Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 8, Pages 1834-1839Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403651
Keywords
Organocatalysis; Metathesis; Carbocations; Ketones; Alkenes
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Funding
- Swedish Research Council (VR)
- Stenbacks Foundation
- Royal Swedish Academy of Sciences
- Lars Hierta Memorial Foundation
- Wenner-Gren Foundation
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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.
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