Efficient synthesis of aryldipyrromethanes in water and their application in the synthesis of corroles and dipyrromethenes

Taoufik Rohand, Eduard Dolusic, Thien H. Ngo, Wouter Maes, Wim Dehaen

Research output: Contribution to journalArticle

Abstract

In this paper, we describe the efficient and selective synthesis of aryldipyrromethanes in aqueous medium by acid-catalyzed (HCl) condensations of aromatic aldehydes with 3 equivalents of pyrrole at room temperature. The precipitated aryldipyrromethanes can be isolated directly from the reaction mixture in an essentially pure state by simple filtration. Time control seems to be essential to avoid significant formation of the tripyrromethane analogue and the reaction time is strongly dependent on the nature of the aromatic aldehyde. A one-pot synthesis of several aryldipyrromethenes and various novel meso-aryl-substituted trans-A2B-corroles was also achieved starting from the obtained aryldipyrromethanes. Trichloroacetic acid was the preferred acid catalyst for the preparation of meso-triarylcorroles from the condensation of 5-(2,6-dichlorophenyl)dipyrromethane with more reactive aldehydes, while trifluoroacetic acid was preferred for less reactive substrates.
Original languageEnglish
Pages (from-to)307-324
Number of pages18
JournalARKIVOC
Volume2007
Issue numberx
Publication statusPublished - 2007

Fingerprint

Aldehydes
Water
Condensation
Trifluoroacetic Acid
Trichloroacetic Acid
Pyrroles
Acids
Catalysts
Substrates
dipyrromethene
corrole
Temperature
dipyrromethane

Keywords

  • Condensation in water
  • dipyrromethenes
  • N-alkylation
  • trans-A2B-corroles
  • dipyrromethanes

Cite this

Rohand, Taoufik ; Dolusic, Eduard ; Ngo, Thien H. ; Maes, Wouter ; Dehaen, Wim. / Efficient synthesis of aryldipyrromethanes in water and their application in the synthesis of corroles and dipyrromethenes. In: ARKIVOC. 2007 ; Vol. 2007, No. x. pp. 307-324.
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Efficient synthesis of aryldipyrromethanes in water and their application in the synthesis of corroles and dipyrromethenes. / Rohand, Taoufik; Dolusic, Eduard; Ngo, Thien H.; Maes, Wouter; Dehaen, Wim.

In: ARKIVOC, Vol. 2007, No. x, 2007, p. 307-324.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Efficient synthesis of aryldipyrromethanes in water and their application in the synthesis of corroles and dipyrromethenes

AU - Rohand, Taoufik

AU - Dolusic, Eduard

AU - Ngo, Thien H.

AU - Maes, Wouter

AU - Dehaen, Wim

PY - 2007

Y1 - 2007

N2 - In this paper, we describe the efficient and selective synthesis of aryldipyrromethanes in aqueous medium by acid-catalyzed (HCl) condensations of aromatic aldehydes with 3 equivalents of pyrrole at room temperature. The precipitated aryldipyrromethanes can be isolated directly from the reaction mixture in an essentially pure state by simple filtration. Time control seems to be essential to avoid significant formation of the tripyrromethane analogue and the reaction time is strongly dependent on the nature of the aromatic aldehyde. A one-pot synthesis of several aryldipyrromethenes and various novel meso-aryl-substituted trans-A2B-corroles was also achieved starting from the obtained aryldipyrromethanes. Trichloroacetic acid was the preferred acid catalyst for the preparation of meso-triarylcorroles from the condensation of 5-(2,6-dichlorophenyl)dipyrromethane with more reactive aldehydes, while trifluoroacetic acid was preferred for less reactive substrates.

AB - In this paper, we describe the efficient and selective synthesis of aryldipyrromethanes in aqueous medium by acid-catalyzed (HCl) condensations of aromatic aldehydes with 3 equivalents of pyrrole at room temperature. The precipitated aryldipyrromethanes can be isolated directly from the reaction mixture in an essentially pure state by simple filtration. Time control seems to be essential to avoid significant formation of the tripyrromethane analogue and the reaction time is strongly dependent on the nature of the aromatic aldehyde. A one-pot synthesis of several aryldipyrromethenes and various novel meso-aryl-substituted trans-A2B-corroles was also achieved starting from the obtained aryldipyrromethanes. Trichloroacetic acid was the preferred acid catalyst for the preparation of meso-triarylcorroles from the condensation of 5-(2,6-dichlorophenyl)dipyrromethane with more reactive aldehydes, while trifluoroacetic acid was preferred for less reactive substrates.

KW - Condensation in water

KW - dipyrromethenes

KW - N-alkylation

KW - trans-A2B-corroles

KW - dipyrromethanes

M3 - Article

VL - 2007

SP - 307

EP - 324

JO - ARKIVOC

JF - ARKIVOC

SN - 1551-7004

IS - x

ER -