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

Org Lett

Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO) , Universidad de Alicante , Apdo. 99 , 03080 Alicante , Spain.

Published: March 2019

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.

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Source
http://dx.doi.org/10.1021/acs.orglett.9b00064DOI Listing

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