Photochemical Synthesis of Succinic Ester-Containing Phenanthridines from Diazo Compounds as 1,4-Dicarbonyl Precursors

We disclosed herein a straightforward photochemical method for the construction of phenanthridines containing a synthetically useful succinate unit. The reaction occurred under visible-light irradiation with cheap eosin Y Na as photoredox catalyst and a diazo compound as the succinate precursor. Und...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (32), p.6018-6023
Main Authors: Ye, Hai-Bing, Zhou, Xu-Yu, Li, Lei, He, Xiang-Kui, Xuan, Jun
Format: Article
Language:English
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Summary:We disclosed herein a straightforward photochemical method for the construction of phenanthridines containing a synthetically useful succinate unit. The reaction occurred under visible-light irradiation with cheap eosin Y Na as photoredox catalyst and a diazo compound as the succinate precursor. Under the optimal reaction conditions, a wide range of phenanthridines were obtained in moderate to good yields. Note that the succinate units in the final heterocycles could be easily transformed into many valuable structures, such as γ-butyrolactone, dihydrofuran-2­(3H)-one, and tetrahydrofuran. Mechanistic experiments were performed to support the proposed mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02313