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Theoretical Studies on the Hydroaminoalkylation of Alkenes with Primary and Secondary Amines
Author(s) -
Stelter Luisa,
Teusch Thomas,
Bielefeld Jens,
Doye Sven,
Klüner Thorsten
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802699
Subject(s) - primary (astronomy) , dimethylamine , methylamine , alkylation , chemistry , intermolecular force , catalysis , organic chemistry , computational chemistry , combinatorial chemistry , molecule , physics , astronomy
The α‐alkylation of amines with alkenes catalyzed by early transition‐metal complexes represents an efficient and atom economic method for the synthesis of functionalized amines from simple and easily available starting materials. While the successful use of secondary amines, such as dimethylamine, strongly underlines the enormous industrial potential of this reaction, the analogous intermolecular α‐alkylation of primary amines, especially methylamine, remains an unsolved synthetic task to this day. Based on calculated thermodynamic data, these experimental findings can now be explained for the first time, whereby several competing reactions, which are explained in detail, are of crucial importance for the different behavior of primary and secondary amines.