An innovative procedure for the iodoperfluoroalkylation of alkenes/alkynes is described. These reactions, including iodotrifluoromethylations of alkenes, proceed very efficiently under low intensity UVA irradiation in deoxygenated methanol solutions containing catalytic amounts of NaCl or Bu4NCl. Preliminary mechanistic studies indicate that the light-promoted homolytic cleavage of the Rf-I bond that initiates the reaction is facilitated by the halogen bonding interaction between RfI and chloride ions.
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Light-mediated iodoperfluoroalkylation of alkenes/alkynes catalyzed by chloride ions: role of halogen bonding.
Chem Commun (Camb)
July 2018
Institut des Sciences Moléculaires, CNRS UMR 5255, Univ. Bordeaux, 33405 Talence, France.
An innovative procedure for the iodoperfluoroalkylation of alkenes/alkynes is described. These reactions, including iodotrifluoromethylations of alkenes, proceed very efficiently under low intensity UVA irradiation in deoxygenated methanol solutions containing catalytic amounts of NaCl or Bu4NCl. Preliminary mechanistic studies indicate that the light-promoted homolytic cleavage of the Rf-I bond that initiates the reaction is facilitated by the halogen bonding interaction between RfI and chloride ions.
View Article and Find Full Text PDFHalogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions.
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State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China.
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