Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 10, Pages 3485-3490Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504852
Keywords
density functional calculations; hypervalent compounds; radical reactions; radicals; synthetic methods
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Funding
- Westfalische Wilhelms-University Munster
- Deutsche Forschungsgemeinschaft (DFG)
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A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.
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