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Published June 11, 2024 | Version v1
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Photoenzymatic asymmetric incorporation of fluorinated motifs into olefins

  • 1. University of Illinois Urbana-Champaign

Description

Enzymes capable of assimilating fluorinated feedstocks are scarce, which poses a challenge for the biosynthesis of fluorinated compounds used in pharmaceuticals, agrochemicals, and materials. We develop a photoenzymatic hydrofluoroalkylation that adeptly integrates fluorinated motifs into olefins. The photoinduced promiscuity of flavin-dependent ene-reductases enables generation of carbon-centered radicals from iodinated fluoroalkanes, which are directed by the photoenzyme to engage enantioselectively with olefins. This approach facilitates stereocontrol through interaction between a singular fluorinated unit and the enzyme, securing high enantioselectivity at β-, γ-, or δ-positions of fluorinated groups via enzymatic hydrogen atom transfer, a process notably challenging with conventional chemocatalysis. This work advances enzymatic strategies for integrating fluorinated chemical feedstocks and opens new avenues for asymmetric synthesis of fluorinated compounds.

Notes

Funding provided by: United States Department of Energy
Crossref Funder Registry ID: https://ror.org/01bj3aw27
Award Number: DE-SC0018420

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