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Issue 31, 2017
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Three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling

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Abstract

We report a facile three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline, with the first step featuring Pd/dihydroxyterphenylphosphine (DHTP)-catalyzed ortho-selective Sonogashira coupling followed by cyclization to afford 2-substituted 5,7-dichloroindoles. Subsequent introduction of aryl or alkenyl groups at the C7 position was achieved by Pd/DHTP-catalyzed site-selective Kumada–Tamao–Corriu coupling, with further substitution of the chlorine at the C5 position (Suzuki–Miyaura coupling or Buchwald–Hartwig amination) affording 2,5,7-trisubstituted indoles.

Graphical abstract: Three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling

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Article information


Submitted
26 Jun 2017
Accepted
22 Jul 2017
First published
24 Jul 2017

Org. Biomol. Chem., 2017,15, 6645-6655
Article type
Paper

Three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling

M. Yamaguchi and K. Manabe, Org. Biomol. Chem., 2017, 15, 6645
DOI: 10.1039/C7OB01547J

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