A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO2 extrusion followed by insertion of isothiocyanates

Asif Noor; Jiawei Li; George N. Khairallah; Zhen Li; Hossein Ghari; Allan J. Canty; Alireza Ariafard; Paul S. Donnelly; Richard A. J. O'Hair

doi:10.1039/C7CC00865A

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A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO₂ extrusion followed by insertion of isothiocyanates†

Asif Noor,^a Jiawei Li,^a George N. Khairallah,^a Zhen Li,^a Hossein Ghari,^b Allan J. Canty,

^c Alireza Ariafard,

*^b Paul S. Donnelly

*^a and Richard A. J. O'Hair

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Melbourne, Victoria 3010, Australia
E-mail: pauld@unimelb.edu.au, rohair@unimelb.edu.au

^b Department of Chemistry, Faculty of Science, Central Tehran Branch, Islamic Azad University, Shahrak Gharb, Tehran, Iran
E-mail: ariafard@yahoo.com

^c School of Physical Sciences, University of Tasmania, Hobart, Tasmania 7001, Australia

Abstract

A new palladium mediated “one pot” synthesis of thioamides from aromatic carboxylic acids (ArCO₂H + RNCS → ArC(S)NHR + CO₂) was discovered by gas-phase experiments and theoretical studies. Palladium-mediated decarboxylation of aromatic carboxylic acids followed by addition of substituted isothiocyanates leads to the corresponding thioamide derivatives.

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DOI: https://doi.org/10.1039/C7CC00865A
Article type: Communication
Submitted: 02 Feb 2017
Accepted: 10 Mar 2017
First published: 10 Mar 2017
This article is Open Access

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Chem. Commun., 2017,53, 3854-3857

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A one-pot route to thioamides discovered by gas-phase studies: palladium-mediated CO₂ extrusion followed by insertion of isothiocyanates

A. Noor, J. Li, G. N. Khairallah, Z. Li, H. Ghari, A. J. Canty, A. Ariafard, P. S. Donnelly and R. A. J. O'Hair, Chem. Commun., 2017, 53, 3854 DOI: 10.1039/C7CC00865A

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