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Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation
Author(s) -
Hartmann Marcel,
Li Yi,
MückLichtenfeld Christian,
Studer Armido
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504852
Subject(s) - hypervalent molecule , radical , chemistry , aryl , alkene , reagent , aryl radical , malonate , photochemistry , iodine , adduct , medicinal chemistry , organic chemistry , alkyl , catalysis
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.