Palladium-mediated fragmentation of meta photocycloadducts using carbon based electrophiles: Part 1

Penkett, Clive S, Sims, Rupert O, Byrne, Paul W, Kingston, Lee, French, Richard, Dray, Lauriane, Berritt, Simon, Lai, Jason, Avent, Anthony G and Hitchcock, Peter (2006) Palladium-mediated fragmentation of meta photocycloadducts using carbon based electrophiles: Part 1. Tetrahedron, 62 (14). pp. 3423-3434. ISSN 0040-4020

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Abstract

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.

Item Type: Article
Additional Information: CSP directed the work and is the corresponding author. Paper describes a unique tandem Heck arylation - fragmentation - allyl silane forming reaction involving a metaphotocycloadduct.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Clive Penkett
Date Deposited: 06 Feb 2012 18:40
Last Modified: 30 Nov 2012 17:00
URI: http://sro.sussex.ac.uk/id/eprint/17715
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