A general and efficient synthesis of α-amino-α-aryl carbonitriles through the three-component reaction of arynes, aroyl cyanides, and DMF in a single step is described. DMF was not only used as the solvent, but it also participated in the reaction as a component. Used as the cyanide sources, the aroyl cyanides solved the toxicity and solubility problems associated with the use of HCN or metal cyanides in the Strecker synthesis. This procedure furnished α-amino-α-aryl carbonitriles in moderate to good yields with broad substrate scope. Moreover, this reaction could be performed under mild conditions with high atom economy.

Aryl nitriles were efficiently synthesized through copper-mediated cyanation of aryl halides using benzyl cyanide as the cyanide source. Aryl halides with various substituents on the aromatic ring afforded the corresponding aryl nitriles in 32–97 % yields (25 examples). This reaction could also be carried on a gram scale by using commercially available reagents. Additionally, a C–H bond oxidation and a C–CN cleavage are proposed to be involved in this cascade process.

9,11,12,14-Tetraaryldibenzo[f,h]imidazo[1,2-b]isoquinolines 3a–h were synthesized in moderate yields through the reaction of benzils with 1,3-diphenyl-2H-cyclopenta[l]phenanthren-2-ones and ammonium acetate. The photophysical properties of the products in solutions and in thin films were investigated, and strong emissions ranging from 492 to 516 nm were observed in cyclohexane solutions. Moreover, 3h exhibited potential as a versatile fluorescent chemosensor for the detection of solvent polarity, acidity, or trace amounts of nitroaromatics.

An efficient procedure for the synthesis of 2-aminoisoindolin-1-ones via a palladium-catalyzed three-component reaction of 2-halobenzaldehydes, hydrazines and carbon monoxide is reported. This cyclocarbonylation process can be performed smoothly under 1 atmospheric pressure of carbon monoxide to afford 2-aminoisoindolin-1-ones in moderate to excellent yields.

5 H-Benzo[b]carbazoles were prepared through a tandem reaction between 2-ethynyl-N-triphenylphosphoranylidene anilines and α-diazoketones through ketenimine intermediates in moderate-to-good yields. By using this approach, benzo[b]benzo[5,6]indolo[3,2-h]carbazoles, fluoreno[9,1-ab]carbazoles, and fluoreno[9,1-ab]fluoreno[1′,9′:5,6,7]indolo[3,2-h]carbazoles were constructed in one pot. Moreover, the resulting products emitted light within the range 410–521 nm, with quantum yields of up to 62 %.

Selective synthesis of functionalized naphthalenes and indenones by palladium-catalyzed cyclization of o-haloacetophenones and terminal alkynes in the presence of a secondary amine is reported. Under a nitrogen atmosphere, the palladium-catalyzed reaction of o-haloacetophenones with terminal alkynes in the presence of wet secondary aminesgenerated 1-(dialkylamino)-3-aryl/alkylnaphthalenes. When the reaction was conducted in air, 1-indenone-3-carbaldehydes were obtained. The synthesized β-arylnaphthalenes 4a–f emit light in a range from 386 to 452 nm with quantum yields from 0.10 to 0.48 in cyclohexane. The absorption and emission efficiency of 4d were finely tuned by the acidity of the environment, and this might be useful in the use of 4d as a fluorescent pH sensor.

By choosing DMF and dioxane as solvent, skeletons of indoles and pyrroles were constructed from alkynes and amines in the presence of PdCl₂, respectively. These Pd-catalyzed reactions were phosphane-free with high atom efficiency and could be conducted under mild basic conditions. The proposed mechanism for the selective formation of indoles and pyrroles in different solvents is also discussed in this paper.

Four different types of fused arenes, including fluoranthene, indeno[2,1-a]phenalene, (8H)cyclopenta[a]acenaphthylene, and pyridine[a]acenaphthylene, were efficiently constructed through iodine-mediated electrophilic cyclizations of 1,8-dialkynyl naphthalenes in a single step. Theoretical calculations supported our hypothesis that these reactions had high regioselectivity. Oxidative coupling of the fluoranthene skeleton, followed by aromatization, effectively synthesized perylene derivative 14, which emitted light at 597 nm in dichloromethane with an emission efficiency of 0.81 referred to 5,6,11,12-tetraphenylnaphthacene as a standard.

A copper-catalyzed one-pot synthesis of functionalized benzimidazoles has been developed. The procedure combines the copper-catalyzed three-component cascade reaction of sulfonyl azides, alkynes and 2-bromoaniline and the copper-catalyzed intramolecular N-arylation of sulfonamides in one sequence, which afforded the products in moderate to good yields.

An efficient synthesis of N-sulfonyl-substituted 2-imino-3,4-dihydrocoumarins and 2-iminocoumarins via a copper-catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and β-(ortho-hydroxyphenyl)-α,β-unsaturated ketones or ortho-hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.

A one-pot synthesis of N-sulfonyl-2-alkylidene-1,2,3,4-tetrahydropyrimidines via a highly selective and copper-catalyzed multicomponent reaction of sulfonyl azides, terminal alkynes and α,β-unsaturated imines has been developed. The α,β-unsaturated imine substrates could be generated from amines and α,β-unsaturated aldehydes in a one-pot process. The procedure is concise, general and efficient.

Two new star-shaped molecules 1 and 2 containing a triphenylamine/benzene moiety as the central core and three 2,4-dicyano-3-diethylamino-9,9-diethylfluorene moieties as the peripheral functional groups were synthesized and characterized. Charge transfer properties for these compounds were observed in photophysical experiments due to their D-A molecular structure. Compound 1 presented dual fluorescence in high polar solvents. Moreover, these compounds exhibited moderate fluorescence and high thermal stabilities, indicating their potential application to blue light emitting materials.