Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis
| Autor: | Jose C. Gonzalez‐Gomez, Burkhard König, Nieves P. Ramirez |
|---|---|
| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Nuevos Materiales y Catalizadores (MATCAT) |
| Rok vydání: | 2019 |
| Předmět: |
Riboflavin tetraacetate
010405 organic chemistry Decarboxylation Chemistry Radical Organic Chemistry Decarboxylative cyanation Flavin group Visible-light flavin photocatalysis Cyanation 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Química Orgánica Photocatalysis Physical and Theoretical Chemistry Aliphatic carboxylic acids Visible spectrum |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| ISSN: | 1523-7052 |
| Popis: | An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions. This work was generously supported by the Spanish Ministerio de Economía y Competitividad (No. CTQ2017-88171-P), the Generalitat Valenciana (No. AICO/2017/007) and the Deutsche Forschungsgemeinschaft (Nos. GRK 1626, KO1537/18-1). N.P.R. thanks the EDUA for a mobility grant and Instituto de Síntesis Orgánica for financial support. |
| Databáze: | OpenAIRE |
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