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Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate

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journal contribution
posted on 21.06.2019, 18:06 by Cristian Rosso, Jason D. Williams, Giacomo Filippini, Maurizio Prato, C. Oliver Kappe
Two efficient continuous flow iodo­perfluoro­alkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.