72443-66-4Relevant academic research and scientific papers
Tertiary amine synthesis: Via reductive coupling of amides with Grignard reagents
Xie, Lan-Gui,Dixon, Darren J.
, p. 7492 - 7497 (2017/10/30)
A new iridium catalyzed reductive coupling reaction of Grignard reagents and tertiary amides affording functionalised tertiary amine products via an efficient and technically-simple one-pot, two-stage experimental protocol, is reported. The reaction-which can be carried out on gram-scale using as little as 1 mol% Vaska's complex [IrCl(CO)(PPh3)2] and TMDS as the terminal reductant for the initial reductive activation step-tolerates a broad range of tertiary amides from (hetero)aromatic to aliphatic (branched, unbranched and formyl) and a wide variety of alkyl (linear, branched), vinyl, alkynyl and (hetero)aryl Grignard reagents. The new methodology has been applied directly to bioactive molecule synthesis and the high chemoselectivity of the reductive coupling of amide has been exploited in late stage functionalization of drug molecules. This reductive functionalisation of tertiary amides provides a new and practical solution to tertiary amine synthesis.
Action d'organometalliques fonctionnels sur des gem-aminoethers et des sels d'immonium. I. Synthese d'amines α- ou β-fonctionnelles difficilement accessibles par reaction de Mannich
Courtois, Gilles,Miginiac, Philippe
, p. 395 - 400 (2007/10/02)
Some α- or β-functional amines which are difficult to obtain by Mannich reaction can be easily prepared from organomagnesium or organozinc functional derivatives and gem-aminoethers or immonium salts.
Ylide Reactions of Benzyldimethylammonium Halides
Sato, Yoshiro,Yagi, Yoko,Koto, Masami
, p. 613 - 617 (2007/10/02)
Deprotonation of benzyldimethylammonium halides (10) with sodium amide or n-butyllithium afforded silylated ylide intermediates 11, which were rearranged into N,N-dimethyl-2-benzylamines (13) accompanied by the formation of Sommelet-Hauser and Stevens rearrangement products (12 and 22).The ylide formation by the cleavage of carbon-silicon bonds also is discussed in the reaction of 10 with sodium amide and lithium aluminum hydride.
