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Direct Organocatalytic Oxo-Metathesis, a trans-Selective Carbocation-Catalyzed Olefination of Aldehydes
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.ORCID-id: 0000-0003-1933-4193
2015 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 8, s. 1834-1839Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2015. nr 8, s. 1834-1839
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URN: urn:nbn:se:kth:diva-164466DOI: 10.1002/ejoc.201403651ISI: 000351054500025OAI: oai:DiVA.org:kth-164466DiVA, id: diva2:806882
Forskningsfinansiär
Swedish Research Council
Merknad

QC 20150422

Tilgjengelig fra: 2015-04-22 Laget: 2015-04-17 Sist oppdatert: 2017-12-04bibliografisk kontrollert

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