Journal ArticleDOI
Fluorine Transfer to Alkyl Radicals
Montserrat Rueda-Becerril,Claire Chatalova Sazepin,Joe C. T. Leung,Tulin Okbinoglu,Pierre Kennepohl,Jean-François Paquin,Glenn M. Sammis +6 more
TLDR
A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alKYl radicals, and calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media.Abstract:
The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F– or F+). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F•). A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals. This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom-stabilized radicals. Furthermore, calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations...read more
Citations
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Journal ArticleDOI
Introduction of Fluorine and Fluorine-Containing Functional Groups
TL;DR: This Review gives a brief summary of conventional fluorination reactions, including those reactions that introduce fluorinated functional groups, and focuses on modern developments in the field.
Journal ArticleDOI
Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
TL;DR: This Review compares classical and photocatalytic procedures for selected classes of reactions and highlights their advantages and limitations.
Journal ArticleDOI
Monofluorination of Organic Compounds: 10 Years of Innovation.
Pier Alexandre Champagne,Justine Desroches,Jean Denys Hamel,Mathilde Vandamme,Jean-François Paquin +4 more
Journal ArticleDOI
Visible-Light-Induced Decarboxylative Functionalization of Carboxylic Acids and Their Derivatives
TL;DR: Recent advances in visible-light-induced radical decarboxylative functionalization of carboxylic acids and their derivatives are discussed herein.
Journal ArticleDOI
Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins
TL;DR: A mechanistic framework for understanding this compendium of radical reactions is provided, covering the development of the field and contributions to reaction invention, mechanism, and application to complex molecule synthesis.
References
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Journal ArticleDOI
Fluorine in Pharmaceuticals: Looking Beyond Intuition.
TL;DR: Experimental progress in exploration of the specific influence of carbon-fluorine single bonds on docking interactions is reviewed and complementary analysis based on comprehensive searches in the Cambridge Structural Database and the Protein Data Bank is added.
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Fluorine in medicinal chemistry.
TL;DR: This tutorial review provides a sampling of renowned fluorinated drugs and their mode of action with a discussion clarifying the role and impact of fluorine substitution on drug potency.
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Chirality-Sensing Supramolecular Systems
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Fluorination in Medicinal Chemistry: Methods, Strategies, and Recent Developments
TL;DR: Methods for introducing fluorine into organic molecules are reviewed, with an emphasis on preparation of compounds designed for biomedicinal applications.