Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

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Title: Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis
Authors: Ramírez, Nieves P. | König, Burkhard | Gonzalez-Gomez, Jose C.
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Decarboxylative cyanation | Aliphatic carboxylic acids | Visible-light flavin photocatalysis
Knowledge Area: Química Orgánica
Issue Date: 20-Feb-2019
Publisher: American Chemical Society
Citation: Organic Letters. 2019, 21(5): 1368-1373. doi:10.1021/acs.orglett.9b00064
Abstract: 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.
Sponsor: 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.
ISSN: 1523-7060 (Print) | 1523-7052 (Online)
DOI: 10.1021/acs.orglett.9b00064
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 American Chemical Society
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas

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