Arylation with Unsymmetrical Diaryliodonium Salts: A Chemoselectivity Study
2013 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 31, 10334-10342 p.Article in journal (Refereed) Published
Phenols, anilines, and malonates have been arylated under metal-free conditions with twelve aryl(phenyl)iodonium salts in a systematic chemoselectivity study. A new “anti-ortho effect” has been identified in the arylation of malonates. Several “dummy groups” have been found that give complete chemoselectivity in the transfer of the phenyl moiety, irrespective of the nucleophile. An aryl exchange in the diaryliodonium salts has been observed under certain arylation conditions. DFT calculations have been performed to investigate the reaction mechanism and to elucidate the origins of the observed selectivities. These results are expected to facilitate the design of chiral diaryliodonium salts and the development of catalytic arylation reactions that are based on these sustainable and metal-free reagents.
Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2013. Vol. 19, no 31, 10334-10342 p.
arylation, chemoselectivity, DFT calculations, hypervalent compounds, ligand exchange
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-75778DOI: 10.1002/chem.201300860ISI: 000321983700034OAI: oai:DiVA.org:su-75778DiVA: diva2:523890
FunderSwedish Research Council, 621-2011-3608