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Synlett 2022; 33(14): 1383-1390
DOI: 10.1055/a-1809-7768
cluster
Organic Chemistry in Thailand

Brønsted Acidic Ionic Liquid Catalyzed Three-Component Friedel–Crafts Reaction for the Synthesis of Unsymmetrical Triarylmethanes

Suttida Rinkam
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Sangesook, Chonburi 20131, Thailand
,
Warapong Senapak
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Sangesook, Chonburi 20131, Thailand
,
Sarayut Watchasit
c   Nuclear Magnetic Resonance Spectroscopic Laboratory, Science Innovation Facility, Faculty of Science, Burapha University, Chonburi 20131, Thailand
,
Rungnapha Saeeng
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Sangesook, Chonburi 20131, Thailand
b   The Research Unit in Synthetic Compounds and Synthetic Analogues from Natural Product for Drug Discovery (RSND), Burapha University, Chonburi 20131, Thailand
,
Uthaiwan Sirion  ∗
a   Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Sangesook, Chonburi 20131, Thailand
b   The Research Unit in Synthetic Compounds and Synthetic Analogues from Natural Product for Drug Discovery (RSND), Burapha University, Chonburi 20131, Thailand
› Author AffiliationsThis work was financially supported by a Research Grant from Burapha University through the National Research Council of Thailand (Grant no. 162/2561), the Office of National Higher Education Science Research and Innovation Policy Council (NXPO) (Grant no. BO5F630030), the Center of Excellence for Innovation in Chemistry (PERCH-CIC) and the Research Unit in Synthetic Compounds and Synthetic Analogues from Natural Products for Drug Discovery (RSND), Burapha University. Special thanks to Dr. Ron Beckett, Faculty of Science, Burapha University for his comments and proofreading the English manuscript.
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Abstract

A convenient and practical method for the synthesis of unsymmetrical triarylmethanes was demonstrated through a one-pot three-component double Friedel–Crafts reaction of various aliphatic, aromatic, or heteroaromatic aldehydes with N,N-dialkylanilines and indoles by using a Brønsted acidic ionic liquid as the catalyst. This method was successfully applied under metal- and solvent-free conditions at 80 °C, affording the corresponding unsymmetrical triarylmethane products in moderate to high yields from a broad range of substrates. In addition, the mechanism of this reaction was studied by quantitative NMR analysis.

Key words

triarylmethanes - diarylmethylindoles - Friedel–Crafts reaction - Brønsted acid - ionic liquid - metal-free conditions

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1809-7768.
  • Supporting Information


Publication History

Received: 14 February 2022

Accepted after revision: 28 March 2022

Accepted Manuscript online:
28 March 2022

Article published online:
15 June 2022

© 2022. Thieme. All rights reserved

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