Kloepfer, Viktor and Eckl, Robert and Floss, Johannes and Roth, Philippe M. C. and Reiser, Oliver and Barham, Joshua P. (2021) Catalyst-free, scalable heterocyclic flow photocyclopropanation. GREEN CHEMISTRY, 23 (17). pp. 6366-6372. ISSN 1463-9262, 1463-9270
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Industrial process development is driven by several factors, including safety, cost, robustness and environmental aspects. However, attempts to establish aryl diazo esters - which are highly valued in academic research for their reactivity as carbene precursors - in the chemical industry have been limited by their explosivity and toxicity. Their catalyst-free photolysis in continuous flow improves safety, sustainability and scalability compared to batch reactions. Herein, we report the continuous flow catalyst-free photocyclopropanation of heterocycles in up to grams per h productivity in a non-chlorinated, biodegradable solvent. Highly-functionalized cyclopropanated products are key intermediates in the synthesis of drugs and pharmaceutically-relevant compounds. Optimal conditions and process understanding were obtained by a Design of Experiments approach. In comparison with a large scale batch experiment, continuous flow conditions improved yield, productivity and process safety.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ACCEPTOR-SUBSTITUTED CYCLOPROPANES; TAMING HAZARDOUS CHEMISTRY; DIAZO-COMPOUNDS; LIGHT; OPTIMIZATION; FURANS |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Jul 2022 07:10 |
| Last Modified: | 05 Jul 2022 07:10 |
| URI: | https://pred.uni-regensburg.de/id/eprint/46205 |
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