- Catalytic C–H Functionalization Methods
- Multicomponent Synthesis of Heterocycles
- Chemical Synthesis and Analysis
- Sulfur-Based Synthesis Techniques
- Synthesis and Catalytic Reactions
- Catalytic Alkyne Reactions
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Oxidative Organic Chemistry Reactions
- Fluorine in Organic Chemistry
- Radical Photochemical Reactions
- Synthesis and Biological Evaluation
- Catalytic Cross-Coupling Reactions
- Cyclopropane Reaction Mechanisms
- Synthetic Organic Chemistry Methods
- Advanced Synthetic Organic Chemistry
- Vanadium and Halogenation Chemistry
- Synthesis and pharmacology of benzodiazepine derivatives
- Radiopharmaceutical Chemistry and Applications
- Organophosphorus compounds synthesis
- Boron Compounds in Chemistry
- Chemical Synthesis and Reactions
- Organoboron and organosilicon chemistry
- Free Radicals and Antioxidants
- Conducting polymers and applications
Huizhou University
2018-2024
South China University of Technology
2011-2017
Guangzhou Experimental Station
2014
A new and efficient method for the synthesis of amides via palladium-catalyzed C−C coupling aryl halides with isocyanides is reported, by which a series were formed from readily available starting materials under mild conditions. This transformation could extend its use to natural products significant pharmaceuticals.
Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key the success this is formation a "bridging" palladium species, which can rearrange result in C-7 functionalization. ring-structure-dependent [2+2] cycloaddition cyclooctene has been achieved moderate good yields under similar conditions. Detailed facts importance specialist readers are published as "Supporting Information". Such...
A robust and regioselective palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides to the synthesis 4-halo-2-aminoquinolines is reported herein. The procedure constructs various moderate excellent yields (47–94%) broad substrates scope. Furthermore, this process can be easily extended 6H-indolo[2,3-b]quinolines via an intramolecular Buchwald–Hartwig cross-coupling reaction in two-step one-pot manner.
Abstract The difunctionalization of terminal alkynes was achieved with silver fluoride (AgF) and N ‐bromosuccinimide (NBS) as halogen sources. presence the halide moiety greatly enhances reactivity vinyl compounds that can probably be transformed into various products are difficult or even impossible to obtain via direct fluorination. Meanwhile, monofluoro<.>alkenes were facilely synthesized a highly chemo‐ regioselective fluorination electron‐deficient CC triple bonds using AgF...
A Pd-catalyzed aerobic oxidation of o-aminophenols and isocyanides for the synthesis 2-aminobenzoxazoles 3-aminobenzoxazines has been achieved in an air atmosphere. The procedure constructs with moderate to excellent yields a broad substrate scope. Apart from experimental simplicity, this methodology advantages mild reaction conditions easily accessible starting materials. Furthermore, utility method also successfully applied other types useful nitrogen heterocycles.
A clean and direct three-component radical 1,2-difunctionalization of various alkenes with perfluoroalkyl iodides thiosulfonates enabled by the electron donor–acceptor complex has been developed under light illumination at room temperature. The approach offers a convenient environmentally friendly route for simultaneous incorporation Csp3–Rf Csp3–S bonds, affording valuable polyfunctionalized alkane derivatives containing fluorine sulfur in satisfactory yields. Consequently, this methodology...
The palladium-catalyzed and CsF-promoted annulation reaction of bromoalkynes isocyanides regioselectively affords a diverse set 5-iminopyrrolone derivatives. This chemistry presumably proceeds through the bromoacrylamide intermediates, which can be readily prepared from nucleophilic addition to in presence CsF.
A robust route to 4-amine-benzo[b][1,4]oxazepines relying upon a palladium-catalyzed tandem reaction of o-aminophenols, bromoalkynes and isocyanides has been developed. This chemistry presumably proceeds through the migratory insertion into vinyl-palladium intermediate as key step.
A novel approach for the synthesis of polysubstituted 3-amino pyrroles via palladium-catalyzed three-component tandem reaction was developed. The procedure constructs various with moderate to excellent yields under mild conditions assembly efficiency, readily available starting materials, and good functional group tolerance. Furthermore, this process successfully applied different 3-phenyl-1,4-dihydropyrrolo[3,2-b]indole derivatives an intramolecular Buchwald–Hartwig cross-coupling in two steps.
An efficient aminoamidation and aminocyanation reaction of alkenes has been developed for the synthesis substituted indolines, tetrahydroisoquinolines pyrrolidines.
Abstract A palladium‐catalyzed, one‐pot cyclization reaction to construct (3 E )‐(imino)isoindolin‐1‐ones and )‐(imino)thiaisoindoline 1,1‐dioxides by introducing ortho ‐reactive functional groups on aryl halides is reported. Under optimal conditions, the afforded corresponding products in good excellent yields (up 93%) with high stereoselectivity. Notably, this transformation successfully extends its application for synthesis of phenanthridines dibenzooxazepines. This new synthetic protocol...
This protocol provides a unique and innovative approach to the construction of α-<italic>tert</italic>-butylperoxy-β-dichloromethyl alkanes, employing CHCl<sub>3</sub> as an alkylating reagent provide –CHCl<sub>2</sub> group, TBHP oxidant α-<sup>t</sup>BuOO group.
By using mono-<italic>N</italic>-protected amino acid (MPAA) ligand under Pd(<sc>ii</sc>) catalysis, regioselective C–H alkynylation of weak coordinated nitrogen functionalities was developed with great efficiency, proceeding<italic>via</italic>5, 6 and 7-membered palladacycle intermediates.
Abstract Carboranes, a three‐dimensional class of carbon‐boron molecular clusters with remarkable electronic, physical, chemical characteristics, have proved as useful building blocks in boron neutron capture therapy agents, supramolecular design, optoelectronics, nanomaterials and organometallic/coordination chemistry. Thus, various organic modifications the B−H C−H functionalities carboranes been developed. These methods great success utilize directing groups, such carboxylic acids, to...
A robust route to a diverse set of 6-aminophenanthridines <italic>via</italic> palladium-catalyzed C–H activation <italic>N</italic>-sulfonyl-2-aminobiaryl and isocyanide insertion is reported.
An efficient and convenient palladium-catalyzed cyclization reaction of alkynes with isocyanides is described herein. This protocol allows the practical synthesis many valuable polysubstituted maleimide derivatives after hydrolysis a broad scope substrates mild conditions. C–C, C═O, C–N bonds were constructed in this transformation isocyanide serving as both C N sources.
Gespannt ↔ flexibel: Die Palladium-katalysierte Reaktion von Halogenalkinen mit Norbornenderivaten erzeugt 7-Alkinylnorbornane (siehe Schema). Der Schlüssel zum Erfolg ist die Bildung einer „verbrückenden“ Palladiumspezies, unter Funktionalisierung an C-7 umlagern kann. der Ringstruktur abhängige [2+2]-Cycloaddition Cycloocten gelang vergleichbaren Reaktionsbedingungen guten Ausbeuten. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such...
An oxidative cascade that involves multicomponent reaction comprising a terminal alkyne, 2-amino N-heterocycle, benzyl or allylic bromide with molecular oxygen, delivering densely functionalized imidazo fused heterocycles, is described. This features cheap catalyst, green oxidant, and readily available starting materials, which make the overall synthesis applicable in quick access to relevant pharmaceutical molecules imidazole derived heterocycles.
A novel palladium-catalyzed cyclization of bromoacrylamides with isocyanides gives substituted 2,5-diimino-furans, which can be used as the precursor maleamides. This synthesis likely proceeds, after isonitrile insertion into C–Pd(II) bond, through coordination amide oxygen atom to Pd(II) centre a key step.
Abstract Regiodivergent [3+2] and [4+2] C−H annulation of imines imidate esters with unsymmetrical alkynes has been achieved under Rh(III) catalysis. Further transformation the aldehyde TMS functionality on indene products is also demonstrated. The current work highlights alcohols‐directed multiple esters, leading to diverse fused heterocycles.
The palladium-catalyzed C3-cyanation of indoles <italic>via</italic> direct C–H functionalization was achieved utilizing CH<sub>3</sub>CN as the cyanide source through transition-metal-catalyzed C–CN bond cleavage.