The N-arylsulfonamide group is an important moiety in medicinal chemistry because of its presence in many useful molecules with potential bioactivities. As a result, the development of synthetic routes to N-arylsulfonamides has been actively investigated. In recent years, the transition metal-catalyzed sulfonamidations of aryl halides, arylboronic acids and C_Ar-H bonds have extensively investigated, providing more efficient and environmentally friendly procedures for the synthesis of N-arylsulfonamides. The recent progress in the transition metal-catalyzed sulfonamidation reactions is reviewed. The aromatic substrates, transition metal-catalysts, ligands, sulfonamidating reagents, mechanisms of the sulfonamidation reactions are mainly discussed. Finally, the future development of them is also prospected.

Transition metal complexes-catalyzed homogeneous asymmetric hydrogenation is an important method for the synthesis of chiral compounds. At present, it is mainly focused on precious transition metal catalytic systems, such as ruthenium, rhodium, iridium and palladium. However, they are suffered from the difficulties of limited resource, high cost and environmental contamination. Therefore, it is important and necessary to develop catalytic systems based on cheap, non-toxic or low toxic, environmentally friendly and earth-abundant iron, cobalt, nickel, copper transition metal, which are in accordance with the requirements and research trend of the sustainable development of modern chemistry. The recent progress of nickel-catalyzed homogeneous asymmetric hydrogenation of prochiral unsaturated compounds containing carbon oxygen double bond (C=O), carbon carbon double bond (C=C) and carbon nitrogen double bond (C=N) is reviewed, and some breakthroughs and considerable research results achieved are introduced. In addition, the advantages and disadvantages of different types of substrates in nickel catalyst system are analyzed, and the future research direction is prospected.

The advent of visible light photoredox catalysis has transformed the way of single-electron transfer (SET) processes and accessing radical species. As a result, the chemistry of nitrogen-centered radicals has witnessed a remarkable gain in interest. Specifically, under visible light photoredox catalysis, iminyl radicals can be generated from oxime derivatives, such as O-acyl oximes, O-aryl oximes and α-imino-oxy acids. Meanwhile, the reactivity of iminyl radcials is investigated systematically. Iminyl radicals can undergo four major classes of reactions, namely addition to arenes, intramolecular hydrogen atom transfer and subsequent reactions, addition to alkenes, Norrish type-I fragmentation (cleavage of α-carbon-carbon bonds) and subsequent reactions. In this review, the most significant progresses in the use of oximes and their derivatives as iminyl precursors are discussed and their engagement in photoredox-mediated transformations is outlined.

Pure organic luminescent supramolecular materials with either phosphorescence or fluorescence emission have become a hot research topic due to their low toxity, facile preparation and wide applications. In recent years, our group has designed several novel luminescent macromolecules, achieving tunable multi-color emission. For the construction of phosphorescent materials, heavy atoms such as bromine and iodine as well as other hetroatoms with lone pair electrons like oxygen were employed to facilitate the intersystem crossing (ISC) process of the luminophores while rigid environments were provided via host-guest interactions and polymerization to restrict molecular motions, which results in reduced nonradiative decay. Moreover, noncovalent interactions are stimuli responsive because of their dynamic nature. Therefore, host-guest interactions, along with other noncovalent interactions including hydrophobic effects, π-π stacking and multiple hydrogen bonding, were also used for adjusting the intensities and wavelengths of phosphorescence or fluorescence, achieving diverse luminescence properties that the luminophore itself does not possess. This account summarizes the above advances and proposes possible directions for further research, like not only improving quantum yields but also expanding the range of emission wavelength of organic phosphorescent materials and developing luminescent materials that can intelligently respond to external stimuli.

In the past decades, transition metal-catalyzed C—H activation has experienced tremendous growth and revolutionized the field of organic synthesis. Several elegant strategies have been developed to promote reactivity and control precise site-selectivity. Among which, transient directing group strategy has been recognized to be an efficient and powerful approach for selective C—H functionalization. In contrast to traditional directing groups with covalent linkage, transient directing group strategy circumvents the covalent installation and removal of directing groups, which significantly improve the synthetic efficiency and broaden the range of synthetic applications. The recent advances in imine-based transition directing groups are summarized, providing an overview of recent achievements in this cutting-edge research field over the past few years. For clarity, it is classified into two sections according to the type of substrate and the type of activated hydrocarbon bond. Emphasis is placed on the fully discussion of various transient directing groups and their applications. Finally, the limitations of previous works and perspectives on this cutting-edge area are also described.

Driven by nowadays’ computing power, big data technology as well as learning algorithm, artificial intelligence (AI) has gained trenmendous attentions and become a transformative approach in many research areas. One of the most extensively explored AI approaches in chemistry is (deep) machine learning, which provides new twists in the fields of organic chemistry. The workflow of machine learning (ML) study in organic chemistry is briefly introduced. Meanwhile, the application of ML in the accurate prediction of chemical properties, molecular de novo design, chemical reaction prediction, retrosynthetic analysis and artificial intelligence synthetic machine are also summarized. In the end, the current challenges in this field are analyzed and discussed.

Development of efficient and practical asymmetric catalytic reactions plays a pivotal role for the concise syntheses of chiral drugs. Chiral ligands and catalysts are crucial for the selectivity and reactivity of the catalytic reactions. In this account, the design and development of a series of P-chiral mono- and bis-phosphorus ligands were summarized based on a benzooxaphosphane backbone and their applications in the synthesis of chiral drugs. Beside their P-chirality, these ligands are structurally rigid, sterically bulky, and electron-rich, providing good physical properties and tunabilities. Facilitated by these chiral ligands, a series of efficient and practical reactions including asymmetric hydrogenation, asymmetric cross-coupling, asymmetric cyclization, and asymmetric nucleophilic additions have been developed. The excellent conversions, yields, regioselectivities, enantioselectivities, and broad substrate scope have enabled concise and efficient syntheses of a series of chiral drugs.

Sulfur-containing heterocyclic compounds such as thiazole, thiophene, thiopyrone, widely exist in numerous natural products and biologically active molecules. Developing of effective strategies for the formation of sulfur-containing heterocycles has become a popular research hotspot. Meanwhile, the free-radical cascade reaction of unsaturated bonds in the synthesis of heterocycle has always been an important branch of synthetic chemistry, and the achieved progresses in recent years have also demonstrated its huge potential. Researchers found that sulfur atom could act as radical acceptors to build a C-S bond, and established a series of free radical reactions through this strategy. Among them, the radical cascade reactions of anisole derivatives have been gradually developed into an important synthetic tool toward sulfur-containing heterocycles. The recent advances in the field of radical-initiated reactions of anisoles for the construction of sulfur-containing heterocycles, in which sulfur atoms play as radical acceptors, are summarized. In addition, the reaction design, mechanism and applicability of sulfur-containing heterocyclic compounds via radical cyclization towards the synthesis of complex molecules are also covered.

Cinchona alkaloids widely exist in nature, which have attracted extensive interest of researchers because of their readily availability, biological activity, unique structural properties, and easy modification. With the development of asymmetric synthetic chemistry, cinchona alkaloids and their derivatives have been used as a privileged class of chiral catalysts or ligands in many catalytic asymmetric reactions. In particular, a variety of cinchona alkaloid-derived chiral catalysts and ligands have been developed and applied by organic chemists in catalytic asymmetric synthesis in rencent years. The recent progress made in this field over the past few years is summarized. Moreover, the related reaction mechanisms and future development prospects are also discussed.

Free radical reactions represent an efficient and significant tool to construct organic molecules by taking advantages of the high-efficiency, remarkable selectivity and good functional groups tolerance. Lewis-base boryl radicals are a class of species that possess unique structures and chemical reactivity, and a variety of synthetic applications have been developed. This account summarizes the research advances in this research field mainly contributed by our group. The results include Lewis-based boryl radicals enabled borylation reactions, Lewis-based boryl radicals-catalyzed new reactions, and Lewis-based boryl radicals promoted reduction reactions. These reactions feature mild reaction conditions, good functional groups compatibility, high yields, and excellent chemo-, regio-, and stereo-selectivities.

Thiocyanate, as a versatile synthon, which has important application value in many fields such as pharmaceutical, pesticide and materials. The photocatalytic and electrocatalytic thiocyanation reactions have been widely concerned in organic chemistry due to the advantages of green, efficiency and safety. In this review, the cross-coupling/thiocyanation reactions based on the photocatalytic and electrocatalytic are described, which is expected to be helpful in exploring the green synthesis of thiocyanates compounds.

By silica gel, Sephadex LH-20 column chromatography as well as preparative high performance liquid chromatography (HPLC), four previously undescribed α-pyrones sharing same primary structure were isolated from the brown rice solid medium of Fusarium tricinctum. Their structures were elucidated by spectroscopic analyses and their absolute configurations were finally confirmed by a modified Snatzke's method.

Climate change and depletion of fossil fuels have drawn considerable attention. Considering carbon dioxide is both the dominant greenhouse gas and renewable C₁ source, CO₂ valorization into valuable chemicals is considered to reconcile the environment benefit and sustainable chemistry development. Unfortunately, the thermodynamic stability and kinetic inertness of CO₂ make its chemical transformation challenging. As a consequence, developing highly efficient catalytic systems and synthetic protocols is crucial for CO₂ conversion. In recent years, He's group made great progress on strategy design and catalyst development for CO₂ conversion. A series novel CO₂ conversion strategies are proposed, including CO₂ capture and in-situ transformation, hierarchical reductive functionalization of CO₂, designing thermodynamically favorable reactions by multi-component cascade reaction and photo-promoted CO₂ transformation. Concurrently, the corresponding highly efficient catalytic systems were also developed based on the reaction mechanism and thus CO₂ transformation was successfully performed under mild conditions. It is hoped that this review can arouse broad concern on CO₂ transformation and spur its further development.

Fingerprint can directly identify the person, and it is one of the most important physical evidence in the criminal scene. Fingerprint has always been considered as the "head of physical evidence" and plays an important role in the investigation and court proceedings. However, the fingerprint on the relevant object can not be directly observed by human eyes in actual cases, so it is also called "latent fingerprint". Although the latent fingerprint development technology has made great progress, it still faces many difficulties in the aspects of nondestructive, sensitive and efficient. And, it will bring serious difficulties to the subsequent fingerprint identification work for the criminal technicians. Therefore, it is of great significance to develop highly selective, sensitive and convenient latent fingerprint developing materials or techniques. In view of this, on the basis of the research achievements at home and abroad, the application of traditional organic materials widely used in latent fingerprint development and the new fluorescent organic materials is briefly reviewed, such as aggregation induced emission materials, conjugated polymer materials and other organic fluorescent materials, in latent fingerprint development in recent ten years. The design concept of related organic materials and the mechanism of developing latent fingerprints are summarized. Finally, the existing problems are discussed, and the future development trend of organic materials in developing latent fingerprints is prospected.

Palladium-catalyzed organic transformations is an important branch of organometallic chemistry. Because it can efficiently construct carbon-carbon bonds and carbon-heteroatom bonds, palladium catalysis has been widely used in synthetic chemistry, material science and pharmaceutical industry. However, some of these reactions suffer from harsh reaction conditions, including high temperature and strong base. On the other hand, the visible-light photoredox catalysis employs the visible light as the energy source to generate highly reactive intermediates and realize many novel transformations, which are rare under the normal thermal reaction conditions, under mild reaction conditions. However, there are also limitations in reaction types and substrate scope in this field. In order to solve such problems in these two fields, organic chemists have merged the visible-light photoredox catalysis and palladium catalysis, realizing a series of novel organic transformations through the electron transfer or energy transfer between photosensitizer and organic palladium complex under mild conditions with high efficiency and selectivity, which has broad substrate scope and great application potential. In these transformations, visible-light photoredox catalysis and palladium catalysis both play their respective roles and cooperate well. The application of visible light photoredox and palladium dual catalysis in organic synthesis is summarized and the future research directions in this field are analyzed, which might help the further development of this field.

Chiral organosulfur compounds have a wide range of applications in the fields of medicinal chemistry and asymmetric synthesis. The development of new methods for the preparation of these compounds is an important task in organic synthetic chemistry. Enantioselective electrophilic thiolation of alkenes has emerged as a straightforward pathway for the synthesis of chiral sulfides. By this fashion, both the thio group and another valuable functional group can be introduced simultaneously into the parent alkene molecules. We designed and synthesized a series of chiral bifunctional chalcogenide catalysts and successfully applied them to intra- and inter-molecular enantioselective trifluoromethylthiolation, alkylthiolation, arylthiolation of different kinds of alkenes. A variety of chiral sulfides were obtained with high enantioselectivities. The recent advances in chiral bifunctional chalcogenide catalyzed enantioselective thiofunctionalization of alkenes developed by our group are summarized, and the prospect of this field is also discussed.

Catalytic asymmetric hydrofunctionalization of alkene is an important research field, which enables efficient construction of chiral molecules from readily available starting materials. Asymmetric hydrofunctionalization of multiple substituted alkenes represents a significant challenge to organic chemists because this process involves the simutaneous control of regio-, diastereo-, and enantio-selectivities. The key to solve this challenge is to identify novel catalyst systems to exert powerful regio- and stereo-control. Recently, by taking advantage of substrate-directed strategy, we have developed a number of alkene functionalization methods with excellent regio-, diastereo-, and enantio-selectivities. In particular, we focus on catalytic asymmetric hydroalkynylation of alkenes as a model transformation to analyze the factors that control the selectivity.

Industrial processes of fixing carbon dioxide (CO₂) lag far behind the carbon emission generated by human activity. Since CO₂ is an abundant, non-toxic, and cost-effective one carbon source, it is highly desirable to develop methodologies on converting CO₂ into valuable products for sustainable purpose. Based on the mechanistic insight of CO₂ activation by transition-metal catalyst and organocatalyst, a variety of efficient asymmetric CO₂ chemical fixation processes have been developed in recent years. This review discusses the advances of enantioselective synthesis of small molecules by asymmetric catalytic reactions with CO₂. The interaction between catalyst, CO₂ and substrate has been elaborated aiming to inspire the design of new catalytic systems for asymmetric CO₂ transformation.

Optically pure 1,3-amino alcohol is not only the important synthon in organic synthesis, but also the core structure of numerous bioactive molecule. As a result, the formation of 1,3-amino alcohols occupies a hot resarch topic in asymmetric synthesis. This review symmarizes several types of frequently-used methods and progress on synthesizing 1,3-amino alcohols:aldol or azo-aldol condensation synthesis, transition metal catalyzed C-H activation and amination synthesis, ring-opening and addition of azocyclic compounds, and[3+2] dipolar-cycloaddition reaction etc.

Due to its alkene moiety and highly strained aziridine scaffold, vinylaziridines represent a versatile type of synthetic building blocks and can undergo various chemcial transformations. These transformations enabled facile synthesis of a wide range of nitrogen-containing compounds, especially diverse nitrogen heterocycles, inculding azetidines, pyrrolidines, piperidines, azacycloheptanes and so on. Moreover, development of simple and efficient synthetic methods for various substituted vinylaziridines, stimulating their applications in the fields of organic synthesis, medicinal and agrochemistry, as well as fine chemistry. In recent years, such type of reagents continue to attract considerable research efforts from chemists and enjoyed rapid development. The representative examples of nucleophilic ring-opening and cyclization reactions of vinyl-aziridines over the past five years are summarized. Moreover, the prospects of further development are also disscussed.

In recent years, the field of organic fluorine chemistry has developed rapidly. Fluorination and fluorine-containing functionalization reactions have attracted extensive attention of organic chemists due to their special physical and chemical properties. The introduction of fluorine-containing group into drug molecules can improve the biological activity of drug molecules. Trifluoromethoxy group has strong electron absorption and high lipophilicity, compounds containing trifluoromethoxy play an important role in the fields of medicine, pesticides and materials. In recent years, some innovative strategies have been used to synthesize compounds containing trifluoromethoxy group. This account mainly focuses on the research of trifluoromethoxy reaction in our group, and some challenges faced by trifluoromethoxy reaction.

A series of thiazolo[3,2-a]pyrimidine derivatives were synthesized from the reaction of α-bromoacetophenone, aromatic aldehyde, malononitrile and thiourea which was catalyzed by Tröger's base derivative 5,12-dimethyl-3,10-diphenyl- bis-1H-pyrazol[b,f] [4,5]-1,5- diazadicyclo[3.3.1]-2,6-octadiene (1). The reaction mechanism was discussed by the ¹H NMR analysis and chemical experiments. The pharmacological activity results of the products indicated that most of products showed high inhibitory on one or more cancer cells in human hepatocarcinoma cell (HepG2), human non-small cell lung cancer cell (247) and human non-small cell lung cancer cell (A549) in vitro. And seven products have antibacterial activity against the methicillin-resistant Staphylococcus aureus. These results showed the great potential of these compounds in drug development.

Carbon dioxide is a readily available, low-cost, abundant, non-toxic C1 source, which can potentially serve as an ideal building block in synthetic chemistry. Recently, much progress, expecially multi-component reactions (MCRs) has been achieved in construction of carbonyl-containing heterocycles through annulation by using carbon dioxide as carbonyl/carboxyl source. Herein, the advances on the annulation reaction of atmospheric CO₂ with N-, and O-nucleophiles for the constructioin of various carbonyl-containing heterocycles, including benzoxazin, cyclic carbamates, lactams, oxazolidine-2,4-diones are reviewed. In addition, the carboxylation of C-nucleophiles with CO₂ toward carboxylic acids is also summarized.

Aggregation-induced emission (AIE) compounds have attracted much attention due to their important potential applications in biological and chemical sensing, luminescent materials, display and other areas. As an important class of functional molecules, organofluorine compounds have been widely studied in areas such as organic chemitry and materials chemistry. The organofluorine compounds with AIE properties are summarized and classified. The currently reported AIE organofluorine compounds include the fluorinated tetraphenylethene (TPE) derivatives, 9,10-distyrylanthracene (DSA) derivatives, cyanostilbene derivatives, distyrylbenzene derivatives, fluorinated polymers, carborane clusters, room temperature phosphorescent molecules, and some other fluorinated structures. With fluorine atoms in the structures, the stability of the resulting AIE compounds is generally improved, and fluorine atoms often participate in the intermolecular interactions leading to significant changes in the structure of the aggregation state, and hence changes in luminescence properties, for example, emission enhancement, bathochromism or hypsochromism of the emissions, improvement of the emission quantum yield and lifetime. The prospects of the future study are also discussed.

Versatile heterocyclic skeletons extensively exist in structures of natural products, drug molecules and organic materials, and have been synthesized through various strategies reported in literatures. Among them, the 1,3-dipolar cycloaddition is the most impressive class to build the related heterocycles. In the past, organic chemists generally employed[3+2] cycloaddition of 1,3-dipoles to assemble five-membered rings. As modern chemistry developes, researchers further turn their attention to the[3+3],[3+4],[3+5] and[3+6] cycloadditions, to construct six-, seven-, eight- and bridge-heterocyclic compounds. At present, review articles with topics on 1,3-dipolar cycloaddition mainly focus on[3+2] cycloaddition. Herein, A topic on[3+n] (n ≥ 3) cycloaddition of 1,3-dipoles, with comments on the developed methodologies is present and the outlook in this field is proposed.

The recent developments in asymmetric organotransition metal-catalyzed electrochemistry (AOMCE) are summarized. AOMCE processes can be divided into oxidative and reductive variants. In terms of oxidations, asymmetric functionalization of olefins, oxidative kinetic resolution of secondary alcohols or aldehydes, and asymmetric C—H functionalization reactions have been developed. Reductive processes discussed include asymmetric electrochemical carboxylation with carbon dioxide, asymmetric electrochemical decarboxylation, and asymmetric reductive coupling reactions. The combination of chiral ligands, transition-metal catalysts, and electrochemistry provides a novel angle by which to address the longstanding fundamental challenge of stereoinduction in traditional electrochemical organic synthesis.

Transition-metal catalyzed C-C bond cleavage reaction is one of the most challenge topics, and has drawn considerable attention in recent years. This process has not only emerged as a useful strategy for syntheses of complex molecular skeletons, but also satisfied atom economy. Compared to the noble transition metals catalysis such as Rh, Pd and Ir, the nickel catalysis offered a more cost effective option and exhibited unique activity or selectivity. This recent advances on the Ni-catalyzed C-C bond activations are summarized.

N-Methylation of amines and imines is one of the most important reactions for C-N bond formation. It is widely utilized for both laboratary research and industrial applications. Traditional methylation reactions involve the use of flammable, explosive and toxic starting materials. In contrast, newly developed methods have overcome this point and provide a mild strategy. In this transformation, C1 carbon source for the methyl group is important which determines the type of catalyst, reaction conditions and substrate scope. Herein, the research progress for the N-methylation of amines and imines is summarized based on different C1 carbon source.

Covalent organic frameworks (COFs) are an emerging class of porous crystalline organic materials connected by covalent bonds. Owing to their high crystallinity, low density, large surface area and designable structures, COFs have potential applications in molecular adsorption and separation, catalysis, optoelectronic devices, and energy storage. Recently, due to their inherent characteristics, COFs have attracted a lot of interests in sensing. The research progress of COFs in sensing, including explosive sensing, humidity sensing, metal ions sensing, pH sensing, biosensing and gas sensing is summarized. Finally, a perspective of the application of COFs in sensing is given.

In order to find efficient and low toxicity anti-tumor drugs, a series of novel 4-aminoquinazoline derivatives containing benzothiazole were designed and synthesized. And their antiproliferative activities against four human cancer cell lines[human breast cancer cell line (MCF-7), human gastric carcinoma cell line (MGC-803), human prostate cancer cell line (PC-3), human gastric carcinoma cell line (HGC-27)] were evaluated by using methyl thiazolyl tetrazolium (MTT) assay. The results showed that most compounds exhibited good antiproliferative activities against the four human tumor cell lines. Among them, 2-((benzo[d]thiazol-2-ylmethyl)thio)-N-(3-chloro-4-fluorophenyl)-quinazolin-4-amine (13n) showed the best antiproliferative activity against MCF-7, MGC 803, PC-3 and HGC-27 cancer cell lines, with IC₅₀ values of (6.01±0.54), (7.63±0.48), (6.16±0.34), (7.59±0.62) μmol·L^-1, respectively. Its activity was better than the positive control gefitinib. Molecular docking showed that compound 13n could bind well with epidermal growth factor receptor (EGFR). In a nutshell, this work provides clues to discover antitumor agent based on the quinazoline scaffold.

Organoboron compounds are valuable synthetic intermediates and widely used in the synthesis of medicine, pesticide and organic optoelectronic materials due to their extensive resouce and highly transformable ability. Among various organoboron compounds, the synthesis and transformation of alkylboron compounds have attracted much attention. As a sustainable and green energy, visible light shows an important effect in organic systhesis. Tetracoordinated alkylboron compounds could occur single electron transfer (SET) process to generate alkyl radical for further transformations. Herein, the recent advances in the photoinduced transformation of alkyl boron compounds are summarized.

Eight-membered carbocycles are widely found in natural products with significant biological activities and other molecules ranging from perfumes to potential materials. Therefore, accessing these eight-membered carbocycle embedded molecules is important for drug discovery, biological investigation, fragrance industry, material development and many other fields. However, the synthesis of eight-membered carbocycles is still posing challenges to synthetic chemists. Hence, tremendous efforts have been endeavored by many leading chemists to discover and develop new reactions in order to synthesize eight-membered carbocycles. Among these reactions, transition-metal-catalyzed cycloadditions of [m+n], [m+n+o], [m+ n+o+p] have evolved as powerful tools to achieve this aim. This topic has been reviewed in 2010. Summarized here are many new developments in this field and applications of the previously developed reactions in natural product synthesis since then.

Transition metal-catalyzed asymmetric oxidation, as one of important research targets of chiral synthesis, provides a direct, practical route for the synthesis of various chiral bioactive products and drugs, and has received much attention. The recent progress of the methods of transition metal-catalyzed asymmetric oxidation, especially, asymmetric oxidative functionalization of olefins, C-H bond asymmetric oxidation reaction, asymmetric BV oxidation and sulfide asymmetric oxidation is elaborated. Outlook of those issuesis is also discussed.

In recent years, decatungstate [W₁₀O₃₂]^4- as a catalyst has attracted much attention in the field of photocatalytic organic synthesis. With the catalysis of decatungstate, the C—H bond of substrate can be converted into the corresponding radical via a hydrogen atom transfer (HAT) progress under light irradiation. In this review, we summarized the recent advances of the application of decatungstate as a photocatalyst for the C—H functionalization to construct C—C, C—N, C—F bonds.

The CHF₂ moiety has been widely utilized in the design of pharmaceuticals and agrochemicals, because this group can act as hydrogen-bonding donor to improve the binding selectivity of biologically active compounds, as a bioisostere to substitute for methyl, methoxy, hydroxy, amino and thiol groups, and as a lipophilic regulator to improve the liposolubility of the active compounds. For example, 3-difluoromethylpyrazole scaffolds are present in many organic compounds that exhibit important biological activities. In this content, there are nearly ten kinds of pesticide molecules on the market that contain 3,4-disubstituted-3-(difluoromethyl)pyrazole units, with annual sales of up to one billion dollars. In this review, the methods of construction of 3,4-disubstituted 3-difluoromethylpyrazoles will been briefly summarized that have been reported so far. Four different strategies including using fluorinated reagents as substrates, difluoroacetic acid and its derivatives as fluorine building blocks, difluorodiazonium and others as fluorine building blocks will be introduced.

Repalcement of C=C bond with an isoeletronic and isosturctural B—N bond is an effective way to tune the photophyscial properties of polycylic aromatic hydrocarbons (PAHs), which have become the hot topic in the filed of optoelectronics. There are relatively smalll number of the non-planar BN-PAHs exsited, compared to the large number of planar BN-PAHs being synthesized. In this paper, the synthesis and properties of two series of non-planar BN[4]helicenes are discribed. The synthesis is quite straightforward by sequence of Suzuki cross coupling reaction, electrophilic borylation and nuleophilic substitution reactions. All of the target BN-[4]helicenes were characterized by ¹H NMR, ¹³C NMR and ¹¹B NMR. One of the BN-[4]helicene was also unmbigiously confired by X-ray crystal analysis, which showed the typical helically twisted geometries. Futhermore, the BC4N ring in the BN[4]helicene exhibited weak aromaticites, wihch were quantitified by experimental and theorectical calculations. Furthermore, both of the two series of BN[4]helicene showed significant redshift of their absorption spectra and slightly blueshift emission spectra comparing to the all-carbon [4]helicene analogue. Also, good fluorescence quantum yields range from 0.42 to 0.70 were obtained for the two series of BN[4]helicenes.

A highly selective and efficient copper-catalyzed sequential approach for the one-pot two-step synthesis of unsymmetrical 1,4-diamino-2-butynes from propiolic acid, secondary alkylamine, aldehyde and formaldehyde solution has been developed. The process of this reaction was involved in the generation of key intermediate propargylamines which were obtained via decarboxylative A³-coupling reaction. After that, the intermediate propargylamines would react with in situ formed iminium ions to give the cross-coupling target products in moderate to excellent yields under microwave irradiation.

As one of the most important click reactions, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) has found widespread applications. Nevertheless, the exploitation of enantioselective CuAAC remains largely undeveloped. Although the reaction itself does not generate chiral elements, the enantioselective CuAAC can be realized via the desymmetrization of prochiral dialkynes or diazides, as well as the kinetic resolution of racemic azides or terminal alkynes. Notably, enantioselective CuAAC provides efficient access to structurally diverse enantioenriched compounds featuring an azide, terminal alkyne or 1,4-disubstituted 1,2,3-triazoles, which are valuable structural units in organic synthesis or medicinal chemistry. Since the first highly enantioselective CuAAC reaction via desymmetrization of prochiral diynes was reported in 2013, substantial progress has been made in this research area. To date, enantioselective CuAAC has been successfully applied to the construction of central chirality, axial chirality and planar chirality. The recent exciting achievements are summarized, the challenges in this context are briefly discussed, and the synthetic opportunities for future development are outlined.

C-Glycosides are a class of carbohydrates with a variety of biological activities, and the construction of their unique C-C glycosidic bond is a hot and challenging topic in carbohydrate chemistry. The formation of new C-C bond from carbon-carbon double bond is a common strategy in organic chemistry. With the rapid development of ene-chemistry, great progress in the synthesis of C-glycosides from glycal donors containing 1,2-double bond has been made. In this review, the methods for the synthesis of C-glycosides based on glycals are summarized, including Ferrier I-type C-glycosylation, Heck-type C-glycosylation, C-glycosylation of 1-substituted glycals using transition metal-catalyzed coupling reaction, Michael-type C-glycosylation of 2-substituted glycals, and radical addition type C-glycosylation of glycals.