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. 2011 Sep 12;50(38):8900-3.
doi: 10.1002/anie.201104652. Epub 2011 Aug 11.

Accelerating palladium-catalyzed C-F bond formation: use of a microflow packed-bed reactor

Timothy Noël  1 , Thomas J Maimone, Stephen L Buchwald
Affiliations

Accelerating palladium-catalyzed C-F bond formation: use of a microflow packed-bed reactor

Timothy Noël et al. Angew Chem Int Ed Engl. .

Abstract

A flow process for Pd-catalyzed carbon fluorine bond formation is described. A microreactor using a packed-bed design allows for easy handling of large quantities of insoluble CsF with precise control over reaction times, efficient mixing, and the ability to safely handle elevated temperatures and pressures. A variety of aryl triflates, including heteroaryl ones, were converted to their corresponding aryl fluoride in short reaction times that would be difficult to achieve in a typical batch process.

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Figures

Figure 1
Figure 1
Conversion dependence on CsF loading in batch.
Figure 2
Figure 2
Schematic representation of the microreactor setup for the fluorination of aryl triflates in flow.
Figure 3
Figure 3
Pd-catalyzed fluorination of 1-naphthyltriflate in flow: (a) Catalyst loading and residence time comparison at 110 °C. (b) Temperature dependence with low catalyst loading (1.25 mol % Pd, 20 minute residence time).
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