128352-65-8Relevant articles and documents
Lewis acid catalysis by lanthanide complexes with tris(perfluorooctanesulfonyl)methide ponytails in fluorous recyclable phase
Mikami, Koichi,Mikami, Yutaka,Matsumoto, Yousuke,Nishikido, Joji,Yamamoto, Fumihiko,Nakajima, Hitoshi
, p. 289 - 292 (2001)
Scandium and ytterbium tris(perfluorooctanesulfonyl)methide complexes are shown to be immobilized in fluorous recyclable phase and extremely efficient Lewis acid catalysts for alcohol acylation, Friedel-Crafts acylation, Diels-Alder reaction, and Mukaiyam
A Well-Defined Aluminum-Based Lewis Acid as an Effective Catalyst for Diels-Alder Transformations
Liu, Zhizhou,Lee, Jazreen Hui Qi,Ganguly, Rakesh,Vidovic, Dragoslav
, p. 11344 - 11348 (2015)
A catalytically active aluminum-based system for Diels-Alder transformations is reported. The system was generated by mixing a β-diketiminate-stabilized aluminum bistriflate compound with Na[BArCl4] (ArCl=3,5-Cl2C6H3). Solid-state analysis of the catalytic system reveals a unique structure incorporating a two-dimensional coordination polymer. According to the experimental results obtained from several Diels-Alder transformations, the aluminum-based system appears to be a more practical and more robust alternative to the recently reported compounds based on carbon and silicon cations.
Difluorotris(pentafluoroethyl)phosphorane - A highly active catalyst for Diels-Alder reaction
Bittner, Bozena,Koppe, Karsten,Bilir, Vural,Frank, Walter,Willner, Helge,Ignatev, Nikolai
, p. 50 - 60 (2015)
Difluorotris(pentafluoroethyl)phosphorane, (C2F5)3PF2, was found to catalyze Diels-Alder reactions of α,β-unsaturated ketones or aldehydes with conjugated dienes or cyclodienes providing the cycloaddition products in high yields. Only a small quantity of this catalyst is required to complete the Diels-Alder reaction. The developed protocol is more convenient than the procedures reported in the literature. Several cyclohexene, naphthalene and norbornene derivatives were obtained in moderate to good yields.
Synthese organique sous champ microondes: Premier exemple d'activation specifique en phase homogene
Berlan,Giboreau,Lefeuvre,Marchand
, p. 2363 - 2366 (1991)
The rate of several Diels-Alder reactions under conventional or microwave heating are compared at the same bulk temperature. This afford the first evidence for a specific activating effect of microwaves under homogeneous conditions.
3-Methoxybutan-2-one as a sustainable bio-based alternative to chlorinated solvents
Byrne, Fergal P.,Clark, James H.,Hunt, Andrew J.,Jin, Saimeng,McElroy, Con Robert,Quinn, Alex,Sherwood, James
, p. 39412 - 39419 (2021/12/24)
Methylation of acetoin with dimethyl carbonate was performed in a sustainable one-step process, with improved process mass intensity (PMI) and atom economy compared to previously published methods. The resulting product, 3-methoxybutan-2-one (MO) was succ
Strongly Lewis Acidic Metal-Organic Frameworks for Continuous Flow Catalysis
Ji, Pengfei,Feng, Xuanyu,Oliveres, Pau,Li, Zhe,Murakami, Akiko,Wang, Cheng,Lin, Wenbin
supporting information, p. 14878 - 14888 (2019/10/02)
The synthesis of highly acidic metal-organic frameworks (MOFs) has attracted significant research interest in recent years. We report here the design of a strongly Lewis acidic MOF, ZrOTf-BTC, through two-step transformation of MOF-808 (Zr-BTC) secondary building units (SBUs). Zr-BTC was first treated with 1 M hydrochloric acid solution to afford ZrOH-BTC by replacing each bridging formate group with a pair of hydroxide and water groups. The resultant ZrOH-BTC was further treated with trimethylsilyl triflate (Me3SiOTf) to afford ZrOTf-BTC by taking advantage of the oxophilicity of the Me3Si group. Electron paramagnetic resonance spectra of Zr-bound superoxide and fluorescence spectra of Zr-bound N-methylacridone provided a quantitative measurement of Lewis acidity of ZrOTf-BTC with an energy splitting (?E) of 0.99 eV between the ?x? and ?y? orbitals, which is competitive to the homogeneous benchmark Sc(OTf)3. ZrOTf-BTC was shown to be a highly active solid Lewis acid catalyst for a broad range of important organic transformations under mild conditions, including Diels-Alder reaction, epoxide ring-opening reaction, Friedel-Crafts acylation, and alkene hydroalkoxylation reaction. The MOF catalyst outperformed Sc(OTf)3 in terms of both catalytic activity and catalyst lifetime. Moreover, we developed a ZrOTf-BTC?SiO2 composite as an efficient solid Lewis acid catalyst for continuous flow catalysis. The Zr centers in ZrOTf-BTC?SiO2 feature identical coordination environment to ZrOTf-BTC based on spectroscopic evidence. ZrOTf-BTC?SiO2 displayed exceptionally high turnover numbers (TONs) of 1700 for Diels-Alder reaction, 2700 for epoxide ring-opening reaction, and 326 for Friedel-Crafts acylation under flow conditions. We have thus created strongly Lewis acidic sites in MOFs via triflation and constructed the MOF?SiO2 composite for continuous flow catalysis of important organic transformations.