Impact of Adding <i>N</i>-hexylamine to Nickel Metallophotoredox C–N Coupling to Form Diarylamines

The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C-N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives to determine their effects on the synthesis of diarylamines in a flow photochemical system. Notably, <i>n</i>-hexylamine demonstrated the most significant promotional effect. Spectroscopic studies and experimental data reveal <i>n</i>-hexylamine substitutes DABCO as a Ni catalyst ligand, enhancing yields particularly in sterically hindered arylamines.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.joc.4c02106
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Impact of Adding N-hexylamine to Nickel Metallophotoredox C–N Coupling to Form Diarylamines

Fujun Li, A. A. Miskevich, Shengyang Tao, Wenbo Yang et al.
2 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
1.87
article

Impact of Adding N-hexylamine to Nickel Metallophotoredox C–N Coupling to Form Diarylamines

Fujun Li, A. A. Miskevich, Shengyang Tao, Wenbo Yang, Haiyang Wang, Lijing Zhang, Yuchao Wang, Valery A. Loiko
article en
2 citations

Abstract

The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C-N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives to determine their effects on the synthesis of diarylamines in a flow photochemical system. Notably, <i>n</i>-hexylamine demonstrated the most significant promotional effect. Spectroscopic studies and experimental data reveal <i>n</i>-hexylamine substitutes DABCO as a Ni catalyst ligand, enhancing yields particularly in sterically hindered arylamines.

The Journal of Organic ChemistryVol. 90(3)
National Academy of Sciences of Belarus (BY), Dalian University of Technology (CN), Dalian University (CN)
Belarusian Republican Foundation for Fundamental Research, Dalian High-Level Talent Innovation Program, National Natural Science Foundation of China, China Postdoctoral Science Foundation, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 18%
Radical Photochemical Reactions
1.87
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Impact of Adding <i>N</i>-hexylamine to Nickel Metallophotoredox C–N Coupling to Form Diarylamines — Fujun Li, A. A. Miskevich, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS