Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 28, Pages 6141-6145Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500980
Keywords
Self-optimization; Flow chemistry; Aniline; Alkylation; Acid-base catalysis; Supercritical fluids
Categories
Funding
- SYNFLOW
- Companhia Brasileira de Metalurgia e Mineracao (CBMM)
- SIN-CHEM [FPA 2013-0037]
- Royal Society
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A self-optimizing approach is used as a tool for targeting known and unknown materials in the continuous reaction of aniline, dimethyl carbonate (DMC) and tetrahydrofuran (THF) in supercritical CO2 on gamma-Al2O3. The study led to the formation of methylated anilines or carbamate derivatives and unusual addition products with THF including pyrrolidines and N-alkylated anilines. The identification of these products leads to the development of a plausible mechanism for the reactions. The system not only demonstrates a high flexibility that the self-optimization approach provides, including the ability to optimize for a variety of products by using a single catalyst, but also the ability to discover unexpected and original synthetic reactions.
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