Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 39, Pages 11481-11484Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502980
Keywords
azides; copper; heterocycles; photochemistry; radicals
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Funding
- EPSRC
- University of Manchester
- AstraZeneca
- Engineering and Physical Sciences Research Council [1468092] Funding Source: researchfish
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[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.
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