91888-96-9Relevant academic research and scientific papers
A convenient synthesis of N-tert-butyl amides by the reaction of di-tert-butyl dicarbonate and nitriles catalyzed by Cu(OTf)2
Chen, Junqing,Feng, Chengliang,Ji, Min,Tang, Yuqi,Yang, Wanfeng
, p. 602 - 608 (2020/04/27)
The utility of Cu(OTf)2 as the catalyst for the synthesis of a series of N-tert-butyl amides in excellent isolated yields via the reaction of nitriles (alkyl, aryl, benzyl, and furyl nitriles) with di-tert-butyl dicarbonate is described. Cu(OTf)2 is a highly stable and efficient catalyst for the present Ritter reaction under solvent-free conditions at room temperature.
Nickel-catalyzed aminocarbonylation of Aryl/Alkenyl/Allyl (pseudo)halides with isocyanides and H2O
Li, Qiao,Cai, Yun,Jin, Hongwei,Liu, Yunkui,Zhou, Bingwei
supporting information, (2020/11/27)
Herein described is a nickel-catalyzed aminocarbonylation of aryl/alkenyl/allyl (pseudo)halides with isocyanides, providing aryl/alkenyl/allyl amides in 41% to 92% yields. Functional groups such as F, Cl, OMe, and heteroaromatic rings are compatible in the reaction. A Ni(0)/Ni(II) catalytic cycle is proposed based on preliminary experiments and previous literature. The reaction features readily available nickel salt, broad functional group tolerance, and simple reaction conditions.
Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
Alandini, Nurtalya,Buzzetti, Luca,Candish, Lisa,Collins, Karl D.,Favi, Gianfranco,Melchiorre, Paolo,Schulte, Tim
supporting information, p. 5248 - 5253 (2020/03/03)
Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.
An efficient synthesis of N-tert-butyl amides by the reaction of tert-butyl benzoate with nitriles catalyzed by Zn(ClO4)2·6H2O
Feng, Cheng-Liang,Yan, Bin,Zhang, Min,Chen, Jun-Qing,Ji, Min
, p. 535 - 542 (2019/02/12)
An efficient, mild and inexpensive synthesis of N-tert-butyl amides from the reaction of nitriles (aryl, benzyl and sec-alkyl nitriles) with tert-butyl benzoate catalyzed by the employment of 2?mol% Zn(ClO4)2·6H2O at 50?°C
Transamidation of: N -acyl-glutarimides with amines
Liu, Yongmei,Achtenhagen, Marcel,Liu, Ruzhang,Szostak, Michal
, p. 1322 - 1329 (2018/03/06)
The development of new transamidation reactions for the synthesis of amides is an important and active area of research due to the central role of amide linkage in various fields of chemistry. Herein, we report a new method for transamidation of N-acyl-glutarimides with amines under mild, metal-free conditions that relies on amide bond twist to weaken amidic resonance. A wide range of amines and functional groups, including electrophilic substituents that would be problematic in metal-catalyzed protocols, are tolerated under the reaction conditions. Mechanistic experiments implicate the amide bond twist, thermodynamic stability of the tetrahedral intermediate and leaving group ability of glutarimide as factors controlling the reactivity of this process. The method further establishes the synthetic utility of N-acyl-glutarimides as bench-stable, twist-perpendicular, amide-based reagents in acyl-transfer reactions by a metal-free pathway. The origin of reactivity of N-acyl-glutarimides in metal-free and metal-catalyzed processes is discussed and compared.
Organic template-free synthesis of zeolite Y nanoparticle assemblies and their application in the catalysis of the Ritter reaction
Tang, Ting,Zhang, Lei,Dong, Hai,Fang, Zhongxue,Fu, Wenqian,Yu, Quanyong,Tang, Tiandi
, p. 7711 - 7717 (2017/02/05)
Zeolite Y nanoparticle assemblies (Y-NA) with a mesoporous structure were directly synthesized at 75?°C for 16 h without adding any organic templates. The changes in structure, morphology and textural parameters of the materials obtained after different crystallization times were investigated via powder X-ray diffraction (XRD), infrared spectroscopy (IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and N2-sorption. The results show that Y-NA had a micro-mesoporous structure composed of highly crystalline particle assemblies with sizes of 400-900 nm. The H-form Y-NA (HY-NA) is strongly acidic, and exhibits a good catalytic performance in the Ritter reaction, as compared with the H-form microporous zeolite Y and mesoporous zeolite ZSM-5.
Efficient Approach to Amide Bond Formation with Nitriles and Peroxides: One-Pot Access to Boronated β-Ketoamides
Gore, Babasaheb Sopan,Senadi, Gopal Chandru,Garkhedkar, Amol Milind,Wang, Jeh-Jeng
supporting information, p. 3014 - 3021 (2017/09/08)
An efficient, mild and practical approach for the synthesis of amides from nitriles and peroxides is reported in the presence of boron trifluoride ethereate. In this protocol, we utilized peroxides as C1 synthons for the amidation reaction. Als
Palladium/Copper-Catalyzed Oxidative Coupling of Arylboronic Acids with Isocyanides: Selective Routes to Amides and Diaryl Ketones
Lu, Fangling,Chen, Ziyue,Li, Zhen,Wang, Xiaoyan,Peng, Xinyue,Li, Cong,Fang, Lingtong,Liu, Dong,Gao, Meng,Lei, Aiwen
supporting information, p. 3954 - 3957 (2017/08/14)
An efficient and alternative oxidative cross-coupling strategy starting from arylboronic acids and isocyanides for the selective synthesis of amides and diaryl ketones with palladium/copper catalysis is developed. Various substituted benzamides and benzop
Bu4NI-Catalyzed Oxygen-Centered Radical Addition between Acyl Peroxides and Isocyanides
Chen, Meng,Li, Yang,Tang, Hong,Ding, Hao,Wang, Kai,Yang, Lingen,Li, Cuiting,Gao, Meng,Lei, Aiwen
supporting information, p. 3147 - 3150 (2017/06/23)
A novel oxygen-centered radical addition between acyl peroxides and isocyanides has been developed. A diverse collection of valuable arylcarboxyamides were easily synthesized by this protocol. From the preliminary mechanistic study, the elimination of carbon dioxide affords the product via an intramolecular rearrangement.
Cp?CoIII-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks
Bera, Sourav Sekhar,Debbarma, Suvankar,Ghosh, Avick Kumar,Chand, Santanu,Maji, Modhu Sudan
, p. 420 - 430 (2017/04/26)
Hydroarylation of internal alkynes by cost-effective CoIII-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.
