Huanfeng Jiang’s research while affiliated with China University of Mining and Technology and other places

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Publications (717)


Interfacial Electron Modulation of Ag x Cu y @ZIF-8 for Photothermally Catalyzing CO 2 Organic Transformations
  • Article

April 2025

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2 Reads

Inorganic Chemistry

Cheng Liu

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Yilei Cao

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Chaorong Qi

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[...]

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Yanwei Ren

Representative compounds containing butenolides and methods for the synthesis of butenolides with propargyl alcohols.
Substrate scope of propargyl alcohols. Reaction conditions: 1 (0.5 mmol), Pd(PCy3)2Cl2 (5 mol%), DMAP (2 eq), PhSiH3 (5 eq), m‐CF3C6H4COOH (2 eq), THF (dry, 2 mL), CO2 (2.5 MPa), 130 °C, 12 h. Isolated yields based on 1. [a] The reaction was conducted on a 1 mmol scale.
Synthetic applications of the butenolide 2 v. Reaction conditions: (a) 2 v (0.2 mmol), DBU (0.1 eq), MeNO2 (0.3 mL), room temperature, 10 h; (b) 2 v (0.2 mmol), Pd(OAc)2 (10 mol%), K2S2O8 (2 eq), TFA (2 mL), 90 °C, 1 h; (c) 2 v (0.2 mmol), NBS (1.1 eq), Pd(OAc)2 (10 mol%), K2S2O8 (2 eq), TfOH (2 eq), DCE (2 mL), 80 °C, 24 h; (d) 2 v (0.2 mmol), ethyl acrylate (4 eq), Pd(OAc)2 (10 mol%), K2S2O8 (2 eq), TFA (1.8 mL), TFAA (0.2 mL), 90 °C, 10 h.
Control experiments and proposed reaction mechanism.
Palladium‐Catalyzed Carbonylative Cyclization of Propargyl Alcohols with CO2: a Straightforward Route to Butenolides
  • Article
  • Publisher preview available

April 2025

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8 Reads

A palladium‐catalyzed carbonylative cyclization of propargyl alcohol with carbon dioxide (CO2) as a carbonyl source has been reported for the first time, which provides an efficient and straightforward route to a range of valuable butenolides in moderate to high yields. The reaction can be performed in one step and features good functional group tolerance and broad substrate scope. The application of the new method was also demonstrated by direct carbonylative cyclization of biologically active molecules.

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Tuning the electronic states of Pd(II) defect-engineered metal-organic framework catalysts for efficient conversion of isocyanides

April 2025

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10 Reads

Communications Chemistry

Recently, defective sites in MOFs have become an important tool for tuning the catalytic performance of MOFs. Herein, we report a heterogeneous catalyst “Pd-UiO-67(N)x” by utilizing the active site of defective MOF to modulate the electronic state of Pd, which demonstrates excellent catalytic performances in the oxidative cyclization reaction of isocyanides with o-aminophenols benefiting from the electron-deficient nature of the Pd species. When the Pd loading in defective Pd-UiO-67(N)x system was decreased to 0.37 mol %, the catalytic efficiency was significantly enhanced and the Pd turnover number (TON) increased to 232, which was 27 and 2.6 times higher than that of homogeneous Pd catalysts and defect-free Pd-UiO-67(N)0, respectively. The open pore structure of d-MOFs supports the adsorption of o-aminophenols. Additionally, the domain-limiting effect of the framework restricts the aggregation of Pd, resulting in good stability of the Pd species, which without significant loss of its activity in five consecutive reaction cycles. This work provides an insight into the improvement of stereoelectronic properties of organometallic catalysts through defect-engineered MOFs.





Photoredox‐Catalyzed Radical Alkylation/Cyclization of Isocyanides with Organoboron Reagents for Diversified Synthesis of N‐Heteroaromatics

The utility of alkyl boronic acids as alkyl radical precursors in photoredox‐catalyzed reactions has been limited due to their low reactivity. A photoredox‐catalyzed radical alkylation/cyclization of functional arylisocyanides with alkyl boronic acids is reported herein. This strategy allows the formation of alkyl radicals from boronic acids containing primary, secondary, and tertiary alkyl groups, which are subsequently transformed into structurally diverse alkylated products, including quinoxalines, phenanthridines, benzothiazoles, benzoselenazoles and quinolines. This transformation features readily available radical precursors and a broad substrate scope. The reaction mechanism is investigated by fluorescence quenching, light on/off, and cyclic voltammograms (CV) experiments. The combination of alkyl boronic acids with DBU may lead to the formation of the alkyl radical via a single electron transfer (SET) process, while the arylisocyanides may undergo an energy transfer (EnT) process with photocatalyst under visible light to generate the carbon radical or act as a radical acceptor to react with the alkyl radical.


Visible Light‐Induced Arylation/Alkylation/Phosphorylation of Isocyanides via EDA Complex Activation

March 2025

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6 Reads

Chinese Journal of Chemistry

Comprehensive Summary Herein, it is reported that the aryl radicals derived from aryl thianthrenium salts are used as coupling partner in the arylation reactions of isocyanides, simultaneously as initiators for the formation of alkyl and phosphoryl radicals from ethers and diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated and phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without the aid of metals or photocatalysts, exhibiting a wide substrate applicability and operational simplicity. Mechanistic studies suggest the involvement of radical processes and electron donor‐acceptor (EDA) complexes in this transformation.



Citations (24)


... This kinetic disparity rationalizes the experimentally o isolability of α-hydroxyphosphonates exclusively in aldehyde reactions, while ex the inherent predisposition of ketone substrates toward facile [1,2]-phospha-Bro rangement to directly yield α-phosphoryloxy esters. Recently, Wu's group [9] reported a palladium-catalyzed cyclization reactio aging [1,2]-phospha-Brook rearrangement to achieve base-modulated chemod synthesis of 2H-isoindole-1-carboxamide 4 and 2H-isoindole-1-carbonitrile 5 der ( Figure 4A). This methodology exhibits three hallmark characteristics: (i) dual iso incorporation, (ii) concurrent C-C/C-N bond formation, and (iii) ambient-tempera erability. ...

Reference:

Recent Developments in the [1,2]-Phospha-Brook Rearrangement Reaction
[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o ‐Bromobenzaldehydes: Access to 2 H ‐Isoindole‐1‐carboxamides and 2 H ‐Isoindole‐1‐carbonitriles
  • Citing Article
  • December 2024

Chinese Journal of Chemistry

... This approach was later extended by the research group in 2024 to produce isochromeno[4,3-c]quinolines 26 b from diarylalkynes 24 b and isocyanides 25 b by palladium-catalyzed tandem cyclization (Scheme 8c). [31] Optimal reaction conditions were 0.10 equivalent of Pd(PPh 3 ) 4 as the catalyst, 2.0 equivalents of Cu(OAc) 2 as the oxidant and 2.0 equivalent of HOAc as the additive in toluene at 90°C for 12 h. Monosubstituents that exerted different electronic effects at the C-5 or C-4 position on the substrates 24 b could proceed well, giving the corresponding products in moderate to good yields (30-74 %). ...

Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines
  • Citing Article
  • December 2024

The Journal of Organic Chemistry

... TYK2, a member of the Janus kinase (JAK) family, plays a crucial role in immune and hematopoietic cell functions, including cell growth, survival, differentiation, and immune response regulation [1]. Unlike JAK1, JAK2, and JAK3, TYK2 uniquely mediates intracellular signaling for key pro-inflammatory cytokines such as interleukin (IL)-12, IL-23, and type I interferons [2], which are central to the pathogenesis of psoriasis and other immune-mediated disorders. ...

Tyrosine Kinase 2 Inhibitors: Synthesis and Applications in the Treatment of Autoimmune Diseases
  • Citing Article
  • November 2024

European Journal of Medicinal Chemistry

... The isoxazole ring is one of the heterocyclic rings known for good therapeutic responses [8], and because of its pharmacological relevance, the biological profile of isoxazole derivatives has received a lot of research over the years. They have shown diverse biological profiles, including anticancer [9,10], antidiabetic [11], antioxidant [12], anti-Alzheimer's agents [13], anti-inflammatory [14], anticonvulsant [15], antihyperlipidemic [16], anti-tubulin [17], antimycobacterial [18], and other biological activities. Isoxazole consists of a five-membered ring comprising nitrogen and oxygen atoms. ...

Design, Synthesis and Antitumor Activity of 3,4,5-Trisubstituted Isoxazoles
  • Citing Article
  • August 2024

European Journal of Medicinal Chemistry Reports

... to the CDCl 3 solvent used in the 13 C NMR spectra [23]. The signals at 36 and 31 ppm may be attributed to the methyl groups present in the coordinated DMF solvent. ...

Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework

... [9] Heterogeneous catalysts have also been explored, though very limitedly studied regarding transition metal catalyzed isocyanide insertions. [10,11] In this respect, atomically dispersed metal catalysts, known as single-atom catalysts (SACs), [12][13][14] have attracted attention. However, the transition metals of these SACs can aggregate, which necessitates suitable support materials to stabilize them for effective catalytic use. ...

Enhanced Activity of MOF-Based Pd/Electron-Transfer Mediator Catalysts in Oxidation Reactions Involving Isonitrile by Defect Engineering
  • Citing Article
  • July 2024

ACS Catalysis

... [1,2] These heterocycles are part of the core of numerous natural products, pharmaceuticals, and agrochemicals, contributing to their pharmacological, chemical and physicalchemistry properties. [3][4][5] The presence of an oxygen atom in the ring system significantly influences the compound's reactivity, stability, and interaction with biological targets, making them indispensable in medicinal chemistry. [6][7][8] Within this context, isochromenes, an oxygencontaining bicyclic moiety (highlighted in blue in Figure 1), emerge as a particularly promising building block due to their versatile reactivity and potential for diverse functionalization. ...

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect
  • Citing Article
  • July 2024

Organic Process Research & Development

... 2-(Alkynylaryl)acetonitriles are a class of readily available, structurally diverse and bifunctional compounds with both cyano and alkyne groups used in the construction of important cyclic scaffolds such as naphthalenes, [15] azafluorenes, [16] benzocycloheptenes, [17] isoquinolines, [18] naphthyridines [19] and pyrroles. [20] Since the cyano group is a strong electron-withdrawing group, it can have an activating effect on the benzylic carbon. ...

Base-Promoted (5 + 2) Annulation between 2-(Alkynylaryl)acetonitriles and Arylalkynes for the Synthesis of Benzocycloheptene Derivatives
  • Citing Article
  • June 2024

Organic Letters

... Recently, Qi, Jiang and their team developed a straightforward method for synthesizing a variety of structurally intriguing and valuable 14-membered macrocyclic lactones [31]. This is achieved through a carboxylative macrocyclization of 3-triflyloxybenzynes with CO 2 and THF, while the novel [2 + 2 + 5 + 5] coupling reaction proceeds under transition metal-free conditions, forming one new C-C bond and three new C-O bonds in a single step ( Figure 11). ...

Macrocyclization of carbon dioxide with 3-triflyloxybenzynes and tetrahydrofuran: straightforward access to 14-membered macrolactones
  • Citing Article
  • June 2024

Chemical Communications

... Analytical samples were obtained by chromatography on silica gel using an EtOAc/petroleum ether or DCM/MeOH mixture as the eluent. 1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance 400 MHz NMR spectrometer (400 MHz for 1 H, 100 MHz for 13 C), Bruker Avance 500 MHz NMR spectrometer (500 MHz for 1 H, 125 MHz for 13 C). The chemical shifts were referenced using residual undeuterated solvent (CDCl 3 : δ 7.26, 77.0 ppm; DMSO-d 6 : δ 2.50, 39.52 ppm unless otherwise stated). ...

Asymmetric Total Synthesis of Alstrostine G Utilizing a Catalytic Asymmetric Desymmetrization Strategy