Construction Of Fused Multifunctionalized Dibenzoselenophene Derivatives From Tetraynes

Cycloaddition reaction to construct new carbon-carbon bond has become one of the important methods in modern synthetic chemistry.Benzynes are important intermediates and have unique advantages in building complex polycyclic compounds and natural products,gradually become the active fields in organic synthesis.Here,we report the reaction of tetraynes with diphenyl diselenide(PhSeSePh)to produce various multi-functionalized dibenzoselenophenes in good to excellent yields in the absence of metals,catalysts,bases,or oxidants.The reactions are green because they avoiding the waste of resources caused by the intermediate separation process.This approach requires no directing groups but exhibits excellent regioselectivity.Therefore,polysubstituted benzoselenophenes in good to excellent yields can be produced via the HDDA reaction,free radical reaction and C–H activation.This method provides a direct,efficient and economical way for constructing fused dibenzoselenophene compounds.Under the temperature of 90? we have generated 29 polycyclic compounds with dibenzoselenophene skeleton structure.All products were characterized by IR?NMR and HRMS.Five of the products were confirmed by X-ray single crystal structure analysis.