Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2022 Jan 25;27(3):772.
doi: 10.3390/molecules27030772.

Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions

Qing Huang  1 , Xiangjun Peng  2 , Hong Li  1 , Haiping He  2 , Liangxian Liu  1
Affiliations

Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions

Qing Huang et al. Molecules. .

Abstract

An efficient and general method for the synthesis of 3-sulfenylindoles and 3-selenylindoles employing visible-light irradiation with graphene oxide as a promoter at room temperature has been achieved. The reaction features are high yields, simple operation, metal-free and iodine-free conditions, an easy-to-handle oxidant, and gram-scalable synthesis. This simple protocol allows one to access a wide range of 3-arylthioindoles, 3-arylselenylindoles, and even 3-thiocyanatoindoles with good to excellent yields.

Keywords: graphene oxide; indole; selenylindole; sulfenylindole; visible-light.

PubMed Disclaimer

Conflict of interest statement

The authors declare that they have no conflict of interest.

Figures

Figure 1
Figure 1
Selected examples of biologically active 3-selanyl- and 3-sulfanylindole compounds.
Scheme 1
Scheme 1
C3 chalcogenylation of indoles.
Scheme 2
Scheme 2
Heterocyclic thiols and potassium thiocyanate used as C3 sulfenylation of indoles.
Scheme 3
Scheme 3
Synthesis of 3-selenylindoles. Reaction conditions: 4 (0.3 mmol), 8 (0.36 mmol), GO (50 wt %), and DCE (1 mL), for 8 h at rt under open air. Isolated yield.
Scheme 4
Scheme 4
Scale-up reaction between 4a and 5a.
Scheme 5
Scheme 5
Control experiments.
Scheme 6
Scheme 6
The proposed mechanism for the reaction.
See this image and copyright information in PMC

References

    1. Mellah M., Voituriez A., Schulz E. Chiral sulfur ligands for asymmetric catalysis. Chem. Rev. 2007;107:5133–5209. doi: 10.1021/cr068440h. - DOI - PubMed
    1. Feng M., Tang B., Liang S., Jiang X. Sulfur containing scaffolds in drugs: Synthesis and application in medicinal chemistry. Curr. Top. Med. Chem. 2016;16:1200–1216. doi: 10.2174/1568026615666150915111741. - DOI - PMC - PubMed
    1. Jarrett J.T. The biosynthesis of thiol- and thioether-containing cofactors and secondary metabolites catalyzed by radical S-adenosylmethionine enzymes. J. Biol. Chem. 2015;290:3972–3979. doi: 10.1074/jbc.R114.599308. - DOI - PMC - PubMed
    1. Ostrovidov S., Franck P., Joseph D., Martarello L., Kirsch G., Belleville F., Nabet P., Dousset B. Screening of new antioxidant molecules using flow cytometry. J. Med. Chem. 2000;43:1762–1769. doi: 10.1021/jm991019j. - DOI - PubMed
    1. Ninomiya M., Garud D.R., Koketsu M. Biologically significant selenium-containing heterocycles. Coord. Chem. Rev. 2011;255:2968–2990. doi: 10.1016/j.ccr.2011.07.009. - DOI

LinkOut - more resources