Two Cascade Processes Initiated by the Insertion of Benzyne into the Se═O Bond.

Two sets of cascade processes have been realized, both of which were initiated with a benzyne insertion into the Se═O bond. The key factors to differentiate these processes are based on the structures of diaryl selenium oxides and reaction conditions. When diaryl selenium oxides containing an ortho weak σ-electron-withdrawing group were used, triarylselenonium salts were obtained at room temperature, while ortho-(aryloxy)phenyl phenyl selanes could be produced from diaryl selenium oxides at 100 °C.

Diverse Synthesis of Triarylselenonium Salts and o-(Alkoxy)aryl Aryl Selanes via Insertion of Benzyne into the Se═O Bond.

An insertion of benzyne into the Se═O bond has been realized. In this reaction, two types of compounds containing selenium could be synthesized from different substrates. When diaryl selenium oxides were used, triarylselenonium salts were furnished, while o-(alkoxy)phenyl phenyl selanes could be produced from aryl alkyl selenium oxides.