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- Title
Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.
- Authors
Fumagalli, Gabriele; Rabet, Pauline T. G.; Boyd, Scott; Greaney, Michael F.
- Abstract
[Cu(dap)2]Cl effectively catalyzes azide addition from the Zhdankin reagent to styrene-type double bonds, and subsequent addition of a third component to the benzylic position. In the presence of light, a photoredox cycle is implicated with polar components such as methanol or bromide adding to a benzylic cation. In the absence of light, by contrast, double azidation takes place to give diazides. Therefore, regioselective double functionalization can be achieved in good to excellent yields, with a switch between light and dark controlling the degree of azidation.
- Subjects
AZIDATION; STYRENE; CHEMICAL bonds; COPPER catalysts; CATIONS
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 39, p11481
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201502980