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A new method for the AgSCF3-mediated radical cascade difunctionalizing trifluoromethythiolation of alkynes with dearomatization is developed. This protocol provides a novel route to SCF3-substituted spirocyclic compounds via the formation of one C-SCF3 bond, one C-C bond, and one C-O double bond in a single step.

A remote OH group-directed metal-free transformation of alkynes to carbonyl compounds has been developed. Using only HOAc and EtOH solvent, this reaction elegantly converts alkynes into valuable ketones by remote hydroxyl group activation. Through comparison and isotope labeling experiments, it was confirmed that the process operates via a hydration reaction involving an acetic acid molecule, instead of a water molecule.

A silver-promoted oxidative cascade cyclization with a phosphorylation/1,5-aryl migration/desulfonylation/dearomatization process is presented here, providing an efficient method to synthesize azaspiro[4.5]decenones with high regioselectivity. The cinnamamidyl radical, which has rarely been reported before, plays a key role in this reaction.

An unprecedented Lewis acid catalyzed [4 + 3] cycloaddition reaction is described that provides a straightforward route to polycyclic products containing an imine-based indole azepine scaffold, starting from readily available internal tertiary alkynols and azides. This cycloaddition protocol provides efficient and atom-economical access to a new class of fascinating imine-containing products in satisfactory yields, which has shown good application in the construction of seven-membered N-heterocycles.

A novel and convenient metal-free nitration and cyclization of 1,6-enynes has been developed. Two C-C bonds and one C-N bond were constructed in one process in this reaction. This transformation is proven to have relatively good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. According to the following experimental facts and related literature reports, a radical pathway was involved in this transformation.

The scalable iron-catalyzed aerobic oxidative reaction is influenced by the steric hindrance of the substrates′ aryl substituents.

The reduction of the pentavalent phosphine in the products to a trivalent one is demonstrated for one product (XII).