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Palladium-mediated fragmentation reactions of meta photocycloadducts to afford arylated or oxidatively cyclised products
journal contribution
posted on 2023-06-08, 09:42 authored by Clive S Penkett, Rupert O Sims, Paul W Byrne, Simon Berritt, Lewis E Pennicott, Stephen P Rushton, Anthony G Avent, Peter B HitchcockWhilst seeking to improve the yield of a Heck-style arylation/fragmentation reaction using a silyloxy substituted meta photocycloadduct, an alternative reaction pathway was discovered that led to the formation of the unique oxidatively cyclised compound 8. This tricyclic ether is believed to form as the result of the meta photocycloadduct structure fragmenting to give a -allyl palladium species and then subsequently being displaced by a neighbouring hydroxyl group. An attempt to develop an enantioselective version of this reaction via the desymmetrisation of a meso -allyl palladium intermediate was made using the meta photocycloadduct derived from anisole and Z-but-2-ene-1,4-diol, however no enantioenrichment of the products could be detected.
History
Publication status
- Published
Journal
TetrahedronISSN
0040-4020Publisher
ElsevierExternal DOI
Issue
40Volume
62Page range
9403-9409Department affiliated with
- Chemistry Publications
Notes
(with Clive S. Penkett, Rupert O. Sims, Paul W. Byrne, Simon Berritt, Stephen P. Rushton, Anthony G. Avent and Peter B. Hitchcock)Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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