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Synthesis of Donor/Acceptor-Substituted Diazo Compounds in Flow and Their Application in Enantioselective Dirhodium-Catalyzed Cyclopropanation and C–H Functionalization
- Rackl, Daniel, Yoo, Chun-Jae, Jones, Christopher W., Davies, Huw M. L.
- Organic letters 2017 v.19 no.12 pp. 3055-3058
- carbon-hydrogen bond activation, chemical reactions, chemical structure, diazo compounds, enantioselectivity, potassium, sieves, sodium, thiosulfates
- A tandem reaction system has been developed for the preparation of donor/acceptor-substituted diazo compounds in continuous flow coupled to dirhodium-catalyzed C–H functionalization or cyclopropanation. Hydrazones were oxidized in flow by solid-supported N-iodo-p-toluenesulfonamide potassium salt (PS-SO₂NIK) to generate the diazo compounds, which were then purified by passing through a column of molecular sieves/sodium thiosulfate.