1025027-36-4Relevant articles and documents
Aqueous-Medium Carbon-Carbon Bond-Forming Radical Reactions Catalyzed by Excited Rhodamine B as a Metal-Free Organic Dye under Visible Light Irradiation
Yoshioka, Eito,Kohtani, Shigeru,Jichu, Takahisa,Fukazawa, Takuya,Nagai, Toyokazu,Kawashima, Akira,Takemoto, Yoshiji,Miyabe, Hideto
, p. 7217 - 7229 (2016)
The utility of rhodamine B as a water-soluble organic photocatalyst was studied in the cascade radical addition-cyclization-trapping reactions under visible light irradiation. In the presence of (i-Pr)2NEt, the electron transfer from the excited rhodamine B to perfluoroalkyl iodides proceeded smoothly to promote the carbon-carbon bond-forming radical reactions in aqueous media. When i-C3F7I was employed as a radical precursor, the aqueous-medium radical reactions proceeded even in the absence of (i-Pr)2NEt. In these reactions, the direct electron transfer from the excited singlet state of rhodamine B would take place. Furthermore, the cleavage of the C-I bond in less reactive i-PrI could be achieved by the reductive electron transfer from the excited rhodamine B, which was confirmed by the fluorescence quenching of rhodamine B with the addition of i-PrI.
Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate
Rosso, Cristian,Williams, Jason D.,Filippini, Giacomo,Prato, Maurizio,Kappe, C. Oliver
supporting information, p. 5341 - 5345 (2019/07/03)
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.
Sodium dithionite initiated addition of CF2Br2, CF3I and (CF3)2CFI to allylaromatics. Synthesis and the reactivity of 4-aryl-1,1-difluorodienes and 4-aryl-1,1-bis(trifluoromethyl)dienes
Ignatowska, Jolanta,Dmowski, Wojciech
, p. 997 - 1006 (2008/02/10)
Sodium dithionite initiated addition of CF2Br2, CF3I and (CF3)2CFI to the terminal double bond of allylbenzenes and of (CF3)2CFI to allylpyridines in a MeCN/H2O system