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Arene-Alkene Cycloaddition.

Type of publication Peer-reviewed
Publikationsform Review article (peer-reviewed)
Publication date 2016
Author Remy Richard, Bochet Christian G,
Project Photons in organic synthesis
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Review article (peer-reviewed)

Journal Chemical reviews
Volume (Issue) .(.)
Page(s) . - .
Title of proceedings Chemical reviews
DOI 10.1021/acs.chemrev.6b00005


Cycloadditions are among the most efficient chemical processes, combining atom economy, stereospecificity, and the ability to generate molecular complexity in a single step. Aromatic rings would in principle be ideal reaction partners, as they contain, at least from the topological point of view, both olefinic and diene subunits; however, the stability of the conjugated aromatic system would be broken by cycloaddition reactions, which are therefore rarely applied, because kinetics and thermodynamics hinder the process. From that aspect, photochemical 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, aromatic rings show a rich photochemistry, ranging from isomerizations, substitutions, and additions to cycloadditions. In this review, we will focus on cycloadditions, covering literature from early observations up to the present.