Synthesis of unsymmetrically substituted triarylamines via acceptorless dehydrogenative aromatization using a Pd/C and p -toluenesulfonic acid hybrid relay catalyst

An efficient and convenient procedure for synthesizing triarylamines based on a dehydrogenative aromatization strategy has been developed. A hybrid relay catalyst comprising carbon-supported Pd (Pd/C) and p -toluenesulfonic acid (TsOH) was found to be effective for synthesizing a variety of triaryla...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-03, Vol.11 (16), p.4074-4084
Main Authors: Takayama, Satoshi, Yatabe, Takafumi, Koizumi, Yu, Jin, Xiongjie, Nozaki, Kyoko, Mizuno, Noritaka, Yamaguchi, Kazuya
Format: Article
Language:English
Subjects:
Amines
Aniline
Aromatic compounds
Catalysts
Chemistry
Cyclohexanone
Dehydrogenation
Imines
Nanoparticles
Organic compounds
Palladium
Relay
Synthesis
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Summary:An efficient and convenient procedure for synthesizing triarylamines based on a dehydrogenative aromatization strategy has been developed. A hybrid relay catalyst comprising carbon-supported Pd (Pd/C) and p -toluenesulfonic acid (TsOH) was found to be effective for synthesizing a variety of triarylamines bearing different aryl groups starting from arylamines (diarylamines or anilines), using cyclohexanones as the arylation sources under acceptorless conditions with the release of gaseous H 2 . The proposed reaction comprises the following relay steps: condensation of arylamines and cyclohexanones to produce imines or enamines, dehydrogenative aromatization of the imines or enamines over Pd nanoparticles (NPs), and elimination of H 2 from the Pd NPs. In this study, an interesting finding was obtained indicating that TsOH may promote the dehydrogenation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc06442g