10479-24-0Relevant articles and documents
Reagent concentration effects in the REM resin solid phase synthesis of tertiary amines
Morphy, J. Richard,Rankovic, Zoran,York, Mark
, p. 2137 - 2145 (2003)
The use of reagent concentration has resulted in increased rates for all stages of the REM resin synthesis of tertiary amines. These increases in rate translate into faster reaction times, higher yields and lower reagent consumption. Of the methods examin
Synthesis of Arylethylamines via C(sp3)-C(sp3) Palladium-Catalyzed Cross-Coupling
Lippa, Rhys A.,Battersby, David J.,Murphy, John A.,Barrett, Tim N.
, p. 3583 - 3604 (2021/02/27)
Substituted arylethylamines represent a key structural motif in natural, pharmaceutical, and agrochemical compounds. Access to such scaffolds has been the subject of long-standing synthetic interest. Herein, we report the synthesis of such scaffolds via a palladium-catalyzed C(sp3)-C(sp3) coupling between (chloromethyl)aryls and air-/moisture-stable N,N-dialkylaminomethyltrifluoroborate salts. Rapid hit identification was achieved using microscale high-throughput experimentation and was followed by millimolar-scale reaction parameter optimization. A range of structurally and electronically varied arylethylamine products were obtained in moderate to excellent yields (27-96%, >60 examples). The reaction mechanism is proposed to proceed via formation of a trialkylbenzylammonium species prior to oxidative addition.
Lithium-Catalyzed anti-Markovnikov Intermolecular Hydroamination Reactions of Vinylarenes and Simple Secondary Amines
Germain, Stéphane,Lecoq, Meije,Schulz, Emmanuelle,Hannedouche, Jér?me
, p. 1749 - 1753 (2017/05/26)
Various β-arylethylamine derivatives were straightforwardly obtained by the lithium-catalyzed anti-Markovnikov selective intermolecular hydroamination reaction of secondary aliphatic amines with vinylarenes. The use of only 1.5 mol % LiCH2TMS as a solid base in THF proved to be efficient to deliver the target products at room temperature with up to complete conversions. Both reaction partners were, moreover, used in equivalent amounts; thus, this protocol best respects the concepts of sustainable chemistry for the easy preparation of lead structures for pharmaceutically active compounds.