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Synthesis 2022; 54(13): 3077-3084
DOI: 10.1055/a-1770-8592
DOI: 10.1055/a-1770-8592
paper
Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source
Jinan University
Abstract
The present study describes the one-pot palladium-catalyzed cyanation of commercially available aryldiazonium tetrafluoroborate derivatives with 2-(piperidin-1-yl)acetonitrile (an organic cyano reagent) under mild conditions. This process utilizes a Pd/(Me3Si)2 system and is applied to a wide scope of aromatic diazonium substrates to give the corresponding nitrile-containing products in moderate to high yields (59–92%). This methodology is employed for the preparation of etravirine, a drug used for the treatment of HIV, and for transformations of 1H-indole-2-carbonitrile into compounds that are used as a NMDA receptor antagonists and that have high potential against mutant HIV strains. The mechanism proposed for this Pd-catalyzed cyanation involves cyanide ions, as confirmed using indicator paper.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1770-8592.
- Supporting Information
Publication History
Received: 30 December 2021
Accepted after revision: 14 February 2022
Accepted Manuscript online:
14 February 2022
Article published online:
25 April 2022
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For examples, see:
For selected examples of NaCN as a CN source, see:
For selected examples of KCN as a CN source, see:
For selected examples of Zn(CN)2 as a CN source, see:
For selected examples of Me3SiCN as a CN source, see:
For examples using ‘non-metallic’ CN sources, see:
For recent reviews on C–CN cleavage, see:
For indicator strategies, see: