Rhodium-Catalyzed C–H Arylation of Indoles with Arylsilanes at Room Temperature

The Cp*Rh-catalyzed C-H arylation of indoles with arylsilanes is developed. This C-H activation transformation allows for the Rh-catalyzed indole C<sub>2</sub> arylation to overcome the limitations of requiring strong directing group assistance and high-temperature conditions, achieving a room-temperature transformation driven by a weak directing group. Cp*Rh/MeOH catalytic media are considered a key factor enabling this transformation to occur under mild conditions, and experimental studies and theoretical calculations were performed to rationalize the reaction mechanisms and the influence of methanol as a solvent in promoting the reaction.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-06
DOI
https://doi.org/10.1021/acs.joc.4c01549
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.50

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article

Rhodium-Catalyzed C–H Arylation of Indoles with Arylsilanes at Room Temperature

Yi Dong, Tingting Hou, Heng Xu, Guang Li et al.
2 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.50
article

Rhodium-Catalyzed C–H Arylation of Indoles with Arylsilanes at Room Temperature

Yi Dong, Tingting Hou, Heng Xu, Guang Li, Xin Yang, Deyu Wu, Xin Wang
article en
2 citations

Abstract

The Cp*Rh-catalyzed C-H arylation of indoles with arylsilanes is developed. This C-H activation transformation allows for the Rh-catalyzed indole C<sub>2</sub> arylation to overcome the limitations of requiring strong directing group assistance and high-temperature conditions, achieving a room-temperature transformation driven by a weak directing group. Cp*Rh/MeOH catalytic media are considered a key factor enabling this transformation to occur under mild conditions, and experimental studies and theoretical calculations were performed to rationalize the reaction mechanisms and the influence of methanol as a solvent in promoting the reaction.

The Journal of Organic ChemistryVol. 89(22)
Chinese Academy of Medical Sciences & Peking Union Medical College (CN)
Chinese Academy of Medical Sciences
Openalex Percentile: Top 38%
Catalytic C–H Functionalization Methods
0.50
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