60999-96-4Relevant articles and documents
Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
Estopi?á-Durán, Susana,McLean, Euan B.,Donnelly, Liam J.,Hockin, Bryony M.,Taylor, James E.
supporting information, p. 7547 - 7551 (2020/10/09)
The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).
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.
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
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
Highly efficient microwave-assisted substitution of β-dicarbonyl compounds with secondary alcohols using fluoroboric acid as the catalyst
Liu, Peinian,Xia, Fei,Ren, Yujie,Chen, Junqin
experimental part, p. 2075 - 2080 (2012/03/11)
The microwave-assisted substitution of β-dicarbonyl compounds with secondary alcohols has been achieved efficiently, using very cheap fluoroboric acid (HBF4) as the catalyst. For various β-dicarbonyl compounds and a series of secondary alcohols
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.
Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: Synthesis of fully decorated furans and pyrroles
Chatterjee, Paresh Nath,Roy, Sujit
experimental part, p. 4569 - 4577 (2011/07/08)
The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)] 2 catalyzes the direct substitution of hydroxyl groups in benzylic and propargylic alcohols by 1,3-dicarbonyl moiety. In 4-hydroxycoumarin, benzylation and propargylation occurs at the 3-position. Selective propargylation or allenylation takes place depending on the nature of propargylic alcohol. By applying the methodology, multi-substituted furans and pyrroles have been synthesized in good yields.
Perchloric acid catalyzed homogeneous and heterogeneous addition of β-dicarbonyl compounds to alcohols and alkenes and investigation of the mechanism
Liu, Pei Nian,Dang, Li,Wang, Qing Wei,Zhao, Shu Lei,Xia, Fei,Ren, Yu Jie,Gong, Xue Qing,Chen, Jun Qin
experimental part, p. 5017 - 5030 (2010/10/04)
(Figure presented) The direct addition of various β-dicarbonyl compounds to a series of secondary alcohols and alkenes has been achieved using 1 mol % perchloric acid (HClO4) as the catalyst. The HClO 4-catalyzed reactions could be conveniently conducted in commercial solvent and gave moderate to excellent yields. Moreover, the silica gel-supported HClO4 could also catalyze the heterogeneous addition for a series of substrates with similar or even higher yields in comparison with the homogeneous ones. The supported catalyst could be readily recovered and reused for four runs. Furthermore, the mechanism of the HClO4- catalyzed addition of the β-diketone to alcohol was investigated, and an SN1 mechanism was proved unambiguously for the first time through a series of experiments. The discrimination of catalytic abilities among different Bronsted acids was also rationalized by DFT calculations.
Triflic acid adsorbed on silica gel as an efficient and recyclable catalyst for the addition of β-dicarbonyl compounds to alcohols and alkenes
Liu, Pei Nian,Xia, Fei,Wang, Qing Wei,Ren, Yu Jie,Chen, Jun Qin
supporting information; experimental part, p. 1049 - 1055 (2010/08/04)
The silica gel supported triflic acid was readily prepared via simple absorption of TfOH onto chromatographic silica gel. This solid acid was applied as an efficient catalyst for the heterogeneous addition of various β-dicarbonyl compounds to a series of alcohols and alkenes, which afforded moderate to excellent yields under solvent-free conditions or in nitromethane. Moreover, this silica gel supported catalyst surprisingly exhibited higher reaction yields in comparison with the homogeneous catalyst and can be readily recovered and reused up to 6 times with almost maintained reactivity and yields.
Catalytic alkylation of benzylic C-H bonds with 1,3-dicarbonyl compounds utilizing oxygen as terminal oxidant
Correia, Camille A.,Li, Chao-Jun
body text, p. 1172 - 1175 (2010/04/23)
The oxidative alkylation of benzylic C-H bonds with 1,3-dicarbonyl compounds was developed using oxygen as the terminal oxidant in the presence of catalytic amounts of FeCl2, CuCl and NHPI.