Catalytic Halogen Bond Activation in the Benzylic C-H Bond Iodination with Iodohydantoins

Organic Letters
Sascha H CombePeter R Schreiner

Abstract

This letter presents the side-chain iodination of electron-deficient benzylic hydrocarbons at rt using N-hydroxyphthalimide (NHPI) as radical initiator and 1,3-diiodo-5,5-dimethylhydantoin and 3-iodo-1,5,5-trimethylhydantoin (3-ITMH) as iodine source. Addition of a carboxylic acid increased the reactivity due to complex formation with and activation of 3-ITMH by proton transfer and halogen bond formation. No SEAr reactions were observed under the employed reaction conditions. Our method enables convenient product isolation and gives 50-72% yields of isolated products.

References

Aug 31, 2002·Angewandte Chemie·José BarluengaJosé M González
Apr 1, 1965·The Journal of Organic Chemistry·O O ORAZIH E BERTORELLO
Nov 25, 2003·Organic Letters·Raúl Montoro, Thomas Wirth
Dec 2, 2004·Journal of the American Chemical Society·G K Surya PrakashGeorge A Olah
Aug 11, 2005·Angewandte Chemie·José BarluengaJosé M González
Jul 4, 2008·Journal of the American Chemical Society·Boris GalabovWesley D Allen
Aug 13, 2011·Chemistry : a European Journal·Christian LaurenceMohamed J El Ghomari
Jan 27, 2016·Chemical Reviews·Gabriella CavalloGiancarlo Terraneo
Jan 21, 2017·The Journal of Organic Chemistry·Sascha H CombePeter R Schreiner
May 10, 2017·The Journal of Organic Chemistry·Alexander ArtaryanMark Gandelman

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Citations

Jan 18, 2018·Angewandte Chemie·Ronny Tepper, Ulrich S Schubert
Sep 7, 2018·Chemistry : a European Journal·Estefanía Del CastilloKilian Muñiz
Apr 2, 2019·Beilstein Journal of Organic Chemistry·Kelsey B LaMartinaNicholas C Boaz

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