7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Abstract

Self-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

Gold-Catalyzed C–O Cross-Coupling Reactions of Aryl Iodides with Silver Carboxylates

“…Significantly, a series of electron-rich para - and meta- substituted aryl iodides reacted well with AgOBz to afford the corresponding aryl esters in excellent yields ( 3c , 3d , 3f , 3h – 3j , 86–90%). On the contrary, the electron-deficient aryl halides were usually preferred in the Ni-catalyzed cross-coupling of carboxylic acid derivatives with aryl halides. ,,,, Moreover, our coupling process showed excellent functional group compatibility toward halides. Fluoride, chloride, and bromide attached to the aromatic ring were unaffected ( 3l – 3q , 70–87%).…”

Visible-Light-Driven α-Substituted Amines Enabled by In Situ Formation of Amine Substrate Aggregates

“…In 2021, our group reported 2,3-dicyanopyrazino phenanthrene (DCPP) aggregates that were formed in situ by controlling the concentration of DCPP monomers in organic solvents . After DCPP aggregates were formed, they exhibited different photo- and electrochemical properties from their single molecules because their energy levels (e.g., the highest occupied molecular orbital [HOMO] and lowest unoccupied molecular orbital [LUMO]) can be changed by the π–π stacking effect .…”