Acyl Radical Chemistry via Visible-Light Photoredox Catalysis
Top Cited Papers
- 12 December 2018
- journal article
- review article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 51 (02), 303-333
- https://doi.org/10.1055/s-0037-1610329
Abstract
‡ These authors contributed equally to this work. Visible-light photoredox catalysis enables easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-keto acids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes the recent progress on visible-light-driven acyl radical generation using transition-metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts. 1 Introduction 2 The Scope of This Review 3 Aldehydes as a Source of Acyl Radicals 4 α-Keto Acids as a Source of Acyl Radicals 5 Carboxylic Acids as a Source of Acyl Radicals 6 Anhydrides as a Source of Acyl Radicals 7 Acyl Thioesters as a Source of Acyl Radicals 8 Acyl Chlorides as a Source of Acyl Radicals 9 Acyl Silanes as a Source of Acyl Radicals 10 Conclusions and Future OutlookKeywords
Funding Information
- National Institute of General Medical Sciences (R35GM119652)
This publication has 96 references indexed in Scilit:
- Organocatalytic umpolung: N-heterocyclic carbenes and beyondChemical Society Reviews, 2012
- Palladium‐Catalyzed Decarboxylative C-H Bond Arylation of ThiophenesAngewandte Chemie, 2011
- Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and HydroperoxidesJournal of the American Chemical Society, 2011
- Mechanism of the Catalytic Deperoxidation of tert‐Butylhydroperoxide with Cobalt(II) AcetylacetonateChemistry – A European Journal, 2010
- Stereospecific Decarboxylative Allylation of SulfonesJournal of the American Chemical Society, 2010
- Mechanism of Base Activation of PersulfateEnvironmental Science & Technology, 2010
- Low‐Temperature Ag/Pd‐Catalyzed Decarboxylative Cross‐Coupling of Aryl Triflates with Aromatic Carboxylate SaltsChemistry – A European Journal, 2010
- Addition of Benzoyl Radicals to Butyl Acrylate: Absolute Rate Constants by Time-Resolved EPRMacromolecules, 2005
- Determination of the C4-H Bond Dissociation Energies of NADH Models and Their Radical Cations in AcetonitrileChemistry – A European Journal, 2003
- Gas-Phase and Solution-Phase Homolytic Bond Dissociation Energies of H−N+ Bonds in the Conjugate Acids of Nitrogen BasesThe Journal of Organic Chemistry, 1996