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Martin Bundgaard Johansen

PhD Student

Martin Bundgaard Johansen
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Project title: Decarboxylative Trifluoromethylations Performed Safely using Continuous Flow – Flow Reactor Design and Scale-up

Main supervisor: Troels Skrydstrup

Co-supervisor: Anders Thyboe Lindhardt                 

Project period: Nov 2015 to Aug 2020

Research section: Biological and Chemical Engineering

Project description
The trifluoromethyl group (CF3) is an important functional group in drugs and agrochemical substances as it induces greater metabolic stability, perturbation of pKa values and effects changes in ground state conformations. The usage CF3-donors are limited to small-scale research and development purposes because they normally are highly specialized and expensive. Metallic trifluoroacetate-derivatives might be a potential CF3-donor in a decarboxylation reaction but current methods using these derivatives require super-stoichiometric use of copper(I)-mediator and elevated temperatures (140-200°C). Evolution of carbon dioxide at high temperatures might lead to hazardous situations and therefore calls for extraordinary measures in order to prevent run-away of the reaction and/or carbon dioxide production.

The main focus of this project will be to perform the synthesis of CF3-containing molecules using a metallic trifluoroacetate-derivative as CF3-donor and a catalytic amount of copper(I)-mediator in a closed continuous flow system, which offers several advantages compared to classical batch synthesis. Some of the advantages include excellent heat/cool transfer properties due to a high surface/volume ratio, short reaction times, complete pressure control, straightforward scale-up and, and most importantly, increased operator safety.

External partners/project that the Ph.D is part of
Cheminova A/S (Ib Winkelman)
Massachusetts Institute of Technology (Timothy F. Jamison)




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