Photocycloadditions of benzene derivatives and their systematic application to organic synthesis
Arthur Desvals A and Norbert Hoffmann
A *
+ Author Affiliations
- Author Affiliations
A CNRS, Université de Reims Champagne-Ardenne, ICMR, Equipe de Photochimie, UFR Sciences, B.P. 1039, 51687 Reims, France.
Arthur Desvals obtained his bachelor’s degree in 2017 from the University of Versailles Saint-Quentin-en-Yvelines and his master’s degree in 2019 from the University Paris-Saclay. He then received his PhD degree in 2023 under the supervision of Dr Norbert Hoffmann at the Reims Institute of Molecular Chemistry. His research focuses on photochemical reactions and valorisation of compounds derived from biomass. |
Norbert Hoffmann studied chemistry at the RWTH Aachen University, Germany and received his PhD degree in 1992 under the supervision of Hans-Dieter Scharf. In 1993, he obtained a permanent position (Chargé de Recherche) at the French National Centre for Scientific Research (CNRS) in Reims, France. In 2004, he was appointed Research Director in the CNRS. His main research interests are in the field of organic photochemistry: electron transfer, photoinduced radical reactions, stereoselective reactions, cycloadditions of aromatic compounds, reactions in photochemical continuous flow reactors and application of these reactions to organic synthesis. Further research interests concern the production of fine chemicals from biomass and the synthesis and characterisation of dyes (chemistry of polymethine and perylene derivatives). |
Australian Journal of Chemistry 76(3) 117-129 https://doi.org/10.1071/CH23029
Submitted: 10 February 2023 Accepted: 20 March 2023 Published: 4 May 2023
© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
Photocycloadditions of benzene derivatives with alkenes play an important role as key steps in organic synthesis. Intramolecular reactions have been most frequently studied in this context. Often, meta or [2 + 3] photocycloadditions take place in competition with ortho or [2 + 2] additions. The influence of the substitution pattern and the spin multiplicity of the excited state on the outcome of these reactions is discussed. A topological analysis permitting a systematic application of the [2 + 3] photocycloadditions to the total synthesis of natural products is presented and a selection of corresponding syntheses is discussed. More recently the [2 + 2] photocycloaddition and consecutive rearrangements on organic synthesis have been published. Some approaches in the context of asymmetric synthesis have also been reported.
Keywords: aromatic compounds, meta or [2 + 3] photocyloaddition, molecular complexity, natural products, ortho or [2 + 2] photocycloaddition, photocycloaddition, spin multiplicity, terpenes, total synthesis.
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