<i>p</i>-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-<i>b</i>]indoles

5,10-Dihydroindeno[1,2-<i>b</i>]indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented <i>p</i>-TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp<sup>2</sup>)-CN/C(sp<sup>2</sup>)-H coupling, offering a series of 5,10-dihydroindeno[1,2-<i>b</i>]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.

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Publication Details

Journal
Organic Letters
Published
2024-08-05
DOI
https://doi.org/10.1021/acs.orglett.4c02051
Citations
4
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.94

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article

p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

Anurag Verma, Nayan Ghosh, Ruchir Kant
4 citations
Organic Letters
Chemical Synthesis and Analysis
0.94
article

p-TsOH-Mediated Intramolecular C2-Arylation on NH-Indoles: Access of 5,10-Dihydroindeno[1,2-b]indoles

Anurag Verma, Nayan Ghosh, Ruchir Kant
article en
4 citations

Abstract

5,10-Dihydroindeno[1,2-<i>b</i>]indole has served as an important starting precursor for BARAC-fluor reagent in medicinal chemistry. Herein, an unprecedented <i>p</i>-TsOH assisted intramolecular C2-arylation of NH-indoles via C(sp<sup>2</sup>)-CN/C(sp<sup>2</sup>)-H coupling, offering a series of 5,10-dihydroindeno[1,2-<i>b</i>]indoles with moderate to good yields, has been showcased under redox-neutral conditions. Furthermore, successful scalability and synthetic applications highlight the practical nature of the method.

Organic LettersVol. 26(32)
Central Drug Research Institute (IN), Academy of Scientific and Innovative Research (IN)
University Grants Commission, Science and Engineering Research Board
Openalex Percentile: Top 26%
Chemical Synthesis and Analysis
0.94
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