24059-72-1Relevant academic research and scientific papers
Ruthenium-catalyzed synthesis of: N -substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines
Zheng, Yanling,Nie, Xufeng,Long, Yang,Ji, Li,Fu, Haiyan,Zheng, Xueli,Chen, Hua,Li, Ruixiang
supporting information, p. 12384 - 12387 (2019/10/19)
Herein, we report the first example of synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step, which was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene-phosphine-phosphine ligand as the catalyst.
Selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles: Via the ring contraction and deformylative functionalization of piperidine derivatives
Wang, Fang,Zhang, Xinying,He, Yan,Fan, Xuesen
, p. 156 - 164 (2019/01/08)
In this paper, a selective synthesis of pyrrolidin-2-ones and 3-iodopyrroles via the cascade reactions of N-substituted piperidines is presented. Mechanistically, the formation of pyrrolidin-2-ones involves a domino process including the in situ formation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation and ipso-oxidation. On the other hand, 3-iodopyrroles are believed to be formed via the initial generation of pyrrolidine-2-carbaldehyde followed by carboxylic acid formation, decarboxylation, dehydrogenation, iodination and aromatization. Interestingly, either pyrrolidin-2-ones or 3-iodopyrroles could be obtained selectively from the same substrates, and the selectivity was easily tuned by using a specific oxidant and additive.
Pyrrolidone compound synthesis method
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Paragraph 0069-0071, (2019/03/08)
The invention discloses a pyrrolidone compound synthesis method, and belongs to the technical field of organic synthesis. Saturated cyclic tertiary amine 1 is added into solvents, and heating reactionis performed in the presence of oxidizing agent, cupric salt, potassium hydrogen persulfate compound salt (Oxone) and oxygen mixture, additives, elementary iodine or iodated metal salt and the like to obtain pyrrolidone 2. According to the method, a pyrrolidone compound is synthesized by cascade reaction of oxidization retraction, decarbonylation and in-situ oxidization of saturated cyclic tertiary amine compounds, the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and an economical, practical, green and environment-friendly novel method is provided for synthesis of the pyrrolidone compound.
Aluminium Chloride-Mediated Synthesis of 1-Chloro-2,2,2-Trifluoroethylidene-Substituted Pyrrolidones
Wang, Zeng,Yuan, Zihang,Han, Xiaoyan,Weng, Zhiqiang
supporting information, p. 2178 - 2182 (2018/04/25)
An aluminium chloride-mediated cascade reaction between pyrrolidones and trifluoroacetic anhydride is reported. Functionally diverse 1-chloro-2,2,2-trifluoroethylidene-substituted pyrrolidones were obtained in moderate to high yields through electrophilic trifluoroacetylation, nucleophilic chlorination, and elimination. This procedure has a wide scope, good functional-group tolerance and the reaction conditions are amenable to scale up. Additionally the obtained 1-chloro-2,2,2-trifluoroethylidene products can be applied to further functionalization as trifluoromethyl-containing building blocks. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). (Figure presented.).
Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols
Chen, Jiangbo,Wang, Jiaquan,Tu, Tao
, p. 2559 - 2565 (2018/07/30)
By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.
Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions
Chen, Mao,Ichikawa, Saki,Buchwald, Stephen L.
, p. 263 - 266 (2015/02/05)
A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.
Buchwald-Hartwig reactions in water using surfactants
Salomé, Christophe,Wagner, Patrick,Bollenbach, Maud,Bihel, Frédéric,Bourguignon, Jean-Jacques,Schmitt, Martine
, p. 3413 - 3421 (2014/05/06)
Examination of the scope and limitation of the Buchwald-Hartwig cross-coupling reaction in micellar medium is reported. An array of aryl or heteroaryl halides were coupled to diverse nitrogen coupling partners using a combination of [(allyl)PdCl]2 and cBRIDP to afford the corresponding products in moderate to excellent yields. 30 examples are reported, including polar solid and fairly water-soluble organic substrates/reagents.
Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water
Yong, Fui-Fong,Teo, Yong-Chua,Chua, Guan-Leong,Lim, Gina Shiyun,Lin, Yizhen
supporting information; experimental part, p. 1169 - 1172 (2011/03/21)
A convenient and efficient protocol has been developed for the cross-coupling of amides and aryl iodides using a ligand-free copper(I) oxide catalyst in water. A variety of amide derivatives afforded the corresponding N-arylated products in moderate to good yields (up to 88%).
Cobalt-catalyzed N-arylation of nitrogen nucleophiles in water
Teo, Yong-Chua,Chua, Guan-Leong
supporting information; experimental part, p. 3072 - 3075 (2009/12/05)
The first cobalt-catalyzed N-arylation of nitrogen heterocycles with electrophilic aryl halides in water mediated by a combination of readily available and cheap CoCl2·6H2O with the chelating diamine was reported. Investigation of the ligand system show that the reaction proceeds through a biphasic system with the best yield achieved when the reaction is carried out using a combination of CoCl2·6H 2O and N,N'-dimethylethylenediamine (dmeda). Aryl iodides are found to be more reactive than aryl bromides as electophilic counterpart in the coupling reactions, producing the products in much higher yields. Heterocycles, such as indole and 7-azaindole are found to be effective nucleophilic counterparts for the coupling process and produce N-phenyl derivatives.
Efficient cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
Teo, Yong-Chua
supporting information; experimental part, p. 720 - 724 (2009/11/30)
A facile and practical strategy has been developed for the N-arylation of nitrogen nucleophiles with aryl halides catalyzed by a combination of iron(III) chloride [FeCl3] and dimethylethylenediamine (dmeda) in water. A variety of nitrogen nucleophiles including pyrazole, indole, 7-azaindole and benzamide afforded the N-arylated products in the presence of the catalytic system (in up to 88% yield).
