Synthesis of Seleno Oxindoles via Iodine-induced Radical Cyclization of N-arylacrylamides with Diorganyl Diselenides

A mild radical cascade cyclization of N-arylacrylamides with diselenides for the preparation of oxindoles via iodine oxidation is disclosed, which provide an eco-friendly process for the construction of C–Se bond. 25 Examples of N-arylacrylamide substrates were investigated with excellent yields. Besides, the tandem cyclization of acrylamide with diphenyl disulfide was also applicable under the same condition.

Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations would indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex...

Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles

An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.

Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

A photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.