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Comprehensive Summary: A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H2 evolution has been developed. The photoelectrochemical C—H silylation depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated through the light‐induced homolytic cleavage of Cl2, in which Cl2 was produced by electrochemical oxidation of chloride. A large number of silylated heterocyclic molecules are rapidly constructed in satisfactory yields without relying on oxidants and metal reagents. [ABSTRACT FROM AUTHOR]

Comprehensive Summary: A photoelectrochemical approach for the C—H silylation of heteroarenes through dehydrogenation cross‐coupling with H2 evolution has been developed. The photoelectrochemical C—H silylation depends on hydrogen atom transfer (HAT) from silanes to Cl‐radical generated through the light‐induced homolytic cleavage of Cl2, in which Cl2 was produced by electrochemical oxidation of chloride. A large number of silylated heterocyclic molecules are rapidly constructed in satisfactory yields without relying on oxidants and metal reagents. [ABSTRACT FROM AUTHOR]

Abstract: An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter‐ and intramolecular annulation reactions required noble‐metal catalysts and are mostly limited to terminal alkenes or 1,3‐dienes. The electrosynthesis employs the easily available and inexpensive ferrocene as the molecular catalyst and is compatible with di‐, tri‐ and even tetrasubstituted alkenes to construct indolines as well as the more challenging azaindolines. Employing the newly developed electrosynthesis as a key step, the total synthesis of marine alkaloid (±)‐hinckdentine A has been achieved in 12 steps (longest linear sequence) from commercially available materials. [ABSTRACT FROM AUTHOR]