Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation

Herein, we report a selective reductive rearrangement of substituted quinolines into indoles-a privileged structural motif widely found in natural products and bioactive molecules. This quinoline skeletal editing is accomplished through water activation mediated by photocatalytically generated phosphine radical cations. The developed protocol provides a robust and broadly applicable approach for synthesizing diverse indole derivatives from readily available quinoline substrates.

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Publication Details

Journal
Chemical Science
Published
2025-12-22
DOI
https://doi.org/10.1039/d5sc08793g
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation

Nico Spreckelmeyer, Elena Sophia Horst, Jieun Kim, Jingjing Zhang et al.
Chemical Science
Catalytic C–H Functionalization Methods
article

Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation

Nico Spreckelmeyer, Elena Sophia Horst, Jieun Kim, Jingjing Zhang, Armido Studer, Lammert Jessika
article en

Abstract

Herein, we report a selective reductive rearrangement of substituted quinolines into indoles-a privileged structural motif widely found in natural products and bioactive molecules. This quinoline skeletal editing is accomplished through water activation mediated by photocatalytically generated phosphine radical cations. The developed protocol provides a robust and broadly applicable approach for synthesizing diverse indole derivatives from readily available quinoline substrates.

Chemical ScienceVol. 17(7)
University of Münster (DE)
National Research Foundation, Deutsche Forschungsgemeinschaft, National Research Foundation of Korea, Westfälische Wilhelms-Universität Münster
Clean water and sanitation
Openalex Percentile: Top 34%
Catalytic C–H Functionalization Methods
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