Trifluoromethylation of alkenes by visible light photoredox catalysis

Naeem Iqbal; Sungkyu Choi; Eunjin Kim; Eun Jin Cho

doi:10.1021/jo3022346

Trifluoromethylation of alkenes by visible light photoredox catalysis

J Org Chem. 2012 Dec 21;77(24):11383-7. doi: 10.1021/jo3022346. Epub 2012 Nov 30.

Authors

Naeem Iqbal¹, Sungkyu Choi, Eunjin Kim, Eun Jin Cho

Affiliation

¹ Department of Chemistry and Applied Chemistry, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, ansan, Kyeonggi-do 426-791, Republic of Korea.

PMID: 23167602
DOI: 10.1021/jo3022346

Abstract

A method for trifluoromethylation of alkenes has been developed employing visible light photoredox catalysis with CF(3)I, Ru(Phen)(3)Cl(2), and DBU. This process works especially well for terminal alkenes to give alkenyl-CF(3) products with only E-stereochemistry. The mild reaction conditions enable the trifluoromethylation of a range of alkenes that bear various functional groups.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Catalysis
Chlorofluorocarbons, Methane / chemistry*
Light*
Oxidation-Reduction
Photochemical Processes*

Substances

Alkenes
Chlorofluorocarbons, Methane
fluoroform