Issue 18, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jun 2022
Accepted
02 Aug 2022
First published
03 Aug 2022

Org. Chem. Front., 2022,9, 4969-4974

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

Z. Luo and G. C. Tsui, Org. Chem. Front., 2022, 9, 4969 DOI: 10.1039/D2QO00919F

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