Photoinduced Copper-Catalyzed 1,2-Difunctionalization of 1,3-Dienes with Aryl Diselenides.

Described herein is a photoinduced copper-catalyzed 1,2-difunctionalization of 1,3-dienes. The selenium atom radical was generated by the visible light irradiation of diselenides, triggering radical addition with 1,3-dienes to form allyl radical intermediate. Subsequent rapid Z/E isomerization allowed for thermodynamically favorable intermediate formation and enabled copper catalyzed stereoselective functionalization with various nucleophiles.

Copper-Catalyzed Oxidative Dearomatized Oxyalkylation of Indoles with Alcohols: Synthesis of 3-Alkoxy-2-Oxindoles.

Described herein is a copper-catalyzed efficient oxidative dearomatized functionalization of indoles by using alcohols as the nucleophiles. Various 3-alkoxy-2-oxindoles were accessible with good isolated yields. The synthetic potential applications are demonstrated by the large-scale reaction, as well as the derivatization of the desired 3-alkoxy substituted-2-oxindole products.

Site-Specific Radical Alkylation of Aryl Cyanide: Visible-Light, Photoredox-Catalyzed, Three-Component Arylalkylation of [1.1.1]Propellane.

We report herein a three-component radical arylalkylation of [1.1.1]propellane toward the synthesis of aryl-substituted bicyclo[1.1.1]pentane derivatives. The use of electron-deficient aryl cyanide as an aryl group source not only reduces the energy barrier of the arylation of the nucleophilic alkyl radical species, but also suppresses the electrophilic Friedel-Crafts alkylation process, enabling the present site-selective arylalkylation.