6876-65-9Relevant academic research and scientific papers
Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong
supporting information, p. 6227 - 6232 (2021/07/28)
N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
Palladium Catalyzed Aminocarbonylation of Benzylic Ammonium Triflates with Nitroarenes: Synthesis of Phenylacetamides
Yang, Li-Miao,Li, Shan-Shan,Zhang, You-Ya,Lu, Jin-Liang,Deng, Jing-Tong,Ma, Ai-Jun,Zhang, Xiang-Zhi,Zhang, Shu-Yu,Peng, Jin-Bao
supporting information, p. 2061 - 2065 (2021/02/26)
A palladium catalyzed reductive aminocarbonylation of benzylic ammonium triflates with nitroarenes for the synthesis of phenylacetamides was developed. Using Pd(acac)2/DPPF catalyst system, a range of different substituted phenylacetamides were prepared in moderate to good yields from benzylic ammonium triflates and nitroarenes through Csp3?N bond cleavage. A variety of alkyl, aryl, and halide substituents on both substrates can be used, and many useful functional groups can be tolerated. (Figure presented.).
Nickel (II)-Catalyzed efficient aminocarbonylation of unreactive alkanes with formanilides—Exploiting the deformylation behavior of imides
Han, Zhang,Chaowei, Dai,Lice, Liu,Hongfei, Ma,Hongzhong, Bu,Yufeng, Li
, p. 3712 - 3718 (2018/05/29)
Challenging functionalization of C(sp3)-H has recently attracted much attention of organic chemists. In this paper, we developed a Ni(acac)2-catalyzed activation of unreactive alkanes with formanilides in the presence of carbon monoxide to furnish moderate to excellent yields of amides. This is the first example of aminocarbonylation of inert alkanes using nickel-based catalyst, and formanilides is disclosed to be an interesting amine source owing to the peculiar deformylation nature of imide intermediates.
Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
, p. 3099 - 3103 (2018/05/22)
An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
Yang, Yu,Ren, Hong-Xia,Chen, Feng,Zhang, Zheng-Bing,Zou, Ying,Chen, Chao,Song, Xiang-Jia,Tian, Fang,Peng, Lin,Wang, Li-Xin
supporting information, p. 2805 - 2808 (2017/06/07)
An unusual and highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and excellent stereoselectivities (up to >99:1 dr and >99% ee). The efficiency and potentials of the new reaction and the target chiral entities were well demonstrated by delicate transformations into a series of new chiral indolines.
Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides
De, Subhadip,Yin, Junli,Ma, Dawei
supporting information, p. 4864 - 4867 (2017/09/23)
Cu2O/N,N′-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramolecular cross-coupling product.
Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides
Panahi, Farhad,Jamedi, Fereshteh,Iranpoor, Nasser
, p. 780 - 788 (2017/01/18)
A Nickel-catalyzed reductive process is described for the direct amidation of benzyl and aryl halides using carbodiimides as the amidating agent. Moreover, aryl and benzyl C–O electrophiles such as triflate, acetate, tosylate, trityl ether, and pivalate were converted into amides using this method. The in-situ-generated Ni0acts as a catalyst for the reaction at room temperature for benzylic substrates, and 70 °C for aryl electrophiles. This new nickel-catalyzed reductive coupling protocol provides a general and operationally simple method for the synthesis of diverse amides using carbodiimides. Amides bearing bulky substituents can be synthesized by this strategy in high yield, which demonstrates its effectiveness in amide synthesis.
Novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture
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Paragraph 0036-0038, (2017/04/19)
The invention provides a novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture. The structure of the compound is expressed by methods such as H NMR, C, NMR and HRMS and is confirmed. A series of phenmethyl quaternary ammonium salts and aminated compounds are used; under the catalysis effect of PdCl2(dppf), PPh3 is used as a ligand, Na2CO3 is used as the alkali, and corresponding amide compounds are generated in the 100-DEG C CO atmosphere in a pHMe/DMSO mixed solvent. The method has the advantages that the efficiency is high; the toxicity is low; the conditions are mild; the application range of the substrate is wide; the yield is high; the product purity is high; the separation is convenient; the method can be applicable to large-scale preparation; the application prospects are wide.
Metal-free hydration of ynamides: Convenient approach to amides
Huang, Hai,Tang, Luning,Xi, Yang,He, Guangke,Zhu, Hongjun
supporting information, p. 1873 - 1876 (2016/04/19)
The trifluoroacetic acid (TFA) mediated hydration of ynamides was developed, which is an efficient approach for the synthesis of N-monosubstituted amides. This convenient method is effective with a wide range of substrates under room temperature condition, and the products are obtained in high to excellent yields through an easy work-up process.
A simple and greener approach for the amide bond formation employing FeCl3 as a catalyst
Basavaprabhu,Muniyappa, Krishnamurthy,Panguluri, Nageswara Rao,Veladi, Panduranga,Sureshbabu, Vommina V.
supporting information, p. 7746 - 7749 (2015/10/12)
Catalytic use of FeCl3 in the presence of glacial AcOH for the direct amidation of acid with amine in toluene has been described in this paper. The protocol worked well for the less nucleophilic aniline and its variants which gave the best results under the present reaction conditions. Amidation of bromoacetic acid and sterically hindered amino acid also proceed effectively to yield the corresponding amides. The protocol is catalytic and circumvents the use of stoichiometric amounts of reagents. The reaction led to water soluble by-products and thus makes the product isolation easier.
