Pd(OAc)2-catalyzed direct C–H arylation of an arene triazole template has been explored using the triazole ring as a directing group. The N(3)-ortho C–H bond on C(4) aryl of 1,4-disubstituted 1,2,3-triazoles can be selectively arylated, exclusively affording the expected structures. The diarylated products could be selectively formed when the triazole derivative beared a para substituent on C(4) aryl of the heterocycle, while the monoarylated target molecules resulted from substrates with an ortho or meta substituent.

CuI-catalyzed selective Ullmann C–O coupling of 1,4-disubstituted 1,2,3-triazole bromides with phenols were achieved through the coordination of N(2) atom. The ortho C–Br bond in N(1) aryl can be selectively coupled with phenols, while other C–Br bonds remain inert, generating ortho aryloxyl 1,4-diaryl 1,2,3-triazoles.

A concise and efficient method for the synthesis of etherified 3-(1H-1,2,3-triazol-1-yl)phenyl iodides from 1,4-disubstituted 1,2,3-triazoles under metal-free conditions has been developed. In the presence of ArI(OAc)2, a range of 1,2,3-triazole substrates that contain a hydroxy group underwent a direct O–H arylation and C–H iodination to afford functionalized 1,2,3-triazoles in good to excellent yields.

A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes in moderate to excellent yields under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.

•Non-fluorescent Fe3O4–CuFL–RBS nanocomposites were facilely prepared by electrostatic interactions.•The nanocomposites enabled releasing NO upon visible light irradiation.•The released NO could be detected in situ based on selective fluorescence turn-on response of nanocomposites to NO.Under electrostatic interactions, polyethylenimine-stabilized Fe3O4 magnetic nanoparticles were assembled with photosensitive nitric oxide (NO) donors (Fe4S3(NO7−))(Fe4S3(NO7−)), RBS) and CuFL complex consisting of fluorescein derivatives (FL) and CuII to prepare Fe3O4–CuFL–RBS nanocomposites. The as-prepared nanocomposites exhibited weak fluorescence and hardly any release of NO upon light irradiation of 480 nm. The nanocomposites enabled NO release due to RBS photolysis under 365 nm light irradiation, while the released NO could in situ conjugate with CuFL to form FL–NO complex based on N-nitrosate reaction, which was verified by fluorescence increase responses of FL–NO (excited at 480 nm). Thus, Fe3O4–CuFL–RBS nanocomposites realized light-triggered NO release and turn-on fluorescence detection of NO in situ.

The synthesis of aryl azides was achieved in one-pot from aromatic nitrocompounds with yields ranging from good to excellent under mild conditions. The conditions were found to be successful for nitrobenzenes with various functionalities with high efficiency.

A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions. The reactions can be smoothly completed within a total 10 min through a two-step procedure, including copper-catalyzed coupling of aromatic boronic acids with aqueous ammonia and following propargylation by propargyl bromide.A facile, one-pot synthesis of N-aryl propargylamine from aromatic boronic acid, aqueous ammonia, and propargyl bromide has been achieved under microwave-assisted conditions.

•1,2,3-Triazole-directed CH bond mono-acetoxylation.•Cheap acetic acid as the acetoxyl source.•High selectivity and broad substrate scope.A facile and efficient method for the regioselective acetoxylation of 1,4-disubstituted 1,2,3-triazoles via Pd-catalyzed CH bond activation was developed. The cheap acetic acid was applied as the acetoxyl source to convert aromatic sp2 CH bonds into CO bonds in high regioselectivity, employing 1,2,3-triazole as an elegant directing group and K2S2O8 as the oxidant. A range of 1,2,3-triazoles bearing acetoxyl group can be synthesized with the reaction facilely.Download high-res image (58KB)Download full-size image

Pd(OAc)2-catalyzed direct C–H arylation of an arene triazole template has been explored using the triazole ring as a directing group. The N(3)-ortho C–H bond on C(4) aryl of 1,4-disubstituted 1,2,3-triazoles can be selectively arylated, exclusively affording the expected structures. The diarylated products could be selectively formed when the triazole derivative beared a para substituent on C(4) aryl of the heterocycle, while the monoarylated target molecules resulted from substrates with an ortho or meta substituent.