Remy RDepartment of Chemistry, University of Fribourg , Chemin du Musée 9, CH-1700 Fribourg, Switzerland.
Bochet CGDepartment of Chemistry, University of Fribourg , Chemin du Musée 9, CH-1700 Fribourg, Switzerland.
2016-06-25
Published in:
Chemical reviews. - 2016
English
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.