A Bisphosphonic Acid as a Heterogeneous Organocatalyst for the Synthesis of Bis(indolyl)methanes

Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, University of Birjand

2 Department of Chemistry, Faculty of Science, University of Birjand, Birjand, 97179-414 Iran.

Abstract

1,4-Piperazinediylbis(methylene) bisphosphonic acid as Brønsted acid organocatalyst was prepared and effectively catalyzed Friedel-Crafts addition of indoles to aromatic aldehydes and α, β-unsaturated carbonyl compounds in ethanol. All reaction products were characterized with 1HNMR technique. The synthesis of bis(indolyl)methanes was successfully achieved by a one pot three component reaction of various aromatic aldehydes with indole using H4L as a heterogeneous Brønsted acid organocatalyst. Also, the same catalytic system has produced 3-substituted indoles with 1,4 addition Michael reaction in excellent yields. This catalytic system has an extensive substrate domain, and is eco-friendly and cost effective. Green solvent heterogeneous reaction condition, metal-free catalyst, simple workup procedure, reasonable reaction time, excellent yield of products and reusability of the catalyst are the advantages of the protocol. To show the competency of H4L catalytic system in comparison with other Brønsted acids catalysts towards the synthesis of 3,3ʹ-bisindolyl(4-chlorophenyl) methane, some of the previous results have been presented. Examination of the results shows the supremacy of title protocol for synthesis of Bis(indolyl)methanes and 3-substituted indoles in terms of reaction times, yields, the catalyst loading, and conditions used.

Graphical Abstract

A Bisphosphonic Acid as a Heterogeneous Organocatalyst for the Synthesis of Bis(indolyl)methanes

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Iranian Journal of Chemistry
Volume 1, Issue 1 - Serial Number 1
January 2019
Pages 39-46

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History

  • Receive Date: 27 May 2018
  • Revise Date: 13 September 2018
  • Accept Date: 24 September 2018

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