Synthesis of Arylamides via Ritter-Type Cleavage of Solid-Supported Aryltriazenes.

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ID: 1471
2019
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Abstract
A novel route for the synthesis of N-arylamides via the cleavage of aryltriazenes with alkyl or aryl nitriles is presented. We developed a variation of the Ritter reaction that allows the use of acetonitrile as solvent and reagent in reactions with solid-supported precursors. The reaction was optimized for the generation of N-aryl acetamides using a diverse range of immobilized building blocks including o-, m-, and p-substituted aryltriazenes. The cleavage via the Ritter-type conversion was combined with an on-bead cross-coupling reaction of halogen-substituted aryltriazenes with pyrazoles. Additionally, the synthesis of on-bead generated arylboronic ester-substituted triazenes was shown. The developed procedure was further expanded to use other commercially available nitriles, such as acrylonitrile, benzonitrile, and chlorinated alkyl nitriles as suitable reagents for a Ritter-type cleavage of the prepared triazene linkers.
Reference Key
wippert2019synthesis Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Wippert, Nicolai A;Jung, Nicole;Bräse, Stefan;
Journal acs combinatorial science
Year 2019
DOI
10.1021/acscombsci.9b00096
URL
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