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Lepori, Mattia ; Dey, Indrasish ; Pratley, Cassie ; Barham, Joshua P.

Merging New and Old Concepts: Tandem Oxidative Radical‐Polar Crossover Ritter Amidation via Multicomponent Photo‐ and Electrochemical Processes

Lepori, Mattia , Dey, Indrasish , Pratley, Cassie and Barham, Joshua P. (2024) Merging New and Old Concepts: Tandem Oxidative Radical‐Polar Crossover Ritter Amidation via Multicomponent Photo‐ and Electrochemical Processes. European Journal of Organic Chemistry, e202400840.

Date of publication of this fulltext: 11 Dec 2024 05:49
Article
DOI to cite this document: 10.5283/epub.59763


Abstract

Nitrogen-containing drug molecules and pharmaceuticals are ubiquitous, rendering the construction of C−N bonds a crucial target in methodology development. The Ritter reaction is a well-established method for accessing C−N bonds by generating amide functionality through the reaction of carbocations and nitriles. Since its discovery back in 1948, the Ritter reaction has progressively advanced ...

Nitrogen-containing drug molecules and pharmaceuticals are ubiquitous, rendering the construction of C−N bonds a crucial target in methodology development. The Ritter reaction is a well-established method for accessing C−N bonds by generating amide functionality through the reaction of carbocations and nitriles. Since its discovery back in 1948, the Ritter reaction has progressively advanced towards milder and more sustainable conditions for carbocation generation. In this regard, notable contributions have been made by means of single electron transfer (SET) chemistry. Nowadays, photo- and electrochemistry are established methods of choice for the generation of reactive radical intermediates and their subsequent oxidation via radical-polar crossover (RPC) mechanism. We review recent examples of tandem RPC and Ritter-type protocols, demonstrating how photo- and electrochemical energies have been effectively harvested to expand the precursor pool for the Ritter reaction as well as reimagining the process with novel mechanisms and additives.



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Details

Item typeArticle
Journal or Publication TitleEuropean Journal of Organic Chemistry
Publisher:Wiley
Page Range:e202400840
Date18 September 2024
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie
Identification Number
ValueType
10.1002/ejoc.202400840DOI
KeywordsAmination · Radical polar crossover · Single electron transfer · Ritter reaction · Amidation
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-597635
Item ID59763

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