Radical cyclization/bis(pentafluoroethylation) of 1,6-dienes using HCF2CF3-derived CuCF2CF3

We herein describe a domino radical cyclization/bis(pentafluoroethylation) of 1,6-dienes for the synthesis of new classes of pyrrolidine and cyclopentane derivatives containing two C2F5 groups. This reaction is efficient for constructing three carbon-carbon bonds in one step. The reagent [CuCF2CF3] is prepared from inexpensive pentafluoroethane and the reactions conveniently run at room temperature in open air. Moderate to good diastereoselectivies can be obtained favouring the cis products with X-ray structural proof.

Automated summary

We described a novel domino radical cyclization/bis(pentafluoroethylation) of 1,6-dienes for the synthesis of pyrrolidine and cyclopentane derivatives containing two C2F5 groups. This reaction efficiently constructs three carbon-carbon bonds in one step. The reagent [CuCF2CF3] is easily prepared from inexpensive pentafluoroethane and the reaction conveniently runs at room temperature in open air.