Zu-Yu Mo

We have developed an electrochemical iodine-mediated electrophilic spirocyclization/nucleophilic substitution cascade strategy for the spirocyclization of 3-(2-isocyanoethyl)indole with cysteine-containing peptides and organochalcogen compounds.

Benzotriazoles and benzenesulfonamides arewidely present in various bioactive molecules, so the development of mild and convenientsynthetic strategies to synthesize compounds containing these functional groups is crucial for discovering candidate therapeutic drugs with higher efficacy and fewer side effects. Herein, we report an imidoyl radical‐involved electrochemical method for the difunctionalization of isocyanides with benzotriazoles and benzenesulfonamides, and also realize the electrochemical reaction of isocyanides with benzotriazoles to construct guanidine derivatives. This strategy achieves the difunctionalization of isocyanide under the action of a base, with benzotriazole as the radical precursor and sulfonamide as the nucleophile. Either does not require a chemical oxidant and can be carried out at room temperature.

We have developed a mild and effective electrocatalytic three-component cyclization reaction of terminal alkynes, allyl dimethyl esters, and diselenides to synthesize valuable selenium-containing cyclopentene derivatives.

An electrochemically promoted protocol for the synthesis of (4-trifluoromethyl)isoxazoles has been successfully developed through the oxidative cyclization reaction of 2-alkyn-1-one O-methyloximes with CF₃SO₂Na. This newly developed protocol exhibits higher step economy and higher atom economy compared to existing methods. Additionally, the electrochemical cyclization reaction of N-(diphenylphosphoryl)acrylamides with CF₃SO₂Na has also been achieved, yielding a series of unexplored trifluoromethyl phosphoramide compounds without the need for additional catalysts or external oxidants. This method provides an efficient and sustainable approach to obtain various isoxazoles and nitrogen-phosphorus heterocycles bearing a CF₃ moiety.

An electrochemical cyclization/spirocyclization hydroarylation via reductive dearomatization of a series of nonactivated arenes including N-substituted indoles, indole-3-carboxamide derivatives, and iodo-substituted benzamides is described. This protocol boasts high atom efficiency, broad substrate applicability, and excellent selectivity. Utilizing a simple undivided cell, various nonactivated arenes undergo cyclization/spirocyclization through the intramolecular addition of aryl radicals to an aromatic ring, yielding 50 indolines, spirocyclizative hydroarylation products, and phenanthridinones.

2‐(chalcogen)benzothiazoles are frequently used as core structures for the development of pharmaceutical agents. A strategy for the synthesis of 2‐(chalcogen)benzothiazoles under electrooxidative conditions using isocyanides, thiols or diselenides as substrates was developed. This protocol allows access to structurally diverse 2‐(chalcogen)benzothiazoles in good yields and with good functional group tolerance, which does not require heavy metal catalysts and exogenous oxidants. Furthermore, gram‐scale synthesis was performed to demonstrate the scale‐up applicability of this reaction.

An electrochemical oxidative difunctionalization of diazo compounds with diselenides and nucleophiles has been developed. This innovative approach yields a diverse array of selenium-containing pyrazole esters and alkoxy esters, overcoming the limitations of traditional synthesis methods. Remarkably, various nucleophiles, including acids, alcohols, and pyrazoles, can be seamlessly incorporated. Notably, this protocol boasts high atom efficiency, excellent functional group tolerance, and good efficiency and operates under transition metal- and oxidant-free conditions, distinguishing it in the field.

We have developed a mild method for selenium catalyzed intramolecular rearrangement of N -aryloxyamides to produce para amination products under electrochemical conditions. The method has the advantages of high efficiency, high atom utilization and environmental friendliness.

Organoselenium compounds are crucial molecules that are utilized extensively in diverse fields such as medicine, agriculture, catalysis, and organic materials. The incorporation of selenium atoms into organic molecules holds significant importance in synthetic chemistry. Organic electrochemical synthesis, a green, mild, and efficient strategy, has displayed remarkable potential for organoselenium chemistry synthesis. Consequently, there has been substantial interest in recent years in researching electrochemically mediated synthesis of organoselenium compounds. This review provides an overview of the progress made in electrochemically mediated organic selenium reactions over the last decade, including electrochemical mediated selenium catalysis, electrochemical oxidation of diselenide coupling, and electrochemical oxidation tandem selenocyclization. The scope, limitations, and mechanisms of those reactions are emphasized.1 Introduction2 Electrochemical Selenium-Catalyzed Reactions3 Electrochemically Mediated Coupling of Aromatic/Heterocyclic Rings with Diselenides4 Electrochemically Mediated Tandem Selenocyclization5 Conclusion

This study presents an approach for the electrochemical oxidation ring‐opening/cyclization reaction of methylcyclopropane with diselenides/ditellurides, leading to the synthesis of diverse 2‐substituted‐3,4‐dihydronaphthalene derivatives with exceptional selectivity and efficiency. This methodology involves C(sp³)−H functionalization, ring opening and cyclization processes. One characteristic of this method is its ability to accommodate a wide range of substrates with various functional groups.