63442-83-1Relevant academic research and scientific papers
A general method for the direct transformation of common tertiary amides into ketones and amines by addition of Grignard reagents
Huang, Pei-Qiang,Wang, Yu,Xiao, Kai-Jiong,Huang, Ying-Hong
, p. 4248 - 4254 (2015/06/02)
The direct transformation of amides into ketones by addition of organometallic reagents has attracted the attention of organic chemists for a long time. However limited methods are reliable for common amides and have found synthetic applications. Here we report a method featuring in situ activation of tertiary amides with triflic anhydride (Tf2O) followed by addition of Grignard reagents. The method displays a good generality in scope for both amides and Grignard reagents, and it can be viewed as the acylation of Grignard reagents using amides as stable and selective acylating agents. Moreover, this deaminative alkylation reaction provides a mild method for the N-Deacylation of amides to give free amines.
Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate
Savarin, Cecile,Srogl, Jiri,Liebeskind, Lanny S.
, p. 3229 - 3231 (2007/10/03)
(matrix presented) Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.
