A5038469470- Catalytic C–H Functionalization Methods
- Cyclopropane Reaction Mechanisms
- Fluorine in Organic Chemistry
- Catalytic Cross-Coupling Reactions
- Synthesis and Catalytic Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Radical Photochemical Reactions
- Inorganic Fluorides and Related Compounds
- Crystallography and molecular interactions
- Catalytic Alkyne Reactions
- Oxidative Organic Chemistry Reactions
- Organoboron and organosilicon chemistry
- Molecular spectroscopy and chirality
- Click Chemistry and Applications
- Axial and Atropisomeric Chirality Synthesis
- Environmental Changes in China
- Chemical Synthesis and Reactions
- CO2 Reduction Techniques and Catalysts
- Chemical Synthesis and Analysis
- Asymmetric Hydrogenation and Catalysis
- Environmental and Agricultural Sciences
- Sulfur-Based Synthesis Techniques
- Epoxy Resin Curing Processes
- Ethnobotanical and Medicinal Plants Studies
Huazhong University of Science and Technology
2020-2024
Beijing Forestry University
2024
State Forestry and Grassland Administration
2024
National Yang Ming Chiao Tung University
2024
Xinjiang Institute of Materia Medica
2021
Universität Hamburg
2018-2019
Chinese Academy of Sciences
2010-2018
Peking University
2010-2018
Beijing National Laboratory for Molecular Sciences
2010-2018
Research Center for Eco-Environmental Sciences
2018
Cu-catalyzed cross-coupling of N-tosylhydrazones with 1,3-azoles leads to the direct C-H benzylation or allylation. Cu carbene migratory insertion is proposed play key role in this transformation.
Abstract A straightforward N‐trifluoroethylation of anilines has been developed based on silver‐catalyzed NH insertions with 2,2,2‐trifluorodiazoethane (CF 3 CHN 2 ). Mechanistically, the reaction is proposed to involve migratory insertion a silver carbene as key step. In contrast, when amides are employed substrates under similar conditions, O‐trifluoroethylation occurs afford trifluoroethyl imidates.
C–C Bond formation and β-F elimination have been achieved in a Cu(I)-catalyzed cross-coupling reaction of terminal alkynes trifluoromethyl ketone N-tosylhydrazones. The represents an efficient synthesis 1,1-difluoro-1,3-enyne derivatives. Mechanistically, the migratory insertion copper carbene intermediate leads to bond formation, which is followed by C–F cleavage.
The copper(I)-catalyzed alkylation of electron-deficient polyfluoroarenes with N-tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials is operationally simple, thus representing a practical method for the construction C(sp2)C(sp3) bonds through direct CH bond functionalization. Mechanistically, copper(I) carbene formation subsequent migratory insertion are proposed as key steps in pathway.
Abstract A strategy to introduce the SCF 3 group through Cu I ‐promoted reaction of diazo compounds with nucleophilic AgSCF trifluoromethylthiolation reagent was developed. Various were smoothly converted under mild conditions form C(sp )–SCF bond. Mechanistically, migratory insertion ‐bearing carbene intermediates is involved in this transformation.
Stereoselective additions of functionalized reagents to unsaturated hydrocarbons are attractive due the high atom economy, modularity and rapid generation complexity. We report a stereoselective cobalt-catalyzed (<italic>E</italic>)-halofluoroalkylation alkynes/alkenes that under mild conditions (2 mol% cat., 20 °C, acetone/water, 3 h). This reaction operates <italic>via</italic> radical chain mechanism involving terminal halogen transfer which obviates need for stoichiometric sacrificial reductant.
Abstract Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N ‐sulfonyl‐3‐arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6‐nucleophilic addition to p ‐quinone diimines. Control experiments suggest an ionic mechanism that differs from radical pathway commonly proposed for 1,6‐addition quinones. The origin selectivity investigated through computational studies. Preliminary studies...
Abstract Small molecules with conformationally rigid, three-dimensional geometry are highly desirable in drug development, toward which a direct, simple-to-complexity synthetic logic is still of considerable challenges. Here, we report intermolecular aza-[2 + 2] photocycloaddition (the aza-Paternò–Büchi reaction) indole that facilely assembles planar building blocks into ladder-shape azetidine-fused indoline pentacycles contiguous quaternary carbons, divergent head-to-head/head-to-tail...
Abstract The transition‐metal‐free 2,2,2‐trifluoroethylation and gem ‐difluorovinylation of arylboronic acids were developed. By employing different reaction conditions, these transformations provide both (2,2,2‐trifluoroethyl)arenes ‐difluorovinylarenes from 2,2,2‐trifluorodiazoethane. operation is simple scalable with good functional group tolerance.
Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case converting C(sp(3))-N bonds into C(sp(3))-C(sp(2)) bonds. conditions are mild, demonstrate good functional-group tolerance, can be scaled up.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTHalogenation with Copper(II). II. Unsaturated KetonesEdward M. Kosower and G.-S. WuCite this: J. Org. Chem. 1963, 28, 3, 633–638Publication Date (Print):March 1, 1963Publication History Published online1 May 2002Published inissue 1 March 1963https://pubs.acs.org/doi/10.1021/jo01038a008https://doi.org/10.1021/jo01038a008research-articleACS PublicationsRequest reuse permissionsArticle Views995Altmetric-Citations66LEARN ABOUT THESE METRICSArticle...
Abstract The copper(I)‐catalyzed three‐component reaction of N ‐tosylhydrazones, terminal alkynes and azides has been realized in an efficient regioselective manner. This constitutes a convenient method for the synthesis 1,4,5‐trisubstituted 1,2,3‐triazoles from simple starting substrates. Mechanistically, involves trapping copper(I) triazolide intermediate to form copper carbene subsequent migratory insertion protonation. magnified image
A highly versatile cobalt-catalyzed hydrosilylations of alkynes is reported. Near-perfect regiocontrol/stereocontrol was induced by the choice ligand: bidentate phosphines afforded (<italic>E</italic>)-β-vinylsilanes; α-vinylsilanes formed with bipyridine ligands.
Abstract Reported herein is an exceptional chemoselective ring‐opening/C(sp 3 )−C(sp ) bond formation in the copper(I)‐catalyzed reaction of cyclopropanols with diazo esters. The conventional O−H insertion product essentially suppressed by judicious choice conditions. DFT calculations provide insights into mechanism and rationale for this unusual chemoselectivity.
Abstract A palladium‐catalyzed oxygenative cross‐coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α‐disubstituted amide derivatives were obtained in good yields. Migratory insertion α‐oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step this reaction. The study demonstrates potential to serve precursors C−C bond‐forming reactions.
Pd(0)-catalyzed cross-coupling reactions of diazirines with aryl halides under microwave heating conditions afford a series substituted olefins. A reaction mechanism involving the migratory insertion Pd carbene intermediate is proposed.
Abstract A straightforward N‐trifluoroethylation of anilines has been developed based on silver‐catalyzed NH insertions with 2,2,2‐trifluorodiazoethane (CF 3 CHN 2 ). Mechanistically, the reaction is proposed to involve migratory insertion a silver carbene as key step. In contrast, when amides are employed substrates under similar conditions, O‐trifluoroethylation occurs afford trifluoroethyl imidates.
Comprehensive Summary The implementation of divergent protein engineering on the natural transaminase Vf ‐ω‐TA led to development two effective mutants (M2 and M8), enabling enzymatic synthesis chiral amine precursors Rivastigmine Apremilast, respectively. evolution enzymes was guided by crystal structures a focused mutagenesis strategy, allowing them effectively address challenging ketone substrates with significant steric hindrance. Under optimized reaction parameters, transamination...
A palladium-catalyzed cross-coupling reaction of electron-deficient aryl fluorides with <italic>N</italic>-tosylhydrazones, which involves C–F bond activation and migratory insertion palladium carbene, has been developed.
Abstract The copper(I)‐catalyzed alkylation of electron‐deficient polyfluoroarenes with N‐tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials is operationally simple, thus representing a practical method for the construction C(sp 2 )C(sp 3 ) bonds through direct CH bond functionalization. Mechanistically, copper(I) carbene formation subsequent migratory insertion are proposed as key steps in pathway.