95725-04-5Relevant articles and documents
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.
Nickel-catalyzed reductive defunctionalization of esters in the absence of an external reductant: Activation of C-O bonds
Iyori, Yasuaki,Takahashi, Kenjiro,Yamazaki, Ken,Ano, Yusuke,Chatani, Naoto
supporting information, p. 13610 - 13613 (2019/11/14)
The nickel-catalyzed reductive cleavage of esters in the absence of an external reductant, which involves the cleavage of an inert acyl C-O bond in O-Alkyl esters is reported. Various groups, such as N-containing heterocycles, esters, amides, and even arene rings can function as a directing group.
Sunlight assisted direct amide formation: Via a charge-transfer complex
Cohen, Irit,Mishra, Abhaya K.,Parvari, Galit,Edrei, Rachel,Dantus, Mauricio,Eichen, Yoav,Szpilman, Alex M.
supporting information, p. 10128 - 10131 (2017/09/23)
We report on the use of charge-transfer complexes between amines and carbon tetrachloride, as a novel way to activate the amine for photochemical reactions. This principle is demonstrated in a mild, transition metal free, visible light assisted, dealkylative amide formation from feedstock carboxylic acids and amines. The low absorption coefficient of the complex allows deep light penetration and thus scale up to a gram scale.