92245-13-1Relevant academic research and scientific papers
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.
Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes
Fu, Renzhong,Yang, Yang,Jin, Weihua,Gu, Hui,Zeng, Xiaojun,Chai, Wen,Ma, Yunsheng,Wang, Quan,Yi, Jun,Yuan, Rongxin
, p. 107699 - 107707 (2016/11/29)
A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.
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.
Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides
Bai, Jianfei,Zambron, Bartosz K.,Vogel, Pierre
supporting information, p. 604 - 607 (2014/04/03)
An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.
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.
