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Arene–Alkene Cycloaddition

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Remy Richard, Bochet Christian G.,
Project Photons in organic synthesis
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Original article (peer-reviewed)

Journal Chemical Reviews
Volume (Issue) 116(17)
Page(s) 9816 - 9849
Title of proceedings Chemical Reviews
DOI 10.1021/acs.chemrev.6b00005


Cycloaddns. are among the most efficient chem. processes, combining atom economy, stereospecificity, and the ability to generate mol. complexity in a single step.  Arom. rings would in principle be ideal reaction partners, as they contain, at least from the topol. point of view, both olefinic and diene subunits; however, the stability of the conjugated arom. system would be broken by cycloaddn. reactions, which are therefore rarely applied, because kinetics and thermodn. hinder the process.  From that aspect, photochem. activation opens interesting perspectives, as one can selectively provide excess energy to one of the reactants but not to the product, thus preventing thermal back reaction.  Indeed, arom. rings show a rich photochem., ranging from isomerizations, substitutions, and addns. to cycloaddns.  In this review, we will focus on cycloaddns., covering literature from early observations up to the present.