Graphitic carbon nitride is a semiconducting material of a graphite-like 2D layered structure. It is well known for its photocatalytic properties, which can be exploited for solar-light-driven water splitting and degradation of organic pollutants. Here, we report its capabilities of catalyzing the reduction of the azo bond by hydrazine to two amines under visible light. This photocatalytic reaction provides a novel, appealing way to reduce azo dye wastes as pollutants other than degradation. With this method, the azo dye wastes can be photochemically converted to amines, which can be used as precursors for new azo dyes.

Glycerophospholipids (GPLs) are structurally diverse and play essential roles in cellular structure, signaling, and metabolism. Electrospray ionization-tandem mass spectrometry (ESI-MS/MS) has been an effective approach for identifying GPLs. How-ever, this approach often fails to differentiate between isomeric lipids. In this work, we have introduced a novel bifunctional tag, nitrophenyl pyrazole, that can react with the double bonds in lipids to simultaneously achieve charge switching and dou-ble bond positional identification. Our results indicate that this approach not only enhances the ionization efficiency of GPLs in the negative mode but also effectively identifies them by providing detailed insights into the fatty acyl chain compositions and position of carbon-carbon bonds in tandem MS. We have applied the method to characterization of polar lipid extracts from complex biological samples without the requirement of authentic lipid reference standards.

Organoboron compounds are indispensable in modern organic synthesis and biomedical research. This study describes the first synthesis of bench-stable boryl dicationic compound via chemical or electrochemical thianthrenation of vinyl MIDA boronate. Notably, the MIDA boryl group plays a crucial role in thianthrenation, suppressing undesired deborylation and promoting exclusive mono-adduct formation via a formal [4+2] cycloaddition pathway. This unique boryl dication enables a transition-metal-free, chemo- and diastereoselective synthesis of aziridinyl boronates, utilizing a broad range of nitrogen nucleophiles. The method demonstrates remarkable generality, practicality, and functional group tolerance, as evidenced by its application to diverse substrates, including the late-stage modification of several drug molecules. The strategic significance of this approach is further highlighted through electrochemical one-pot protocol and multiple downstream transformations of aziridinyl boronates, offering new opportunities for synthetically challenging boron-containing drug-like scaffolds.