Issue 3, 2020

A more sustainable and highly practicable synthesis of aliphatic isocyanides

Abstract

Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.

Graphical abstract: A more sustainable and highly practicable synthesis of aliphatic isocyanides

Supplementary files

Article information

Article type
Paper
Submitted
27 nov 2019
Accepted
16 jan 2020
First published
16 jan 2020
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2020,22, 933-941

A more sustainable and highly practicable synthesis of aliphatic isocyanides

K. A. Waibel, R. Nickisch, N. Möhl, R. Seim and M. A. R. Meier, Green Chem., 2020, 22, 933 DOI: 10.1039/C9GC04070F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements