Three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling?
Organic & Biomolecular Chemistry Pub Date: 2017-07-24 DOI: 10.1039/C7OB01547J
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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