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Palladium-mediated fragmentation of meta photocycloadducts using carbon based electrophiles: Part 1
journal contribution
posted on 2023-06-07, 20:56 authored by Clive S Penkett, Rupert O Sims, Paul W Byrne, Lee Kingston, Richard French, Lauriane Dray, Simon Berritt, Jason Lai, Anthony G Avent, Peter HitchcockSubstituted benzene derived meta photocycloadducts have been shown to undergo a fragmentation/arylation reaction under Heck reaction conditions to give bridged bicyclo[3.2.1] compounds in a highly atom-efficient manner. When an anisole derived meta photocycloadduct is used, a bridgehead ketone is generated. However, if an alkylbenzene derived meta photocycloadduct is used, a bridgehead alkene is formed. This strategy has been used to create novel enol ether and transient allyl silane compounds.
History
Publication status
- Published
Journal
TetrahedronISSN
0040-4020External DOI
Issue
14Volume
62Page range
3423-3434Pages
12.0Department affiliated with
- Chemistry Publications
Notes
CSP directed the work and is the corresponding author. Paper describes a unique tandem Heck arylation - fragmentation - allyl silane forming reaction involving a metaphotocycloadduct.Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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