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.