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Direct Organocatalytic Oxo-Metathesis, a trans-Selective Carbocation-Catalyzed Olefination of Aldehydes
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0003-1933-4193
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
Abstract [en]

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.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-164466DOI: 10.1002/ejoc.201403651ISI: 000351054500025OAI: oai:DiVA.org:kth-164466DiVA: diva2:806882
Funder
Swedish Research Council
Note

QC 20150422

Available from: 2015-04-22 Created: 2015-04-17 Last updated: 2017-12-04Bibliographically approved

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Franzén, Johan

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