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Organoselenium catalysis has attracted increasing interest in recent years. This Cluster highlights recent key advances in this area regarding the functionalization of alkenes, alkynes, and arenes by electrophilic selenium catalysis, selenonium salt catalysis, selenium-based chalcogen-bonding catalysis, and Lewis basic selenium catalysis. These achievements might inspire and help future research.1 Introduction2 Electrophilic Selenium Catalysis3 Selenonium Salt Catalysis4 Selenium-Based Chalcogen-Bond Catalysis5 Lewis Basic Selenide Catalysis6 Conclusion

An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.

Efficient synthesis of trifluoromethylthiolated molecules, especially for chiral ones, is in great demand for the development of drugs. Developing new catalysis mode and new catalysts is the key to quickly expand this area. Our group discovered that Lewis basic chalcogenide catalysts could activate the N–SCF3 bond, which provided a new way for non- and asymmetric trifluoromethylthiolation. This Synpacts article highlights the recent advances we have achieved. 1 Introduction 2 Selenide-Catalyzed Nonasymmetric Trifluoromethylthiolation 3 Chiral Sulfide-Catalyzed Enantioselective Trifluoromethylthiolation 4 Conclusion

Pentafluorophenyl triazolium carbenes, widely used in NHC catalysis, can decompose by several mechanisms. Under high concentration conditions, the azolium may undergo a pentafluorophenyl exchange by a proposed SNAr mechanism to give an inactive salt. In the presence of appropriate substrates, cyclization on the ­ortho-position of the arene can occur, also by SNAr. These adducts provide a potential pathway for catalyst decomposition and serve as a caveat to the development of new reactions and catalysts.