A novel copper-catalyzed cycloaddition of diaryl disulfides to heterobicyclic alkenes has been developed. The CS and CC bonds can be formed simultaneously on the CC bond of the olefins via a single-step cycloaddition to afford a series of 2,3-dihydrobenzo­[b]­thiophene derivatives. This reaction exhibits excellent diastereoselectivity and relatively broad substrate scope. Various functional groups attached to the substrates are tolerated in this protocol to give the corresponding exo adducts in moderate yields.

A novel ICl/AgNO3 co-catalyzed radical oxidation of diaryl- and alkylarylalkynes into 1,2-diketones is reported. The reaction proceeded smoothly under mild conditions and generated 1,2-diketones in moderate to good yields with a good tolerance of functional groups. Furthermore, the obtained C4-(1,2-diketoaryl)­isoxazoles could react smoothly with 1,2-diaminobenzene to form C4-(3-arylquinoxalin-2-yl)­isoxazoles. At last, a new one-pot strategy for the synthesis of quinoxalines from 1,2-diphenylethynes and 1,2-diaminobenzene is also reported.

A sulfa-Michael/aldol/lactonization cascade reaction has been established to construct isotetronic acid-fused thiochromanes in a highly stereoselective fashion (≥11:1 dr, 35–98% ee). The tricyclic products were obtained in 35–99% isolated yields in the presence of a bifunctional squaramide. Three reactive sites of β,γ-unsaturated α-ketoester, including the less-explored ester carbonyl group, were sequentially utilized to construct two fused heterocycles in a one-pot operation.

A new 1,3-dipolar cycloaddition of oxa(aza)bicyclic alkenes with nitrones has been developed without any catalyst and additive under mild conditions. The proposed concerted mechanism is investigated by DFT calculations of the reaction pathways.

A novel copper-catalyzed complete diastereoselective 1,2-difunctionalization of oxabicyclic alkenes has been developed. Two C−S bonds were constructed simultaneously on the oxabenzonorbornadienes leading to βthiocyanato thioethers through the three-component (oxabicyclic alkenes, aryl iodides, and potassium thiocyanate), onepot reaction. Various functional groups attached to the substrates were tolerated in this protocol to afford the corresponding β-thiocyanato thioether products in moderate yields.