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DOI: 10.1055/a-2283-6798
Transformation of Benzaldehydes to Benzonitriles via Cyanophosphates without One-Carbon Homologation
This work was financially supported by research funds from Osaka Medical and Pharmaceutical University (OMPU).
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Abstract
The transformation of benzaldehydes into benzonitriles via cyanophosphates (CPs) with tetrabutylammonium azide (Bu4N·N3) was found to afford a range of benzonitriles in modest-to-high yields. As the CN-carbon of benzonitriles arises from the formyl-carbon of benzaldehydes, this is a new type of CP-reaction, distinctly different from the past one-carbon nitrile homologation. In contrast, the reaction of ketone- or aliphatic aldehyde-CPs with Bu4N·N3 resulted in mono-deethylaton forming tetrabutylammonium salts.
Key words
cyanophosphate - tetrabutylammonium azide - mono-deethylaton - benzonitrile - tetrabutylammonium saltSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2283-6798.
- Supporting Information
Publication History
Received: 14 February 2024
Accepted after revision: 07 March 2024
Accepted Manuscript online:
07 March 2024
Article published online:
20 March 2024
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