Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO<sub>2</sub> as a Switching Reagent

Capturing CO<sub>2</sub> is highly valued in the field of organic synthesis, especially underdeveloped dual-CO<sub>2</sub> conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO<sub>2</sub> as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO<sub>2</sub>. Mechanistic investigations shed light upon the fact that this substrate-controlled divergence mainly depends on the formation of <i>N</i>-diacylative intermediates.

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Publication Details

Journal
Organic Letters
Published
2024-12-30
DOI
https://doi.org/10.1021/acs.orglett.4c04538
Citations
5
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
Field-Weighted Citation Impact
0.89

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article

Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO2 as a Switching Reagent

Chengyuan Liang, Qiang Yan, Jiang Nan, Lanxin Zhu et al.
5 citations
Organic Letters
Carbon dioxide utilization in catalysis
0.89
article

Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO2 as a Switching Reagent

Chengyuan Liang, Qiang Yan, Jiang Nan, Lanxin Zhu, Chen Zhang, Shilei Liu, Rui Cao
article en
5 citations

Abstract

Capturing CO<sub>2</sub> is highly valued in the field of organic synthesis, especially underdeveloped dual-CO<sub>2</sub> conversion. In this study, we detail a novel reductive cyclization of 2-indolylanilines with dual CO<sub>2</sub> as a difunctional reagent in the presence of PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective cyclization with 2-pyrrolylanilines is also realized by converting mono-CO<sub>2</sub>. Mechanistic investigations shed light upon the fact that this substrate-controlled divergence mainly depends on the formation of <i>N</i>-diacylative intermediates.

Organic LettersVol. 27(1)
Shaanxi University of Science and Technology (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 32%
Carbon dioxide utilization in catalysis
0.89
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