Catalytic Electrophilic Thiocarbocyclization of Allenes

Org Lett. 2021 Nov 19;23(22):8777-8782. doi: 10.1021/acs.orglett.1c03270. Epub 2021 Oct 28.

Abstract

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.