Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C–S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Photoinduced organic reactions by pyrene catalysts

Pyrene is one of the most attractive polycyclic aromatic hydrocarbons (PAHs) in photochemistry. Based on their redox properties, pyrenes have potential as photosensitizers. In this review, we aim to summarize recent developments in pyrene-catalyzed photoinduced organic reactions via the process of energy transfer or single electron transfer based on the excited state of pyrenes. 1. Introduction 2. Photolysis involving N–O bond cleavage or decarboxylation 3. (Cyclo)addition reactions with styrenes 4. Transformations via cleavage of C–F, C–I, C–S, and C–N bonds 5. Reactions based on sensitization-initiated electron transfer (SenI-ET) 6. Miscellaneous transformations 7. Conclusion

Electroredox Carbene Organocatalysis with iodine cocatalyst

Oxidative carbene organocatalysis, inspired from Vitamin B1 catalyzed oxidative activation from pyruvate to acetyl coenzyme A, have been developed as a versatile synthetic method. To date, the α-, β-, γ-, δ- and carbonyl carbons of (unsaturated)aldehydes have been successfully activated via oxidative N-heterocyclic carbene (NHC) organocatalysis. In comparison with chemical redox or photoredox methods, electroredox methods, although widely used in mechanistic study, were much less studied in NHC catalyzed organic synthesis. Herein, an electroredox NHC organocatalysis system with iodine cocatalyst was developed. With the help of non-uniform distribution of electrolysis system, NHC and iodine, which was normally not compatible in chemical reaction, cooperated well in the electrochemical system. This cocatalyst system provided general solutions for electrochemical single-electron-transfer (SET) oxidation of Breslow intermediate towards versatile transformations. Radical clock experiment and cyclic voltammetry results suggested an anodic radical coupling pathway.

Earth-Abundant Cobalt based photocatalyst: Visible light induced direct (Het)Arene C-H arylation and CO2 capture

In this work, we have reported a noble metal free heterogeneous photocatalyst to carry out direct (Het)Arene C-H arylation and solvent-free CO2 capture via single-electron transfer processes at room temperature...

Electrochemical C–N bond activation for deaminative reductive coupling of Katritzky salts

Electrosynthesis has received great attention among researchers in both academia and industry as an ideal technique to promote single electron reduction without the use of expensive catalysts. In this work, we report the electrochemical reduction of Katritzky salts to alkyl radicals by sacrificing the easily accessible metal anode. This catalyst and electrolyte free platform has broad applicability to single electron transfer chemistry, including fluoroalkenylation, alkynylation and thiolation. The deaminative functionalization is facilitated by the rapid molecular diffusion across microfluidic channels, demonstrating the practicality that outpaces the conventional electrochemistry setups.