33925-42-7Relevant articles and documents
Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound
Chandra Sau, Mohan,Mandal, Smita,Bhattacharjee, Manish
, p. 9235 - 9245 (2021/03/16)
Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2(I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done byin situ1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceedviaη3-allyl complex formation or ally ether intermediate. The alkylation takes placeviaonly ether intermediate. The resulting allylated and alkylated products have been used for the synthesis of eleven new trisubstituted pyrazoles and one pyrazolone.
Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach
Karimzadeh, Morteza,Saberi Asl, Hamed,Hashemi, Hajar,Saberi, Dariush,Niknam, Khodabakhsh
, p. 2237 - 2244 (2018/10/31)
Abstract: Sulfamic acid stabilized on the surface of silica by the n-propyl organic group linker which is named silica-bonded N-propylsulfamic acid was applied as an efficient heterogeneous catalyst with good recyclability and reusability for direct benzylation of 1,3-dicarbonyl compounds using secondary aromatic alcohols or styrenes as alkylating agents in high yields and short reaction times. All the reactions were carried out in nitromethane as solvent under an air atmosphere. The catalyst showed reusable feature by six times without a significant loss in its activity. Graphical abstract: [Figure not available: see fulltext.].
Air-stable μ2-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application
Zhang, Xiaohong,Xu, Xinhua,Li, Ningbo,Liang, Zhiwu,Tang, Zilong
supporting information, p. 1926 - 1932 (2018/03/21)
Three air-stable zirconocene perfluoro-octanesulfonates were successfully synthesized by treatment of C8F17SO3Ag with (RCp)2ZrCl2 [R = H, n-Bu, t-Bu]. According to X-ray analysis, they have μ2-hydroxyl bridged cationic binuclear structures: (i) [CpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2THF·4H2O (1a·2THF·4H2O), (ii) [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·6H2O (2a·6H2O), and (iii) [t-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2C3H6O·8H2O (3a·2C3H6O·8H2O). The ligands of water and organic molecules in the complexes originated from the moist air and solvent during their recrystallization. These complexes were characterized with different techniques, and found to show water tolerance, air/thermal stability as well as strong Lewis acidity. Moreover, the complexes showed highly catalytic activity in various reactions of C–C bond formation. With good recyclability, they should find wide applications in organic chemistry.
Fe-catalyzed double cross-dehydrogenative coupling of 1,3-dicarbonyl compounds and arylmethanes
Yang, Kai,Song, Qiuling
supporting information, p. 548 - 551 (2015/03/05)
Fe-catalyzed tandem cross-dehydrogenative coupling of the methyl group in arylmethanes with 1,3-dicarbonyl compounds has been developed. The reaction affords one new C(sp3)-C(sp2) bond and one new C(sp3)-C(sp3)
Synthesis and structure of an air-stable bis(isopropylcyclopentadienyl) zirconium perfluorooctanesulfonate and its catalyzed benzylation of 1,3-dicarbonyl derivatives with alcohols
Zhang, Xiaohong,Qiu, Renhua,Zhou, Congcong,Yu, Jingxing,Li, Ningbo,Yin, Shuangfeng,Xu, Xinhua
, p. 1011 - 1017 (2015/01/30)
An air-stable uninuclear complex of bis(isopropylcyclopentadienyl) zirconium perfluorooctane sulfonate (1a·H2O·3THF) was successfully synthesized by the reaction of (i-PrCp)2ZrCl2 with C17SO3Ag. The c
Fe2(SO4)3·xH2O on silica: An efficient and low-cost catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions
Li, Lingjun,Zhu, Anlian,Zhang, Yuqin,Fan, Xincui,Zhang, Guisheng
, p. 4286 - 4291 (2014/01/17)
Fe2(SO4)3·xH2O on silica has been found to be a novel efficient catalyst for the direct nucleophilic substitution of alcohols in solvent-free conditions. In this reaction system, the alcohols can react with various nucleophilic reagents for the convenient construction of C-C bonds and C-N bonds with the benefits of high conversion, no requirement to use excessive amounts of the nucleophile, only a catalytic amount of iron catalyst required, solvent-free and benign reaction conditions, and the feasible reusability of the catalyst.
Yb(OTf)3-promoted effective benzylation and allylation with N-tosyl amino group as a stable leaving group
Liu, Jinqian,Wang, Limin,Zheng, Xingzhou,Wang, Aili,Zhu, Mengyun,Yu, Jianjun,Shen, Qiang
supporting information; experimental part, p. 1843 - 1846 (2012/04/23)
A simple, inexpensive, environmentally friendly, and highly efficient benzylation and allylation of 1,3-dicarbonyl compounds with sulfonamides in the presence of Yb(OTf)3 is described. Yb(OTf)3 was proved to be a good catalyst for the cleavage of sp3 carbon-nitrogen bond. Various 1,3-dicarbonyl compounds can couple with a broad range of tosyl-activated benzylic and allylic amines to give diversely functionalized products in good to excellent yields.
Sulfuric acid catalyzed addition of β-dicarbonyl compounds to alcohols under conventional heating and microwave-assisted conditions
Xia, Fei,Zhao, Zheng Le,Liu, Pei Nian
supporting information; experimental part, p. 2828 - 2832 (2012/07/17)
The highly efficient direct addition of β-dicarbonyl compounds to secondary alcohols has been achieved using one of the cheapest acids, H 2SO4, as the catalyst. For a series of β-dicarbonyl compounds and various secondary alcohols, t
Direct carbon-carbon bond formation from alcohols and active methylenes using NaHSO4/SiO2
Aoyama, Tadashi,Miyota, Saki,Takido, Toshio,Kodomari, Mitsuo
experimental part, p. 2971 - 2976 (2012/01/04)
A simple and efficient procedure for carbon-carbon bond formation has been developed starting from alcohols and active methylene-containing compounds using silica gel supported sodium hydrogen sulfate (NaHSO4/SiO 2) under mild conditions. NaHSO4/SiO2 can be reused without loss of catalytic activity at least ten times. Georg Thieme Verlag Stuttgart · New York.
Direct nucleophilic substitution reaction of alcohols mediated by a zinc-based ionic liquid
Zhu, Anlian,Li, Lingjun,Wang, Jianji,Zhuo, Kelei
experimental part, p. 1244 - 1250 (2011/06/26)
A zinc-based ionic liquid ([CHCl][ZnCl2]2) was found to be an excellent reaction medium for the direct nucleophilic substitution reactions of alcohols. The high conversion, high selectivity, easy separation procedure, catalyst reusability and no necessity of excessive nucleophiles make the chemical process cleaner. This reaction was believed to work through the carbocation mechanism and the existence of carbocation was detected by UV-vis spectroscopy. It was suggested that the hydroxyl group on the choline cation was the major inducement for the formation of special microstructures which could provide adequate stability for the carbocation in the reaction systems and increase the reactivity and selectivity.