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  4. The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide
 
research article

The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

Hulla, Martin  
•
Nussbaum, Simon  
•
Bonnin, Alexy R.
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November 11, 2019
Chemical Communications (ChemComm)

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the cyclization reaction is acid catalyzed. The mismatch in catalytic conditions means that only one of the steps can be catalyzed in a single pot reaction. While the N-formylation reaction is frequently the target of catalyst development, the cyclization reaction requires comparably much harsher reaction conditions. Identification of these difficulties lead us to the development of a one-pot, two-step synthesis of benzimidazole under mild reaction conditions employing acid catalysts.

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Type
research article
DOI
10.1039/c9cc06156h
Web of Science ID

WOS:000494428800005

Author(s)
Hulla, Martin  
Nussbaum, Simon  
Bonnin, Alexy R.
Dyson, Paul J.  
Date Issued

2019-11-11

Publisher

Royal Society of Chemistry

Published in
Chemical Communications (ChemComm)
Volume

55

Issue

87

Start page

13089

End page

13092

Subjects

Chemistry, Multidisciplinary

•

Chemistry

•

n-heterocyclic carbene

•

c1 building-block

•

reductive functionalization

•

co2

•

amines

•

formylation

•

methylation

•

hydrosilane

•

carboxylation

•

cyclization

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCOM  
Available on Infoscience
November 21, 2019
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/163296
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