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. 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.

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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

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