50508-50-4Relevant academic research and scientific papers
Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals
Hirata, Shuichi,Osako, Takao,Uozumi, Yasuhiro
, (2021/10/05)
We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.
Metal-Free Amidation of Acids with Formamides and T3P
Bannwart, Linda,Abele, Stefan,Tortoioli, Simone
, p. 2069 - 2078 (2016/07/06)
A new, simple and metal-free method for the direct formation of dialkylamides from carboxylic acids employing N,N-dialkylformamides as amine source is described. The one-pot reaction is promoted by propylphosphonic anhydride (T3P) in the presence of 0.5 equivalents of HCl.
