Intermolecular Hydroaminoalkylation of Alkynes. Issue 23 (8th February 2021)

• Record Type: Journal Article
• Authors: Kaper, Tobias; Fischer, Malte; Thye, Hermann; Geik, Dennis; Schmidtmann, Marc; Beckhaus, Ruediger; Doye, Sven
• Is Part Of: Chemistry. Volume 27:Issue 23(2021)
• Page Start: 6899
• Page End: 6903
• Publication Date: 2021-02-08
• Subjects: alkynes -- amines -- C−H activation -- hydroaminoalkylation -- titanium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202100238
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Intermolecular hydroaminoalkylation reactions of alkynes with secondary amines, which selectively give access to allylic amines with E configuration of the alkene unit, are achieved in the presence of titanium catalysts. Successful reactions of symmetrically substituted diaryl‐ and dialkylalkynes as well as a terminal alkyne take place with N ‐benzylanilines, N ‐alkylanilines, and N ‐alkylbenzylamines. Abstract : Allylic amines are directly formed from secondary amines and alkynes in the presence of highly active titanium catalysts. The corresponding hydroaminoalkylation reactions, which take place by C−H bond activation at sp 3 ‐centers in the α‐position to a nitrogen atom, can be achieved with internal and terminal alkynes, and best results are obtained with N ‐benzylaniline derivatives.