Issue 54, 2018

Light-mediated iodoperfluoroalkylation of alkenes/alkynes catalyzed by chloride ions: role of halogen bonding

Abstract

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.

Graphical abstract: Light-mediated iodoperfluoroalkylation of alkenes/alkynes catalyzed by chloride ions: role of halogen bonding

Supplementary files

Article information

Article type
Communication
Submitted
06 Apr 2018
Accepted
07 Jun 2018
First published
08 Jun 2018

Chem. Commun., 2018,54, 7451-7454

Light-mediated iodoperfluoroalkylation of alkenes/alkynes catalyzed by chloride ions: role of halogen bonding

R. Beniazza, L. Remisse, D. Jardel, D. Lastécouères and J. Vincent, Chem. Commun., 2018, 54, 7451 DOI: 10.1039/C8CC02765J

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