16350-96-2Relevant academic research and scientific papers
Rapid and efficient access to secondary arylmethylamines
Fleury-Brégeot, Nicolas,Raushel, Jessica,Sandrock, Deidre L.,Dreher, Spencer D.,Molander, Gary A.
, p. 9564 - 9570 (2012/08/28)
Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes. Secondary ammoniomethyltrifluoroborates can be easily synthesized by nucleophilic substitution on potassium bromomethyltrifluoroborate. These reagents have then been used in Suzuki-Miyaura cross-couplings with aryl bromides, offering an effective access to the aminomethylarene structural motif. This new method provides an interesting alternative to the reductive amination procedure (see scheme). Copyright
Self-modulated highly chemoselective direct-reductive-amination (DRA) of benzaldehydes straightforward to N-monosubstituted benzylamine hydrochlorides
Xing, Lixin,Cheng, Chuanjie,Zhu, Rui,Zhang, Boyang,Wang, Xinyan,Hu, Yuefei
supporting information; experimental part, p. 11783 - 11788 (2009/04/05)
An unprecedented efficient and chemoselective DRA of benzaldehydes and primary amines was developed to directly yield N-monosubstituted benzylamine hydrochlorides as single products in practically quantitative yields. The method was characterized by simply adding a few milliliters of CHCl3 in the conventional Pd-C catalytic hydrogenation system at atmospheric pressure and room temperature. A self-modulated system and a four-stage cyclic pathway were proposed.
The N-Substitution of Aliphatic Primary Amines via 1-benzotriazoles: Preparation of Secondary Amines
Katritzky, Alan R.,Glen, Noble,Pilarski, Boguslaw,Harris, Philip
, p. 1443 - 1446 (2007/10/02)
A new method has been developed for the selective conversion of primary aliphatic amines into unsymmetrical secondary amines by Grignard reaction of 1-benzotriazoles 1.This method employs simple procedures and mild conditions, and is specific in that onyl monoalkylation of the primary amines results.
ETUDE DE LA CHIMIOSELECTIVITE DE LA REACTION DES DICHLOROBORANES AVEC LES AZIDES FONCTIONNELS: UNE SYNTHESE EFFICACE D'AMINES SECONDAIRES FONCTIONNALISEES.
Carboni, B.,Vaultier, M.,Carrie, R.
, p. 1799 - 1810 (2007/10/02)
The reaction of cyclohexyldichloroborane, used as a model, with a wide variety of functionalized azides has been studied.It has been shown to be an efficient synthesis of secondary amines in terms of chemioselectivity, yields and wide applicability.
