scholarly journals Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2260
Author(s):  
Margherita Pirola ◽  
Alessandra Puglisi ◽  
Laura Raimondi ◽  
Alessandra Forni ◽  
Maurizio Benaglia
Keyword(s):  
Continuous Flow ◽  
Stereoselective Synthesis ◽  
Catalytic Reduction ◽  
Lewis Base ◽  
Crucial Point ◽  
X Ray ◽  
Metal Free ◽  
Target Molecule ◽  
Synthetic Strategy ◽  
Synthetic Sequence

A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the catalytic reduction of a fluorinated enamine with trichlorosilane as reducing agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation of the target chiral fluorinated amine in up to an 87:13 diastereoisomeric ratio.

Transition-metal-free catalytic hydroboration reduction of amides to amines

2020 ◽  
Vol 7 (21) ◽  
pp. 3515-3520
Author(s):  
Wubing Yao ◽  
Jiali Wang ◽  
Aiguo Zhong ◽  
Shiliang Wang ◽  
Yinlin Shao
Keyword(s):  
Transition Metal ◽  
Selective Catalytic Reduction ◽  
Catalytic Reduction ◽  
Value Added ◽  
Metal Free

The selective catalytic reduction of amides to value-added amine products is a desirable but challenging transformation.

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives Through a Combination of 8-Aminoquinoline Directed C–H Arylations and Transamidations

2019 ◽  
Author(s):  
Michael Oschmann ◽  
Linus Johansson Holm ◽  
Oscar Verho
Keyword(s):  
Small Molecule ◽  
High Efficiency ◽  
Synthetic Strategy ◽  
Small Molecule Screening ◽  
Physiological Properties ◽  
Wide Range ◽  
Directing Group ◽  
Synthetic Sequence

Benzofurans are everywhere in nature and they have been extensively studied by medicinal chemists over the years because of their chemotherapeutic and physiological properties. Herein, we describe a strategy that can be used to access elaborate benzo-2-carboxamide derivatives, which involves a synthetic sequence of 8-aminoquinoline directed C–H arylations followed by transamidations. For the directed C–H arylations, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a two-step transamidation protocol. By bocylating the 8-aminoquinoline amide moiety of these products, it proved possible to activate them towards aminolysis with different amine nucleophiles. Interestingly, this aminolysis reaction was found to proceed efficiently without the need of any additional catalyst or additive. Given the high efficiency and modularity of this synthetic strategy, it constitute a very attractive approach for generating structurally-diverse collections of benzofuran derivatives for small molecule screening.

Evaluation of Different Synthetic Routes to (2R,3R)-3-Hydroxymethyl-2-(4-hydroxy- 3-methoxyphenyl)-1,4-Benzodioxane-6-Carbaldehyde

2020 ◽  
Vol 23 (26) ◽  
pp. 2960-2968
Author(s):  
Renáta Kertiné Ferenczi ◽  
Tünde-Zita Illyés ◽  
Sándor Balázs Király ◽  
Gyula Hoffka ◽  
László Szilágyi ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Stereoselective Synthesis ◽  
Cotton Effect ◽  
Enantioselective Synthesis ◽  
Aryl Group ◽  
Target Molecule ◽  
Synthetic Routes ◽  
The Absolute

The reported enantioselective synthesis for the preparation of (+)-(2R,3R)-2-(4- hydroxy-3-methoxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-carbaldehyde, precursor for the stereoselective synthesis of bioactive flavanolignans, could not be reproduced. Thus, the target molecule was prepared via the synthesis and separation of diastereomeric O-glucosides. TDDFT-ECD calculations and the 1,4-benzodioxane helicity rule were utilized to determine the absolute configuration. ECD calculations also confirmed that the 1Lb Cotton effect is governed by the helicity of the heteroring, while the higher-energy ECD transitions reflect mainly the orientation of the equatorial C-2 aryl group.

scholarly journals Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Peng-Ying Jiang ◽  
Kai-Fang Fan ◽  
Shaoyu Li ◽  
Shao-Hua Xiang ◽  
Bin Tan
Keyword(s):  
Asymmetric Catalysis ◽  
Kinetic Resolution ◽  
Academic Research ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Industrial Applications ◽  
Lewis Base ◽  
Production Costs ◽  
Metal Free ◽  
Base Catalysts

AbstractAs an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.

Selective catalytic reduction of NO by Co-Mn based nanocatalysts

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Vahid Zabihi ◽  
Mohammad Hasan Eikani ◽  
Mehdi Ardjmand ◽  
Seyed Mahdi Latifi ◽  
Alireza Salehirad
Keyword(s):  
Selective Catalytic Reduction ◽  
Catalytic Reduction ◽  
Energy Dispersive ◽  
Diffraction Field ◽  
X Ray Diffraction ◽  
X Ray ◽  
Analysis Techniques ◽  
Acidic Sites ◽  
Temperature Window ◽  
Temperature Programmed

Abstract One of the most significant aspects in selective catalytic reduction (SCR) of nitrogen oxides (NOx) is developing suitable catalysts by which the process occurs in a favorable way. At the present work SCR reaction by ammonia (NH3-SCR) was conducted using Co-Mn spinel and its composite with Fe-Mn spinel, as nanocatalysts. The nanocatalysts were fabricated through liquid routes and then their physicochemical properties such as phase composition, degree of agglomeration, particle size distribution, specific surface area and also surface acidic sites have been investigated by X-ray diffraction, Field Emission Scanning Electron Microscope, Energy-dispersive X-ray spectroscopy, energy dispersive spectroscopy mapping, Brunauer–Emmett–Teller, temperature-programmed reduction (H2-TPR) and temperature-programmed desorption of ammonia (NH3-TPD) analysis techniques. The catalytic activity tests in a temperature window of 150–400 °C and gas hourly space velocities of 10,000, 18,000 and 30,000 h−1 revealed that almost in all studied conditions, CoMn2O4/FeMn2O4 nanocomposite exhibited better performance in SCR reaction than CoMn2O4 spinel.

scholarly journals Effects of thermal treatments on characteristics and morphological variations in the deposits of urea-SCR systems

2021 ◽  
Author(s):  
Sadashiva Prabhu S ◽  
Kapilan Natesan ◽  
Nagaraj Shivappa Nayak
Keyword(s):  
Cyanuric Acid ◽  
Catalytic Reduction ◽  
Morphological Changes ◽  
Water Solution ◽  
Slight Variation ◽  
Gravimetric Analysis ◽  
Oxides Of Nitrogen ◽  
Deposit Formation ◽  
X Ray ◽  
Exhaust Gases

AbstractSelective catalytic reduction (SCR) systems are employed by automobile manufacturers for the abatement of environmental pollutants like oxides of nitrogen (NOx) emitted from exhaust gases of diesel engines. In SCR, the urea-water solution (UWS) is injected to exhaust gases in the form of a spray to generate the reducing agent NH3. Deposit formation at lower temperatures is a major concern with this technology. The deposits not only create backpressure but also leak NH3 to the environment as they deplete. It is very important to know the depletion characteristics of deposits formed at lower temperatures in order to assess the NH3 leakage to the environment when the engine exhaust gases attain higher temperatures. In the present work, deposits formed at a low-temperature range of 150–200°C for continuous run along with UWS injection were investigated. Additionally, they were aged at 300°C in the absence of UWS to check the variation in characteristics with the rise of temperature. By gravimetric analysis, it is inferred that the deposits formed at higher pre-age temperatures are less prone to depletion as the temperature increases. The elemental analysis using energy-dispersive X-ray spectroscopy (EDX) indicates slight variation in carbon, nitrogen and oxygen compositions for all the pre-age conditions. As an extended study, the byproducts at pre-age and post-age conditions were investigated through X-ray diffraction (XRD). The compounds like cyanuric acid (CYA) and biuret were not observed when pre-age samples were aged at 300°C. Instead, the compounds like ammelide, ammeline, triuret and melamine were observed. Scanning electron microscope (SEM) study revealed morphological changes in both pre-age and post-age samples. Further, the crystallinity variations were also observed for the changes in the heating cycles during deposit formation. The gravimetric analysis of deposits in pre-age and post-age conditions helps in predicting the amount of deposits for transient load cycles.

The use of main-group elements to mimic catalytic behavior of transition metals I: reduction of dinitrogen to ammonia catalyzed by bis(Lewis base)borylenium diradicals

2020 ◽  
Vol 22 (48) ◽  
pp. 28423-28433
Author(s):  
Yu Wang ◽  
Chun-Guang Liu
Keyword(s):  
Transition Metals ◽  
Main Group ◽  
Lewis Base ◽  
Main Group Elements ◽  
Catalytic Behavior ◽  
Metal Free

An emerging class of compounds, bis(Lewis base)borylenium diradicals with an electron-rich boron(i) center, are potential metal-free catalysts for dinitrogen activation and reduction.

One-pot synthesis of bio-based polycarbonates from dimethyl carbonate and isosorbide under metal-free condition

2020 ◽  
Vol 22 (14) ◽  
pp. 4550-4560
Author(s):  
Wenjuan Fang ◽  
Zhencai Zhang ◽  
Zifeng Yang ◽  
Yaqin Zhang ◽  
Fei Xu ◽  
...  
Keyword(s):  
Dimethyl Carbonate ◽  
One Pot ◽  
Free Condition ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Synthetic Strategy

A synthetic strategy for bio-based polycarbonate was developed via one-pot polymerization of renewable monomer isosorbide and dimethyl carbonate using eco-friendly organo-catalysts.

Sign in / Sign up

Export Citation Format

Share Document