Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions
2006 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 14, 4588-4589 p.Article in journal (Refereed) Published
Allyl alcohols were converted to allyl boronic acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron using palladium pincer-complex catalysis. These reactions are regio- and stereoselective proceeding with high isolated yields. Competitive boronation experiments indicate that under the applied reaction conditions the allylic displacement of a hydroxy group is faster than the displacement of an acetate leaving group. It is assumed that the hydroxy group of the allyl alcohol is converted to a diboronic acid ester functionality, which can easily be substituted.
Place, publisher, year, edition, pages
2006. Vol. 128, no 14, 4588-4589 p.
Other Basic Medicine
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-27749DOI: 10.1021/ja060468nOAI: oai:DiVA.org:su-27749DiVA: diva2:217725