Continuous Flow Synthesis of Difluoroamine Systems by Direct Fluorination

Abstract

(2013) 'Continuous ow synthesis of diuoroamine systems by direct uorination.', Australian journal of chemistry., 66 (2). pp. 145-150. Further information on publisher's website:http://dx.doi.org/10.1071/CH12381Publisher's copyright statement: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractContinuous flow methodology for the synthesis of perfluoroaryl difluoroamine derivatives by reaction of fluorine gas with an appropriate perfluoroaniline substrate is described, further demonstrating the efficient use of flow regimes for reactions involving highly reactive and toxic reagents.

The Use of Gases in Flow Synthesis

“…63b The continuous flow direct fluorination of various anilines has been reported by the Sandford group to yield the corresponding N,N-difluoroaniline products, which were highlighted as being versatile starting materials for additional synthesis (Scheme 27). 64 A laminar flow reactor was used for these transformations to furnish the perfluoro products in moderate to good yields (54−71% yields, 4 examples). These were isolated in crude form after extraction with DCM and could be purified via silica chromatography.…”

“…Two step flow synthesis of 4-fluoro-3,5-dimethylpyrazole derivatives through direct fluorination of 1,3-dicarbonyl substrates.The continuous flow, direct fluorination, of various anilines has been reported by the Sandford group to yield the corresponding N,N-difluoroaniline products which were highlighted as versatile starting materials for additional synthesis (Scheme 27) 64. A laminar flow reactor was used for these transformations to furnish the perfluro products in moderate to good yields (54-71% yields, 4 examples).…”

Flow Chemistry: An Enabling Tool for Chemical Synthesis and Manufacture

“…Applications involving the safe generation of hazardous reagents or reactive intermediates in microreactors are reported herein. [10][11][12] Finally, it is particularly noteworthy to see the expansion of continuous flow methods to areas outside traditional organic synthesis. The synthesis and scale-up of functional polymers using multi-stage processes represents an exciting application of this key technology.…”