Organic Letters
Organic Letters
5 years ago

Synthesis of Donor/Acceptor-Substituted Diazo Compounds in Flow and Their Application in Enantioselective Dirhodium-Catalyzed Cyclopropanation and C–H Functionalization

Synthesis of Donor/Acceptor-Substituted Diazo Compounds in Flow and Their Application in Enantioselective Dirhodium-Catalyzed Cyclopropanation and C–H Functionalization
Christopher W. Jones, Huw M. L. Davies, Chun-Jae Yoo, Daniel Rackl
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01073

DOI: 10.1021/acs.orglett.7b01073

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