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
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI ( Science of Atomic Layers (SATL), Grant Number 16H00915 ) and JST SICORP .
Funding Information:
This work was financially supported by JSPS KAKENHI (Science of Atomic Layers (SATL), Grant Number 16H00915) and JST SICORP.
Publisher Copyright:
© 2018 Elsevier Inc.
PY - 2018/9
Y1 - 2018/9
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
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U2 - 10.1016/j.jcat.2018.07.013
DO - 10.1016/j.jcat.2018.07.013
M3 - Article
AN - SCOPUS:85050378592
VL - 365
SP - 344
EP - 350
JO - Journal of Catalysis
JF - Journal of Catalysis
SN - 0021-9517
ER -