Issue 2, 2024

A cyanide-free synthesis of nitriles exploiting flow chemistry

Abstract

A continuous flow process for the synthesis of aryl nitriles in a cyanide-free manner is reported. Using a simple setup and mild conditions, TosMIC (p-tosylmethyl isocyanide) is used as a readily available precursor to convert ketones into nitriles via the van Leusen reaction. The resulting continuous process is fast (1.5 minutes residence time) and both the scalability (up to 8.8 g h−1) and reproducibility of this approach has been demonstrated for a variety of nitrile products. Through these studies, 4-tosyloxazole was isolated as a side-product that aids in understanding the mechanistic pathways of this transformation. Overall, this efficient flow method provides for a straightforward flow synthesis of nitrile-containing building blocks in high yields and with an improved safety profile.

Graphical abstract: A cyanide-free synthesis of nitriles exploiting flow chemistry

Supplementary files

Article information

Article type
Paper
Submitted
29 Aug 2023
Accepted
12 Oct 2023
First published
12 Oct 2023
This article is Open Access
Creative Commons BY-NC license

React. Chem. Eng., 2024,9, 349-354

A cyanide-free synthesis of nitriles exploiting flow chemistry

N. Disney, M. Smyth, S. Wharry, T. S. Moody and M. Baumann, React. Chem. Eng., 2024, 9, 349 DOI: 10.1039/D3RE00458A

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