Issue 3, 2023
From the journal:

Organic & Biomolecular Chemistry

Complementary mechanochemical and biphasic approaches for the synthesis of organic thiocyanates using hexacyanoferrates as non-toxic cyanide sources†

Caroline Grundke,‡a   Jonathan Groß,‡a   Nina Vierengel,a   Jason Sirleaf,a   Matthias Schmitz, ORCID logo a   Leonie Kriegera  and  Till Opatz ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Johannes Gutenberg-University, Duesbergweg 10–14, 55128 Mainz, Germany
E-mail: opatz@uni-mainz.de

Abstract

Herein, we describe two complementary approaches towards various organic thiocyanates that are affordable, reliable and follow the principles of sustainable chemistry, starting from commercially available thiols or disulfides. Additionally, the application of this mild method to the first total synthesis of psammaplin B is demonstrated. Non-toxic and inexpensive ferricyanide is used as the cyanide source, which can be activated either in a mechanochemical, solvent-free approach, or in a biphasic solvent system allowing easier work-up. A total of 27 examples is demonstrated, with up to quantitative yields.

Graphical abstract: Complementary mechanochemical and biphasic approaches for the synthesis of organic thiocyanates using hexacyanoferrates as non-toxic cyanide sources

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Article information

DOI
https://doi.org/10.1039/D2OB02216H
Article type
Paper
Submitted
04 Dec 2022
Accepted
19 Dec 2022
First published
19 Dec 2022

Org. Biomol. Chem., 2023,21, 644-650

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Complementary mechanochemical and biphasic approaches for the synthesis of organic thiocyanates using hexacyanoferrates as non-toxic cyanide sources

C. Grundke, J. Groß, N. Vierengel, J. Sirleaf, M. Schmitz, L. Krieger and T. Opatz, Org. Biomol. Chem., 2023, 21, 644 DOI: 10.1039/D2OB02216H

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