92245-13-1Relevant articles and documents
Boric Acid Catalyzed Direct Amidation between Amino-Azaarenes and Carboxylic Acids
Yun, Fan,Cheng, Chunhui,Zhang, Jing,Li, Jingxuan,Liu, Xia,Xie, Rui,Tang, Pingwah,Yuan, Qipeng
, p. 1583 - 1596 (2017/03/21)
A novel and facile boric acid catalyzed direct amidation between amino-azaarene compounds and carboxylic acids has been developed. The amidation proceeded cleanly and provided good to excellent yields of the desired amides. Boric acid is a green and inexpensive catalyst. We have also found that N,N,N′,N′-tetramethylpropane-1,3-diamine acted as an additive accelerating this boric acid catalyzed amidation. A mixed acid anhydride is postulated to be the active intermediate responsible for this successful amidation. This direct amidation is an atom- and step-economical reaction.
Carboxyl activation via silylthioesterification: One-pot, two-step amidation of carboxylic acids catalyzed by non-metal ammonium salts
Lamar, Angus A.,Liebeskind, Lanny S.
supporting information, p. 6034 - 6037 (2015/10/28)
The first organo-catalyzed silylthioesterification of a carboxylic acid and a commercially available mercaptoorganosilane results in the in situ production of an O-silylthionoester. Subsequent amine addition forms amides in an operationally simple one-pot procedure without removal of water. The scope and efficiency of these reactions with respect to the catalyst, carboxylic acid, amine, [Si-S] moiety, and solvent are investigated. A number of functionalities are tolerated in the two-step amidation including alkene, alkyne, alkyl and aryl halides, benzylic ethers, and heterocycles with free coordinating sites.
Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide
Ko, Sangwon,Han, Hoon,Chang, Sukbok
, p. 2687 - 2690 (2007/10/03)
(Matrix presented) A strategy of chelation-assisted activation of formamide was employed to achieve hydroamidation of alkenes to generate one-carbon-elongated amides in moderate to good selectivity and yields. Also reported is the two-metal-catalyzed cooperative aminocarboxylation of aryl iodides, in which Ru is presumed to catalyze decarbonylation of formamide to release carbon monoxide and amine for the subsequent Pd-catalyzed aminocarboxylation routes, thus enabling the net transformation to be performed in the absence of external CO pressure.
