Catalytic Electrophilic Thiocarbocyclization of Allenes

An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence of TMSOTf. Not only electrophilic arylthio reagents but also electrophilic alkylthio reagents worked well under these conditions. Furthermore, the method could be applied to intermolecular azidothiolation of allenes.

Automated summary

An efficient approach for catalytic electrophilic thiocarbocyclization of allenes to synthesize indene-based sulfides with excellent regioselectivities was disclosed. The reactions were conducted at low temperatures using selenide catalysis in the presence of TMSOTf. Both electrophilic arylthio and alkylthio reagents showed good performance under these conditions, and the method was also applicable to intermolecular azidothiolation of allenes.