A difunctionalization-type perfluoroalkylation reaction for styrenes

August 8, 2018

Contributing to the supply of high value–added compounds conveniently at low cost

RIKEN’s Synthetic Organic Chemistry Laboratory and RIKEN CSRS have succeeded in developing difunctionalization-type perfluoroalkylation reactions under metal-free conditions based on the unique reactivity between styrenes and diacyl peroxides.

Perfluoroalkyl groups can improve lipophobicity and metabolic stability when introduced into organic compounds. Since this property offers a powerful means for improving pharmacokinetics in the development of pharmaceuticals and agricultural chemicals, practical and efficient synthesis methods for perfluoroalkyl compounds are needed.

The joint research team succeeded in developing difunctionalizaion-type trifluoromethylations, oxy- and amino-perfluoroalkylations, of styrenes with perfluorodiacyl peroxide generated in-situ from perfluoro acid anhydrides as inexpensive and easily obtainable perfluoro sources.

Normally, similar reactions required controlling reactivity and selectivity with transition metal catalysts. This research demonstrated that it is possible to efficiently obtain the desired products under metal free conditions by making use of the strong oxidizing power of perfluorodiacyl peroxide. Additionally, the compounds obtained are easy to derive and useful for synthesizing organic molecules with various skeletons.

 

Original article
Chemical Science doi:10.1039/c8sc02547a
E. Valverde, S. Kawamura, D. Sekine, M. Sodeoka,
"Metal-free alkene oxy- and amino-perfluoroalkylation via carbocation formation by using perfluoro acid anhydrides: unique reactivity between styrenes and perfluoro diacyl peroxides".

Contact
Shintaro Kawamura; Research Scientist
Mikiko Sodeoka; Group Director
Catalysis and Integrated Research Group