Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Visible-light-driven multicomponent reactions to access <i>S</i>-alkyl phosphorothioates using elemental sulfur as the sulfur source

Photoinduced Decarboxylative Phosphorothiolation of N-Hydroxyphthalimide Esters.

Heteroatom-heteroatom linkage, with S-S bond as a presentative motif, served a crucial role in biochemicals, pharmaceuticals, pesticides, and material sciences. Thus, preparation of the privileged scaffold has always been attracting tremendous attention from the synthetic community. However, classic protocols suffered from several drawbacks, such as toxic and unstable agents, poor functional group tolerance, multiple steps, and explosive oxidizing regents as well as the transitional metal catalysts. Electrochemical organic synthesis exhibited a promising alternative to the traditional chemical reaction due to the sustainable electricity can be employed as the traceless redox agents. Hence, toxic and explosive oxidants and/or transitional metals could be discarded under mild reaction with high efficiency. In this context, a series of electrochemical approaches for the construction of heteroatom-heteroatom bond were reviewed. Notably, most of the cases illustrated the dehydrogenative feature with the clean energy molecules hydrogen as the sole by-product.

Electrochemical Heteroatom-Heteroatom Bond Construction

Copper-Catalyzed Multicomponent Trifluoromethylphosphorothiolation of Alkenes: Access to CF3-Containing Alkyl Phosphorothioates.

Regioselective C-H Phosphorothiolation of (Hetero)arenes Enabled by the Synergy of Electrooxidation and Ultrasonic Irradiation.

An I2O5 promoted tandem Strecker/C(sp3)–H amination reaction of pyridine-2-carboxaldehydes, benzylamines and NH4SCN has been reported. This multicomponent reaction that allows the single-step construction of biologically important cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity was realized for the first time. Moreover, the use of safe and easy-to-handle NH4SCN as a surrogate cyanating agent makes this protocol appealing for potential applications.

Qing Yang

Papers

Regioselective C-H Phosphorothiolation of (Hetero)arenes Enabled by the Synergy of Electrooxidation and Ultrasonic Irradiation.

Tandem Strecker/C(sp3)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH4SCN as a cyanating agent