Regioselective Dye-Induced Photocleavage of Epoxides as an Alternative Mild Synthetic Route to a Targeted Alcohol Functionality
Anthony A. Provatas A B , Gary A. Epling , James D. Stuart A and Aliaksandr Yeudakimau A
+ Author Affiliations
- Author Affiliations
A University of Connecticut, Center for Environmental Sciences and Engineering, 3107 Horsebarn Hill Road Unit 4210, Storrs, Connecticut 06269-4210, USA.
B Corresponding author. Email: anthony.provatas@uconn.edu
Australian Journal of Chemistry 68(3) 500-504 https://doi.org/10.1071/CH14327
Submitted: 23 May 2014 Accepted: 3 July 2014 Published: 22 September 2014
Abstract
The regioselective cleavage of epoxides using visible light and a catalytic dye is reported in this study as an alternative mild synthetic approach. The epoxide radical anion is generated via visible light in an electron transfer reaction, induced by non-toxic dyes, leading to ring opening and formation of the corresponding alcohol with the hydroxyl group on the less substituted carbon in excellent yields.
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