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Issue 20, 2018
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Modular synthesis of heptaarylindole

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Abstract

The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide key ynamide intermediates. Subsequent inverse electron-demand intramolecular [4 + 2] cycloaddition furnished pentaarylindoles (PAIs) regioselectively. This strategy was also applied to the synthesis of tetraarylazaindole with four different aryl substituents. PAIs underwent further arylations at the C2- and N1-positions, providing HAI with seven different aryl substituents with virtually complete regioselectivity.

Graphical abstract: Modular synthesis of heptaarylindole

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Article information


Submitted
28 Apr 2018
Accepted
03 May 2018
First published
03 May 2018

Org. Biomol. Chem., 2018,16, 3771-3776
Article type
Paper

Modular synthesis of heptaarylindole

S. Suzuki, T. Asako, K. Itami and J. Yamaguchi, Org. Biomol. Chem., 2018, 16, 3771
DOI: 10.1039/C8OB00993G

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