Journal article

Publication year: 2017

Pages: 6156-6159

Journal: Organic Letters

Volume number: 19

Issue number: 22

DOI Link: https://doi.org/10.1021/acs.orglett.7b03034

Publisher: American Chemical Society

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.

Harvard Citation style: Combe, S., Hosseini, A., Song, L., Hausmann, H. and Schreiner, P. (2017) Catalytic Halogen Bond Activation in the Benzylic C–H Bond Iodination with Iodohydantoins, Organic Letters, 19(22), pp. 6156-6159. https://doi.org/10.1021/acs.orglett.7b03034

APA Citation style: Combe, S., Hosseini, A., Song, L., Hausmann, H., & Schreiner, P. (2017). Catalytic Halogen Bond Activation in the Benzylic C–H Bond Iodination with Iodohydantoins. Organic Letters. 19(22), 6156-6159. https://doi.org/10.1021/acs.orglett.7b03034