Direct Organocatalytic Oxo-Metathesis, a trans-Selective Carbocation-Catalyzed Olefination of Aldehydes
2015 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 8, 1834-1839 p.Article in journal (Refereed) Published
A direct organocatalytic carbonyl/olefin oxo-metathesis has been developed. The reaction is catalyzed by trityl tetrafluoroborate (TrBF4) and utilizes unactivated alkenes for the olefination of aromatic aldehydes to give trans -alkylstyrenes in yields of 44-85% with only acetone as the byproduct. The pronounced Lewis acidity of the carbocation results in unusual reactivity that is proposed to catalyze a stepwise [2+2] cycloaddition to give an oxetane intermediate. Fragmentation of the latter in a formal retro [2+2] reaction gives the oxo-metathesis product.
Place, publisher, year, edition, pages
2015. no 8, 1834-1839 p.
IdentifiersURN: urn:nbn:se:kth:diva-164466DOI: 10.1002/ejoc.201403651ISI: 000351054500025OAI: oai:DiVA.org:kth-164466DiVA: diva2:806882
FunderSwedish Research Council
QC 201504222015-04-222015-04-172015-04-22Bibliographically approved