Automated Serendipity with Self-Optimizing Continuous-Flow Reactors

Zacharias Amara, Emilia S. Streng, Ryan A. Skilton, Jing Jin, Michael W. George, Martyn Poliakoff

Research output: Journal PublicationArticlepeer-review

35 Citations (Scopus)

Abstract

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 γ-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. Self-optimizing continuous-flow reactors have been used to investigate the reaction of aniline with THF and DMC. High-selectivity profiles were obtained for the synthesis of methylated anilines or N-phenylpyrrolidines. By combining the three components in a single reaction system, a tandem alkylation reactivity leading to diversely alkylated anilines was discovered.

Original languageEnglish
Pages (from-to)6141-6145
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number28
DOIs
Publication statusPublished - 1 Oct 2015

Keywords

  • Acid-base catalysis
  • Alkylation
  • Aniline
  • Flow chemistry
  • Self-optimization
  • Supercritical fluids

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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