A5055508803- Catalytic C–H Functionalization Methods
- Fluorine in Organic Chemistry
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Synthesis and Catalytic Reactions
- Oxidative Organic Chemistry Reactions
- Radical Photochemical Reactions
- Catalytic Cross-Coupling Reactions
- Inorganic Fluorides and Related Compounds
- Sulfur-Based Synthesis Techniques
- Asymmetric Hydrogenation and Catalysis
- Cyclopropane Reaction Mechanisms
- Crystallography and molecular interactions
- Catalytic Alkyne Reactions
- Synthetic Organic Chemistry Methods
- Asymmetric Synthesis and Catalysis
- Chemical Synthesis and Analysis
- Carbon dioxide utilization in catalysis
- Vanadium and Halogenation Chemistry
- Flame retardant materials and properties
- Chemical Synthesis and Reactions
- Synthesis and Reactions of Organic Compounds
- Metal-Catalyzed Oxygenation Mechanisms
- Enzyme-mediated dye degradation
- Chinese history and philosophy
Shanghai Institute of Organic Chemistry
2016-2025
Chinese Academy of Sciences
2015-2025
Chinese Academy of Medical Sciences & Peking Union Medical College
2021-2025
University of Science and Technology of China
2018-2024
University of Chinese Academy of Sciences
2016-2024
East China Normal University
2019-2024
Florida State University
2024
Beijing Forestry University
2023-2024
Jilin University
2024
Johns Hopkins University
2005-2023
Aortic aneurysm and dissection are manifestations of Marfan syndrome (MFS), a disorder caused by mutations in the gene that encodes fibrillin-1. Selected MFS reflect excessive signaling transforming growth factor-beta (TGF-beta) family cytokines. We show aortic mouse model is associated with increased TGF-beta can be prevented antagonists such as TGF-beta-neutralizing antibody or angiotensin II type 1 receptor (AT1) blocker, losartan. AT1 antagonism also partially reversed noncardiovascular...
ConspectusDifunctionalization of alkenes to incorporate two functional groups across a double bond has emerged as powerful transformation greatly increase molecular complexity in organic synthesis with improved efficiency. Historically, palladium-catalyzed difunctionalization suffered from difficulties introducing second group through reductive elimination Pd(II) intermediate and competing β-hydride reactions. To overcome these challenges, one strategy involves utilizing steric bulky ligand...
Direct methods for stereoselective functionalization of sp 3 -hybridized carbon–hydrogen [C(sp )–H] bonds in complex organic molecules could facilitate much more efficient preparation therapeutics and agrochemicals. Here, we report a copper-catalyzed radical relay pathway enantioselective conversion benzylic C–H into nitriles. Hydrogen-atom abstraction affords an achiral that undergoes asymmetric C(sp )–CN bond formation upon reaction with chiral copper catalyst. The reactions proceed...
ConspectusThe direct transformation of C–H bonds into diverse functional groups represents one the most atom- and step-economical strategies for organic synthesis has received substantial attention over last few decades. Despite recent advances, asymmetric bond functionalizations are less developed, especially oxidations sp3 bonds. Inspired by enzyme (e.g., P450) catalysis, chemists have made great efforts to develop non-enzymatic systems enantioselective However, involvement highly reactive...
A palladium-catalyzed intramolecular oxidative aryltrifluoromethylation reaction of activated alkenes has been explored. The allows for an efficient synthesis a variety CF3-containing oxindoles. Preliminary mechanistic study indicated that the involves Csp3–PdIV(CF3) intermediate, which undergoes reductive elimination to afford Csp3–CF3 bond.
Synthetic methods that achieve oxidative 1,2-difunctionalization of alkenes are very powerful in organic chemistry. Here we report the first examples intermolecular Pd-catalyzed aminoacetoxylation with phthalimide as nitrogen source and PhI(OAc)2 stoichiometric oxidant acetate. These reactions highly regio- diastereoselective, mechanistic studies reveal reaction proceeds via cis-aminopalladation alkene followed by cleavage intermediate Pd−C bond inversion stereochemistry.
Abstract A novel copper‐catalyzed intermolecular trifluoromethylazidation of alkenes has been developed under mild reaction conditions. variety CF 3 ‐containing organoazides were directly synthesized from a wide range olefins, including activated and unactivated alkenes, the resulting products can be easily transformed into corresponding amine derivatives.
A novel palladium-catalyzed intramolecular oxidative aminofluorination of unactivated alkenes has been developed, in which AgF was used as a key fluorinating reagent and PhI(OPiv)2 oxidant. The reaction afforded vicinal fluoroamine products with very high regioselectivity. Pd(II/IV) catalytic cycle proposed, preliminary mechanistic studies indicated that direct reductive elimination Pd(IV) intermediates is favored, albeit competing SN2 nucleophilic attack by fluorine, to form C−F bond.
Not one but two: The title reaction proceeds through the dual CH bond cleavage of both aniline and acetonitrile (see scheme). affords a variety cyano-bearing indolinones in excellent yield. Mechanistic studies demonstrate that this involves fast arylation olefin rate-determining activation acetonitrile. Detailed facts importance to specialist readers are published as "Supporting Information". Such documents peer-reviewed, not copy-edited or typeset. They made available submitted by authors....
A novel enantioselective copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes has been developed, in which a variety CF3-containing alkylnitriles are furnished with excellent enantiomeric excess. Preliminary mechanistic studies revealed (1) the reaction was initiated by SET process between activated Togni's CF3+ reagent and Cu(I) catalyst; (2) released CF3 radical readily added to styrene provide benzylic radical, then trapped chiral Cu(II) cyanide species deliver desired...
A novel palladium-catalyzed intermolecular aminofluorination of styrenes, with N-fluorobenzenesulfonimide (NFSI) functioning not only as a fluorinating reagent but also an aminating reagent, has been developed. The reaction afforded vicinal fluoroamine products very high regioselectivity. This transformation may involve fluoropalladation styrene key step for C−F bond formation. bidental nitrogen ligand is crucial to achieving the successfully.
The merger of photoredox catalysis with asymmetric copper have been realized to convert achiral carboxylic acids into enantiomerically enriched alkyl nitriles. Under mild reaction conditions, the exhibits broad substrate scope, high yields and enantioselectivities. Furthermore, can be scaled up synthesize key chiral intermediates bioactive compounds.
A novel copper-catalyzed intermolecular trifluoromethylarylation of alkenes is developed using less active ether-type Togni's reagent under mild reaction conditions. Various and diverse arylboronic acids are compatible with these Preliminary mechanistic studies reveal that a mutual activation process between acid CF3+ essential. In addition, the might involve rate-determining transmetalation, final aryl C–C bond derived from reductive elimination aryl(alkyl)Cu(III) intermediate.
A novel asymmetric radical trifluoromethyl-arylation of alkenes has been developed, which provides an efficient approach to access chiral CF3-containing 1,1-diarylmethane derivatives with good excellent enantioselectivity. Various vinyl arenes and aryl boronic acids are compatible these conditions. The utility the method is demonstrated by accessing modified bioactive molecules.
We have developed a copper-catalyzed enantioselective intermolecular aminoarylation of alkenes using novel N-fluoro-N-alkylsulfonamide as the amine reagent, which could react with Cu(I) catalyst to release related amino radical. After addition styrene, generated benzylic radical couple chiral L*CuIIAr complex achieve arylation. Various optical 2,2-diarylethylamines were efficiently synthesized from simple styrenes high enantioselectivity, and these products can serve valuable synthons toward...
Abstract Asymmetric copper‐catalyzed intermolecular amino‐ and azidocyanation reactions of alkenes have been developed that proceed via a radical process in which key benzylic intermediate is enantioselectively trapped by chiral Box/Cu II cyanide complex. A variety enantiomerically enriched β‐amino/azido alkylnitriles were efficiently synthesized. The β‐azido could be converted into series highly valuable optically active amine‐based building blocks bioactive compounds.
Classic methods for the synthesis of allenes usually introduce only one functional group into products. In this review, we highlight recent advances and perspectives in by transition metal‐catalyzed 1,4‐functionalization unactivated 1,3‐enynes.
In comparison to the traditional petroleum-based plastics, polylactic acid, most popular biodegradable plastic, can be decomposed into carbon dioxide and water in environment. However, natural degradation of acid requires a substantial period time and, more importantly, it is carbon-emitting process. Therefore, highly desirable develop novel transformation process that upcycle plastic trash value-added products, especially with high chemical selectivity. Here we demonstrate one-pot catalytic...
The first enantioselective radical trifluoromethylation of benzylic C–H bonds has been established by a cooperative photoredox and copper catalysis system, providing straightforward access to structurally diverse products in good yields with excellent enantioselectivities under mild conditions. Our method features broad substrate scope functional group compatibility. Merging the is essential for reaction, where used generation radicals from alkyl arenes through hydrogen atom transfer process...
Asymmetric sp3 C–H functionalization has been demonstrated to substantially expedite target molecule synthesis, spanning from feedstocks upgradation late-stage modification of complex molecules. Herein, we report a highly efficient and sustainable method for enantioselective benzylic cyanation by merging electrophoto- copper catalysis. A novel catalytic system allows one independently regulate the hydrogen atom transfer step radical formation speciation Cu(II)/Cu(I) effectively capture...