Photoinduced Decarboxylative Phosphorothiolation of N-Hydroxyphthalimide Esters.

A visible-light-induced protocol for the synthesis of phosphorothioates is developed by employing the Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. This novel synthesis method utilizes carboxylic acids as raw material, which is stable, cheap, and commercially available. Scope studies show that this reaction has good compatibility of functional groups. Notably, both the synthesis of steric hindrance phosphorothioates and the later modification of some bioactive compounds are successfully achieved.

C-H Imidation and Dual C-H Bond Aminobromination of Five-Membered Heterocycles.

Here, we report a practical C-H imidation of five-membered heterocycles under metal-free conditions. We also report the first dual C-H bond aminobromination of thiophenes, with benzotriazole, saccharin, 1,2,4-triazole, benzimidazole, pyrazole, 4-bromopyrazole, 5-methyltetrazole, and dibenzenesulfonimides as effective amine sources. Mechanistic studies support the radical pathway of the imidation and aminobromination reactions.

Copper-catalyzed C-N bond formation with imidazo[1,2-a]pyridines.

An efficient Cu-catalyzed method for direct C-N bond formation on the C-3 position of imidazo[1,2-a]pyridines is reported. The robust copper catalyst tolerated a wide range of functional groups and set the stage for the synthesis of diversely decorated imidazo[1,2-a]pyridines. Preliminary experimental results show that the reaction mechanism is consistent with C-3 radical functionalization.

A novel metal-free amidosulfenylation of alkenes leading to ß-azolyl sulfides.

A novel and environmentally benign method for C-S and C-N bond formation by the direct amidosulfenylation of alkenes has been developed under metal-free conditions. Various alkenes and azoles were transformed into the corresponding ß-azolyl sulfides in ionic liquids. The wide substrate scope, good functional group tolerance, and ease of operation make this reaction attractive for the synthesis of nitrogen- and sulfur-containing molecules.