tolerance render the method highly attractive for the late-stage introduction of trifluoromethyl groups on amines, as demonstrated herein for a range of pharmaceutically relevant drug molecules.
Metal-free catalyst for the chemoselective methylation of amines using carbon dioxide as a carbon source
Das, Shoubhik,Bobbink, Felix D.,Laurenczy, Gabor,Dyson, Paul J.
supporting information, p. 12876 - 12879 (2016/02/18)
N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chemicals. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C1 building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines. The methylation of amines with CO2 as C1 source and Ph2SiH2 as reducing agent was achieved with an N-heterocyclic carbene (NHC) as the catalyst. The catalyst is tolerant toward a variety of functional groups (including esters and ethers, nitro, nitrile, and carbonyl groups, and unsaturated C-C bonds); the reaction uses commercially available reagents and can be performed on a gram scale.
An efficient and convenient palladium catalyst system for the synthesis of amines from allylic alcohols
Banerjee, Debasis,Jagadeesh, Rajenahally V.,Junge, Kathrin,Junge, Henrik,Beller, Matthias
, p. 2039 - 2044 (2013/01/15)
A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10-phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the one-step synthesis of the antifungal drug naftifine and the calcium channel blocker flunarizine. One pot is all it takes: By applying a convenient combination consisting of Pd(OAc)2/1,10- phenanthroline, a variety of allylic alcohols reacts smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity (see picture).