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 AJ O'Hair

Journal article

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 AJ O'Hair

Chemical Communications | Royal Society of Chemistry | Published : 2017

DOI: 10.1039/c7cc00865a

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.

University of Melbourne Researchers

George Khairallah Author Chemistry

Richard O'Hair Author Chemistry

Asif Noor Author Chemistry

Paul Donnelly Author Chemistry

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

We acknowledge: Financial support from Australian Research Council (DP1096134 (GNK), DP120101540 (AJC), DP150101388 (AJC, RAJO), DP160100288 and FT130100204 (PSD), computing time from the University of Tasmania and National Computing Infrastructure, Profs. Marisa Kozlowski, Craig Hutton and Jon Tunge for useful discussions and Mr Yang Yang for experimental assistance.