Iron(II) Chloride–1,1′-Binaphthyl-2,2′-diamine (FeCl₂–BINAM) Complex Catalyzed Domino Synthesis of Bisindolylmethanes from Indoles and Primary Alcohols

Abstract

Biologically important bisindolylmethanes are synthesized in a domino fashion by using an iron(II) chloride–(±)-1,1′-binaphthyl-2,2′-diamine [FeCl₂–(±)-BINAM] complex as the catalyst. This method proceeds via oxidation of a primary alcohol into the corresponding aldehyde followed by nucleophilic addition of an indole in the presence of the catalyst. A reaction intermediate is synthesized separately and converted into the bisindolylmethane product under the same reaction conditions as support for the proposed mechanism.

Key words

bisindolylmethanes - iron catalysts - alcohol oxidation - domino reactions - BINAM ligand

• References

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Domino reactions have attracted a great deal of attention because they provide a high degree of molecular complexity from structurally simple molecules. These reactions are typically economic and more environmentally friendly as they avoid the isolation of unstable intermediates and reduce production costs. See:
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