α-Arylation by Rearrangement: On the Reaction of Enolates with Diaryliodonium Salts
2010 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 28, 8251-8254 p.Article in journal (Refereed) Published
Surprising equilibration: A new mechanism for the title reaction is supported by DFT calculations and experimental observations. The CI and OI intermediates are isoenergetic and equilibrate quickly. Thus, any chiral information induced in the initial complex will be destroyed. In the final CC bond-forming step, a [2,3]-rearrangement from the OI bonded intermediate is slightly preferred over the [1,2]-elimination from the CI bonded isomer (see scheme).
Place, publisher, year, edition, pages
2010. Vol. 16, no 28, 8251-8254 p.
arylation, density functional calculations, hypervalent compounds, iodanes, reaction mechanisms
Chemical Sciences Organic Chemistry
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-50196DOI: 10.1002/chem.201001110ISI: 000280819100003OAI: oai:DiVA.org:su-50196DiVA: diva2:380656
FunderSwedish Research Council, 621-2008-3709Carl Tryggers foundation , 08:288Carl Tryggers foundation , 09:281Knut and Alice Wallenberg Foundation
authorCount :42010-12-212010-12-212015-09-22Bibliographically approved