Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 25, Pages 7161-7165Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703369
Keywords
arylation; C-H activation; copper; hypervalent compounds; flow chemistry
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Funding
- Dutch Science Foundation (NWO) by an ECHO grant [713.013.001]
- VIDI grant [14150]
- COST (European Cooperation in Science and Technology) Action [CA15106]
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Described herein is an effective and practical modular flow design for the meta-selective C-H arylation of anilines. The design consists of four continuous-flow modules (i.e., diaryliodonium salt synthesis, meta-selective C-H arylation, inline copper extraction, and aniline deprotection) which can be operated either individually or consecutively to provide direct access to meta-arylated anilines. With a total residence time of 1 hour, the desired product could be obtained in high yield and excellent purity without the need for column chromatography, and the residual copper content meets the standards for parenterally administered pharmaceutical substances.
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