Synthesis of 3‑Cyanoindole Derivatives Mediated by Copper(I) Iodide Using Benzyl Cyanide

Copper-mediated direct and regioselective C3-cyanation of indoles using benzyl cyanide as the cyanide anion source is presented. A wide range of indoles undergo cyanation smoothly by employing a reaction system of copper­(I) iodide under open-to-air vessels

Carbon–Boron Bond Cross-Coupling Reaction Catalyzed by −PPh₂ Containing Palladium–Indolylphosphine Complexes

This study describes the application of indolylphosphine ligands with a diphenylphosphino moiety to the palladium-catalyzed borylation of aryl chlorides. The combination of palladium metal precursor with PPh₂-Andole-phos, which comprises an inexpensive −PPh₂ group, provides highly effective catalysts for the borylation of aryl chlorides. A range of functional groups such as −CN, −NO₂, −CHO, −COMe, −COOMe, and −CF₃ was compatible, and the catalyst loading down to 0.025 mol % of Pd can be achieved. The Pd/PPh₂-Andole-phos system is able to catalyze both borylation reaction and Suzuki–Miyaura coupling reaction in a one-pot sequential manner for the direct synthesis of biaryl compounds in excellent yields

Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides