Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 17, Pages 11104-11115Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00921
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Funding
- Fundamental Research Funds for the Central Universities [2018BLRD12]
- National Natural Science Foundation of China [21776020]
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Remote C-H functionalization at CS is the most sparingly observed selectivity in the functionalization of indole templates. Herein, we reported that the combination of a AgSbF6 catalyst and phenyliodine diacetate oxidation enabled the C-H selenylation at the CS position of indole scaffolds in a selective version, thus leading to the formation of a wide scope of 5-selenylated indole derivatives, which are otherwise difficult to prepare. Mechanistic studies indicated that current transformation follows a radical process, and the tethered C3 pivaloyl group on indole scaffolds plays roles in both blocking the active C3 position and manipulating the electronic affinity of the arenes.
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