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We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids and aliphatic nitriles and exhibit good functional group compatibility and a high step economy. The reaction is scalable, and as-prepared products could be transformed into practical skeletons. Importantly, the late-stage derivatization of Momelotinib highlights the potential utility of this methodology.

The three-component tandem reaction of 2-aminobenzonitriles, arylboronic acids and ketones allowing the synthesis of polysubstitution quinolines is reported. This strategy presents a practical, efficient, one-pot procedure that delivers functional quinolines in moderate to good yields with high functional group tolerance. To enrich the synthetic applications in accessing diverse quinolines, a new method for the introduction of halogen substituents into target products has been developed as well, which shows potential for further synthetic elaborations.

An efficient and straightforward protocol for the assembly of the pharmaceutically and biologically valuable oxazole skeleton is achieved for the first time from readily available simple arenes and functionalized aliphatic nitriles. This transformation involves palladium-catalyzed C-H activation, carbopalladation and a tandem annulation sequence in one pot. Notably, the reaction proceeds efficiently under redox-neutral conditions, and exhibits high atom-economy. Deuterium-labeling experiments suggested that C-H bond cleavage of the simple arenes might be the rate-determining step.

Heterocycle-fused quinazolinone derivatives have attracted great attention due to their diversified biological and optical activities. In this study, a novel one-pot palladium-catalyzed cascade C–C coupling/cyclization/aromatization of 2-(4-oxoquinazolin-3(4H)-yl)acetonitrile derivatives with arylboronic acids has been disclosed to synthesize 1,3-diaryl-6H-pyrazino[2,1-b]quinazolin-6-one in water. This protocol provides an efficient access to valuable pyrazino-fused quinazolinones in a green solvent (i.e., water) with yields ranging from moderate to excellent. Furthermore, the photophysical properties of these molecules were investigated. The resultant pyrazino-fused quinazolinones exhibit tunable fluorescence, and 3e displays the aggregation induced emission properties with a large Stokes shift. This study provides a useful approach to the development of pyrazino-fused quinazolinones, which have potential applications in chemistry, biology, and materials science.

The homoleptic lanthanide complex Sm[N(TMS)2]3 is an efficient rare-earth catalyst for the hydroboration of alkynes to the corresponding alkenylboron compounds. Practical applications were demonstrated through a gram-scale synthesis and further transformations of an alkenylboron ester to a series of functional compounds. Isotopic labeling experiments, 1H NMR monitoring and kinetic studies were conducted to elucidate the reaction mechanism.

A novel palladium-catalyzed protocol for the synthesis of 9-arylacridines via tandem reaction of 2-(arylamino)benzonitrile with arylboronic acids in water has been developed with good functional group tolerance. The present synthetic route could be readily scaled up to gram quantity without difficulty. This methodology was further extended to the synthesis of a 4'-OH derivative, which showed estrogenic biological activity. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular Friedel-Crafts acylation and dehydration to acridines.

A palladium-catalyzed carbon-carbon bond activation-initiated reaction of 2-(3-phenyloxiran-2-yl)benzonitriles with arylboronic acids is reported. Multiple chemical bonds were cleavaged and reconstructed via β-carbon elimination in this reaction, enabling the construction of valuable benzo-fused dipyrromethenes that are difficult to prepare by other methods. Additionally, a series of benzannulated boron dipyrromethenes are synthesized and show practical significance in terms of expanding the applications and types of fluorescent materials. The proposed mechanism is supported by preliminary mechanistic experiments.

This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp

The efficient selective synthesis of furans and pyrroles has been realized by means of a palladium-catalyzed tandem addition/ring-opening/cyclization reaction of 2-(3-aryloxiran-2-yl)acetonitriles with arylboronic acids in aqueous medium for the first time. The chemoselectivity of this transformation can be predominantly governed by the steric effects of arylboronic acids: the reactions of 2-(3-aryloxiran-2-yl)acetonitriles with the less sterically hindered arylboronic acids provided furans as the sole products, while those of the sterically bulky arylboronic acids delivered pyrroles selectively. The 18O-labelled experiments revealed that the oxygen atom of furans is derived from water, and a plausible mechanism for this selective synthesis of furans and pyrroles was proposed.

We have demonstrated the first ever example of nickel complexes as effective catalysts to promote the C–C, N–C cascade coupling of ketonitriles with arylboronic acids, affording potentially biologically active 3-carboxylate-2,5-diaryl-pyrroles as well as 2,5-diarylpyrroles and 2,6-diarylpyridines. This protocol features a broad scope of substrates and excellent functional group tolerance, thus representing a highly versatile and atom-economical alternative to novel methods for the synthesis of various unsymmetrical diarylpyrroles and diarylpyridines under manageable conditions.

A Pd-catalyzed tandem reaction of 2-(cyanomethoxy)chalcones with thiophenes through direct C–H addition and sequential intramolecular conjugate addition/cyclization/aromatization provides a diverse range of 3-aryl-1-(thiophen-2-yl)benzofuro[2,3-c]pyridines. A representative product was assessed as a ratiometric fluorescent probe for Hg2+. This chemistry could also be applied to the synthesis of other fused ring systems.

A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.

A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring.

A palladium-catalyzed cascade reaction of 2′-acetyl-[1,1′-biphenyl]-2-carbonitriles with arylboronic acids is developed. This reaction affords a new class of seven-membered 5-arylidene-7-aryl-5H-di...

A novel metal-free one-pot protocol for the synthesis of potential biologically active molecules 3-selenylindoles via intramolecular cyclization/selenylation with simple 2-vinylaniline has been developed with moderate to good yield, thus representing it as a facile route to diverse substitution patterns around the indole core. The reaction proceeded smoothly with a broad substrate scope and excellent functional group tolerance. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Mechanistic studies have revealed that in situ formed selenium electrophile species may be the key intermediate for the selenocyclization process.

The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent se...

The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles with arylboronic acids in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines with good functional group tolerance under mild conditions. This chemistry has also been successfully applied to the synthesis of isoquinolones by the tandem reaction of methyl 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chemistry is also indicated by the synthesis of biologically active molecules.

Nitrogen doped Mg2TiO4 spinel, i.e. Mg2TiO4−xNy, has been synthesized and investigated as a photocatalyst for antibacterial activity. Mg2TiO4−xNy demonstrates superior photocatalytic activity for E. coli disinfection under visible light illumination (λ ≥ 400 nm). Complete disinfection of E. coli at a bacterial cell density of 1.0 × 107 CFU mL−1 can be achieved within merely 60 min. Mg2TiO4−xNy is capable of generating superoxide radicals ( O2−) under visible light illumination which are the reactive oxygen species (ROSs) for bacteria disinfection. DFT calculations have verified the importance of nitrogen dopants in improving the visible light sensitivity of Mg2TiO4−xNy. The facile synthesis, low cost, good biocompatibility and high disinfection activity of Mg2TiO4−xNy warrant promising applications in the field of water purification and antibacterial products.

The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.

Palladium-catalyzed base-free addition of aryltriolborates to aldehydes has been developed, leading to a wide range of carbinol derivatives in good to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The present synthetic route to carbinol derivatives could be readily scaled up to gram quantity without difficulty. Thus, this method represents a simple and practical procedure to access carbinol derivatives.

An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.

An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.