Iodopentafluorosulfanylation of [1.1.1]propellane and further functionalizations

Pentafluorosulfanylated (SF 5 -) aromatics have shown great potential in drugs, and the bioisosteric replacement of aromatic ring with bicyclo[1.1.1]pentane (BCP) unit has attracted considerable attention recently. Consequently, pentafluorosulfanylated bicyclo[1.1.1]pentanes (SF 5 -BCPs) should have application in the realm of drug discovery. In this study, a one-pot iodopentafluorosulfanylation of [1.1.1]propellane with SF 5 Cl and CH 2 I 2 for the practical synthesis of iodopentafluorosulfanylated bicyclo[1.1.1]pentane (SF 5 -BCP-I) was developed. SF 5 -BCP-I was the first example of SF 5 -BCPs that could be transformed. The first general method to access SF 5 -substituted bicyclo[1.1.1]pentane derivatives was demonstrated through photoredox-catalyzed radical addition of SF 5 -BCP-I to alkenes and alkynes.