Radical-Mediated Hydroperfluoroalkylation of Unactivated Alkenes

The direct hydroperfluoroalkylation of a wide range of unactivated alkenes has been achieved at room temperature with readily available iodoperfluoroalkanes using 4-tert-butylcatechol as a source of hydrogen atom and triethylborane. The hydrotrifluoromethylation could also be achieved under these conditions using gaseous trifluoromethyl iodide. An experimentally simple two-step, one-pot hydrotrifluoromethylation process using the easy-to-use trifluoromethanesulfonyl chloride as the source of trifluoromethyl radicals has also been developed. Using these two approaches, a broad range of substrates, including isoprenoid natural products, were efficiently derivatized.

Automated summary

The direct hydroperfluoroalkylation of unactivated alkenes using iodoperfluoroalkanes and 4-tert-butylcatechol as a hydrogen source has been achieved at room temperature. Hydrotrifluoromethylation can also be achieved using gaseous trifluoromethyl iodide. Additionally, a simple two-step, one-pot hydrotrifluoromethylation process using trifluoromethanesulfonyl chloride as a trifluoromethyl radical source has been developed.