14091-87-3Relevant academic research and scientific papers
Cross-Coupling of Secondary Amides with Tertiary Amides: The Use of Tertiary Amides as Surrogates of Alkyl Carbanions for Ketone Synthesis
Wang, Shu-Ren,Huang, Pei-Qiang
, p. 887 - 891 (2019/07/18)
In recent years, exciting progress has been made in the field of direct transformation of amides, nevertheless, the condensation between two amides remains rare and restricted to homo-coupling reactions. Herein, we report the cross-coupling of secondary amides with tertiary amides, which provides a synthesis of ketones under mild conditions, and features the use of tertiary amides as surrogates of alkyl carbanions. The method relies on the coupling of enamines, generated from tertiary amides by catalytic partial reduction of tertiary amides with Vaska's catalyst, with nitrilium ions, formed in situ from secondary amides via activation with trifluoromethanesulfonic anhydride, and on the subsequent deformylation.
Improved Titanium Tetrachloride Procedure for Enamine Synthesis.II.Scope of the Reaction
Carlson, Rolf,Nilsson, Asa
, p. 49 - 54 (2007/10/02)
The scope of enamine formation by a procedure where the carbonyl compound is added to a preformed titanium tetrachloride-amine complex was investigated with a series of different types of carbonyl compounds and two secondary amines (morpholine and pyrrolidine).The carbonyl compounds include aldehydes, cyclic ketones and some substituted aryl alkyl ketones.Yields of isolated products were in the range 67-100 percent with the exception of the pyrrolidine enamine from camphor which gave 53 percent of the isolated product.
