Substrate-Controlled\nDivergent Reductive Cyclization\nof 2‑Arylanilines Using CO<sub>2</sub> as a Switching Reagent

Capturing CO<sub>2</sub> is highly valued in the field\nof organic\nsynthesis, especially underdeveloped dual-CO<sub>2</sub> conversion.\nIn this study, we detail a novel reductive cyclization of 2-indolylanilines\nwith dual CO<sub>2</sub> as a difunctional reagent in the presence\nof PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted\nquinoxalines. Furthermore, another chemoselective cyclization with\n2-pyrrolylanilines is also realized by converting mono-CO<sub>2</sub>. Mechanistic investigations shed light upon the fact that this substrate-controlled\ndivergence mainly depends on the formation of <i>N</i>-diacylative\nintermediates.

Publication Details

Journal
Figshare
Published
2024-12-30
DOI
https://doi.org/10.1021/acs.orglett.4c04538.s001
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
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article

Substrate-Controlled\nDivergent Reductive Cyclization\nof 2‑Arylanilines Using CO2 as a Switching Reagent

Figshare
Carbon dioxide utilization in catalysis
article

Substrate-Controlled\nDivergent Reductive Cyclization\nof 2‑Arylanilines Using CO2 as a Switching Reagent

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Abstract

Capturing CO<sub>2</sub> is highly valued in the field\nof organic\nsynthesis, especially underdeveloped dual-CO<sub>2</sub> conversion.\nIn this study, we detail a novel reductive cyclization of 2-indolylanilines\nwith dual CO<sub>2</sub> as a difunctional reagent in the presence\nof PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted\nquinoxalines. Furthermore, another chemoselective cyclization with\n2-pyrrolylanilines is also realized by converting mono-CO<sub>2</sub>. Mechanistic investigations shed light upon the fact that this substrate-controlled\ndivergence mainly depends on the formation of <i>N</i>-diacylative\nintermediates.

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Carbon dioxide utilization in catalysis
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