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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 Hitchcock
Substituted 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

Tetrahedron

ISSN

0040-4020

Issue

14

Volume

62

Page range

3423-3434

Pages

12.0

Department 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

2012-02-06

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