Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate
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.
Rosso, Cristian,Williams, Jason D.,Filippini, Giacomo,Prato, Maurizio,Kappe, C. Oliver
supporting information
p. 5341 - 5345
(2019/07/03)
Iron-Catalyzed Carboiodination of Alkynes
An iron-catalyzed carboiodination of alkynes with alkyl iodides at room temperature was developed. This method could provide synthetically useful vinyl iodides with general alkyl chains, fluoroalkyl group, ester, and cyano group. Conjugated alkynes or unconjugated alkynes were both suitable for this transformation. A radical pathway was proposed for the mechanism and acetyl tert -butyl peroxide was selected as the radical initiator. Alkenes could also be applied to this chemistry and produce more complex alkyl iodides.
Deng, Weili,Li, Yajun,Li, You-Gui,Bao, Hongli
p. 2974 - 2980
(2018/04/24)
A NEW TIN(II) CHLORIDE-SILVER(I) ACETATE OR -LEAD(II) BROMIDE REAGENT FOR THE ADDITION OF F-ALKYL IODIDES TO ALKENES
A tin(II) chloride-silver(I) acetate or tin(II) chloride-lead(II) bromide reagent can efficiently promote the addition of F-alkyl iodides to various alkenes in anhydrous methanol at room temperature to afford the corresponding F-alkylated iodides in fairl
Ishihara, Takashi,Kuroboshi, Manabu
p. 1611 - 1618
(2007/10/02)
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