Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 11, Pages 1628-1636Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100006
Keywords
Continuous flow; Gel-bound catalysts; Microfluidic reactor; Organocatalysis; Synthetic methods
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Funding
- Kunststofftechnik Paderborn (KTP)
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In this study, a new synthetic pathway for azoxybenzenes with different substitution patterns was developed using a microfluidic reactor with gel-bound proline organocatalysts. The effects of different functionalities on conversion, yield, and reaction times were analyzed in detail by NMR, and the turnover number and turnover frequency were determined.
In the search for a new synthetic pathway for azoxybenzenes with different substitution patterns, an approach using a microfluidic reactor with gel-bound proline organocatalysts under continuous flow is presented. Herein the formation of differently substituted azoxybezenes by reductive dimerization of nitrosobenzenes within minutes at mild conditions in good to almost quantitative yields is described. The conversion within the microfluidic reactor is analyzed and used for optimizing and validating different parameters. The effects of the different functionalities on conversion, yield, and reaction times are analyzed in detail by NMR. The applicability of this reductive dimerization is demonstrated for a wide range of differently substituted nitrosobenzenes. The effects of these different functionalities on the structure of the obtained azoxyarenes are analyzed in detail by NMR and single-crystal X-ray diffraction. Based on these results, the turnover number and the turnover frequency were determined.
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