Development and Scale-Up of a Novel Photochemical C–N Oxidative Coupling

A visible light promoted C–N-coupling of a functionalized pyridazinone with veratrole was developed to forge the central C–N bond of an agrochemical intermediate. Dosing aqueous NaOCl and 4% O2 in N2 under blue light irradiation (460 nm) was key to promote the desired transformation while generating...

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Bibliographic Details
Published in:Organic process research & development 2021-10, Vol.25 (10), p.2205-2220
Main Authors: Robinson, Alan, Dieckmann, Michael, Krieger, Jean-Philippe, Vent-Schmidt, Thomas, Marantelli, Dominique, Kohlbrenner, Ralf, Gribkov, Denis, Simon, Levente L, Austrup, David, Rod, Alexandre, Bochet, Christian G
Format: Article
Language:English
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Summary:A visible light promoted C–N-coupling of a functionalized pyridazinone with veratrole was developed to forge the central C–N bond of an agrochemical intermediate. Dosing aqueous NaOCl and 4% O2 in N2 under blue light irradiation (460 nm) was key to promote the desired transformation while generating benign wastes. Mechanistic studies suggest the formation of a N-chloro species that undergoes selective coupling via a radical pathway induced by the combination of light and oxygen. Further development led to an optimized semi-batch process, which was successfully scaled up to an initial 20 L and then 1.2 m3.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.1c00244