Carbon Dioxide-Mediated Catalytic Rearrangement of Propargyl Alcohols into α,β-Unsaturated Ketones

2007 ◽  
Vol 129 (43) ◽  
pp. 12902-12903 ◽  
Author(s):  
Yudai Sugawara ◽  
Wataru Yamada ◽  
Shunsuke Yoshida ◽  
Taketo Ikeno ◽  
Tohru Yamada
Keyword(s):  
Carbon Dioxide ◽  
Unsaturated Ketones ◽  
Propargyl Alcohols

ChemInform Abstract: Carbon Dioxide Mediated Catalytic Rearrangement of Propargyl Alcohols into α,β-Unsaturated Ketones.

ChemInform ◽  
2008 ◽  
Vol 39 (9) ◽  
Author(s):  
Yudai Sugawara ◽  
Wataru Yamada ◽  
Shunsuke Yoshida ◽  
Taketo Ikeno ◽  
Tohru Yamada
Keyword(s):  
Carbon Dioxide ◽  
Unsaturated Ketones ◽  
Propargyl Alcohols

Effective Guanidine-Catalyzed Synthesis of Carbonate and Carbamate Derivatives from Propargyl Alcohols in Supercritical Carbon Dioxide

2011 ◽  
Vol 353 (1) ◽  
pp. 133-146 ◽  
Author(s):  
Nicola Della Ca' ◽  
Bartolo Gabriele ◽  
Giuseppe Ruffolo ◽  
Lucia Veltri ◽  
Tito Zanetta ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Supercritical Carbon Dioxide ◽  
Supercritical Carbon ◽  
Propargyl Alcohols

scholarly journals Phosphine-catalyzed fixation of CO2 with γ-hydroxyl alkynone under ambient temperature and pressure: kinetic resolution and further conversion

2019 ◽  
Vol 6 (14) ◽  
pp. 2420-2429 ◽  
Author(s):  
Yao-Liang Sun ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Carbon Dioxide ◽  
Ambient Temperature ◽  
Kinetic Resolution ◽  
Carbon Dioxide Fixation ◽  
Temperature And Pressure ◽  
Propargyl Alcohols

Phosphine-catalyzed fixation of CO2 with γ-hydroxyl alkynone under ambient temperature and pressure was achieved and the first example of chiral phosphine catalyzed kinetic resolution of propargyl alcohols via carbon dioxide fixation was demonstrated.

Distillable ionic liquids for a new multicomponent reaction

2007 ◽  
Vol 79 (11) ◽  
pp. 1869-1877 ◽  
Author(s):  
Anthony E. Rosamilia ◽  
Christopher R. Strauss ◽  
Janet L. Scott
Keyword(s):  
Carbon Dioxide ◽  
Ionic Liquid ◽  
Ionic Liquids ◽  
Multicomponent Reaction ◽  
Reaction Medium ◽  
Building Blocks ◽  
Substituted Anilines ◽  
Reaction Sequence ◽  
Unsaturated Ketones ◽  
Direct Preparation

Adducts of dimethylamine and carbon dioxide form a "distillable ionic liquid" (DIMCARB) that may used as both a reaction medium and catalyst in the direct, atom-economical synthesis of useful synthetic building blocks, such as mono-condensed α,β-unsaturated ketones. The utilization of such building blocks in the synthesis of two new classes of versatile macrocycles, by a sequence of condensation reactions (H2O by-product), is described. Investigation into the mechanism of action of DIMCARB catalysis and observation of an aniline impurity arising from a competing reaction sequence led to development of a new multicomponent reaction for the direct preparation of 2- or 4-substituted anilines. Some of the macrocycles and anilines are, respectively, supramolecular host compounds and ligands for the preparation of metal complexes.

scholarly journals AgI /TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones

ChemPhysChem ◽  
2017 ◽  
Vol 18 (22) ◽  
pp. 3182-3188 ◽  
Author(s):  
Xue-Dong Li ◽  
Qing-Wen Song ◽  
Xian-Dong Lang ◽  
Yao Chang ◽  
Liang-Nian He
Keyword(s):  
Carbon Dioxide ◽  
Cascade Reaction ◽  
Propargyl Alcohols

scholarly journals Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones

2018 ◽  
Author(s):  
Shu-Mei Xia ◽  
Yu Song ◽  
Xue-Dong Li ◽  
Hong-Ru Li ◽  
Liang-Nian He
Keyword(s):  
Carbon Dioxide ◽  
Ionic Liquid ◽  
Reaction Time ◽  
Atmospheric Pressure ◽  
Liquid Structure ◽  
Domino Reaction ◽  
Protic Ionic Liquid ◽  
Three Component Reaction ◽  
Task Specific Ionic Liquid ◽  
Propargyl Alcohols

To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% [TBDH][TFE] (1,5,7-triazabicylo[4.4.0]dec-5-ene trifluoroethanol) was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2 pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 oC. This three-component reaction running under atmospheric pressure proves to be a clever detour to avoid the thermodynamic issue in the synthesis of 2-oxazolidinones starting from 2-aminoethanols and CO2.

Global and Local Reactivity Descriptors Based on Quadratic and Linear Energy Models for α,β-Unsaturated Organic Compounds

2018 ◽  
Author(s):  
Javier Oller ◽  
Patricia Perez ◽  
Paul W. Ayers ◽  
Esteban Vöhringer-Martinez
Keyword(s):  
Carbon Dioxide ◽  
Density Functional ◽  
Chemical Reactivity ◽  
Fukui Function ◽  
Nucleophilic Attack ◽  
Quadratic Model ◽  
Molecular Response ◽  
Local Descriptors ◽  
Unsaturated Ketones ◽  
Global And Local

<div>Global and local descriptors of chemical reactivity can be derived from conceptual density functional theory. Their explicit form, however, depends on how the energy is defined as a function of the number of electrons. Within the existing interpolation models, here, the quadratic and the linear energy model were used to derive global descriptors as the electrophilicity and nucleophilicity (defined as the negative of the ionization potential) and local descriptors employing either the corresponding condensed fukui function in the linear model or the local response of the global descriptor in the quadratic model. The ability of these descriptors to predict the reactivity of molecules with more than one reactive site was first studied on a set of α ,β -unsaturated ketones, where experimental rate constants for the nucleophilic attack is known. With the validated descriptors the reactivity of α ,β -unsaturated carboxylic compounds with different heteroatoms as α ,β -unsaturated thioesters, esters and amides as alternative substrates for the enzymatic CO<sub>2</sub> fixation studied experimentally by Erb <i>et al.</i> was addressed. The carbon dioxide fixation involves the reduction of the neutral α ,β -unsaturated carboxylic compounds by a nucleophilic attack of a hydride anion from NADPH and the following electrophilic attack by carbon dioxide. It was found that condensed values of the linear fukui function within the fragment of molecular response approximation describe best the reactivity of α ,β -unsaturated ketones. For the two relevant processes involved in CO<sub>2</sub> fixation the amides present the largest reactivity in vacuum and in aqueous solution compared to the esters and thioesters and may, therefore, serve as alternative sustrates of carboxylases.</div>

An iodine-promoted Meyer–Schuster rearrangement for the synthesis of α-iodo unsaturated ketones

2015 ◽  
Vol 2 (5) ◽  
pp. 506-509 ◽  
Author(s):  
Hai-Tao Zhu ◽  
Ming-Jin Fan ◽  
De-Suo Yang ◽  
Xiao-Ling Wang ◽  
Sen Ke ◽  
...  
Keyword(s):  
Unsaturated Ketones ◽  
Propargyl Alcohols

A facile and efficient iodine-promoted Meyer–Schuster rearrangement of propargyl alcohols for the synthesis of α-iodo-α,β-unsaturated ketones is presented.

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