Abstract
Transition metal catalyzed carbon-carbon bond formation reactions have become important transformations in organic synthesis. In this study, we have explored a general strategy of transition metal free carbocatalytic carbon–hydrogen (C–H) functionalization. A carbon-based catalyst bearing nitrogen functional groups can facilitate the C–H functionalization of unactivated arenes to obtain biaryl products. We propose the active sites on the catalyst by analyzing its chemical composition before and after reaction, in-situ FT-IR, in-situ electron spin resonance (ESR), and density function theory calculation. As a result, stable NH groups and radicals were found to be effective for the reaction, providing high recyclability of the catalyst. The present methodology offers a diverse substrate scope without any dry or inert conditions, thus opening the door for an alternative to the conventional metal-based coupling reactions.
| Original language | English |
|---|---|
| Pages (from-to) | 344-350 |
| Number of pages | 7 |
| Journal | Journal of Catalysis |
| Volume | 365 |
| DOIs | |
| Publication status | Published - Sep 1 2018 |
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Keywords
- Carbocatalysis
- Cross-coupling reaction
- Graphene
- Nitrogen functional group
- Radical
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
Cite this
Investigation of active sites for C–H functionalization on carbon-based catalyst : Effect of nitrogen-containing functional groups and radicals. / Sohail Ahmad, Muhammad; Suzuki, Hideyuki; Wang, Chen; Zhao, Min; Nishina, Yuta.
In: Journal of Catalysis, Vol. 365, 01.09.2018, p. 344-350.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Investigation of active sites for C–H functionalization on carbon-based catalyst
T2 - Effect of nitrogen-containing functional groups and radicals
AU - Sohail Ahmad, Muhammad
AU - Suzuki, Hideyuki
AU - Wang, Chen
AU - Zhao, Min
AU - Nishina, Yuta
PY - 2018/9/1
Y1 - 2018/9/1
N2 - Transition metal catalyzed carbon-carbon bond formation reactions have become important transformations in organic synthesis. In this study, we have explored a general strategy of transition metal free carbocatalytic carbon–hydrogen (C–H) functionalization. A carbon-based catalyst bearing nitrogen functional groups can facilitate the C–H functionalization of unactivated arenes to obtain biaryl products. We propose the active sites on the catalyst by analyzing its chemical composition before and after reaction, in-situ FT-IR, in-situ electron spin resonance (ESR), and density function theory calculation. As a result, stable NH groups and radicals were found to be effective for the reaction, providing high recyclability of the catalyst. The present methodology offers a diverse substrate scope without any dry or inert conditions, thus opening the door for an alternative to the conventional metal-based coupling reactions.
AB - Transition metal catalyzed carbon-carbon bond formation reactions have become important transformations in organic synthesis. In this study, we have explored a general strategy of transition metal free carbocatalytic carbon–hydrogen (C–H) functionalization. A carbon-based catalyst bearing nitrogen functional groups can facilitate the C–H functionalization of unactivated arenes to obtain biaryl products. We propose the active sites on the catalyst by analyzing its chemical composition before and after reaction, in-situ FT-IR, in-situ electron spin resonance (ESR), and density function theory calculation. As a result, stable NH groups and radicals were found to be effective for the reaction, providing high recyclability of the catalyst. The present methodology offers a diverse substrate scope without any dry or inert conditions, thus opening the door for an alternative to the conventional metal-based coupling reactions.
KW - Carbocatalysis
KW - Cross-coupling reaction
KW - Graphene
KW - Nitrogen functional group
KW - Radical
UR - http://www.scopus.com/inward/record.url?scp=85050378592&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85050378592&partnerID=8YFLogxK
U2 - 10.1016/j.jcat.2018.07.013
DO - 10.1016/j.jcat.2018.07.013
M3 - Article
VL - 365
SP - 344
EP - 350
JO - Journal of Catalysis
JF - Journal of Catalysis
SN - 0021-9517
ER -