Novel Methodology for the Efficient Synthesis of 3-Aryloxindoles: [1,2]-Phospha-Brook Rearrangement-Palladium-Catalyzed Cross-Coupling Sequence

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Abstract

A novel methodology for the efficient synthesis of 3-aryloxindoles from isatin derivatives was developed. The methodology involves the formation of an oxindole having a phosphate moiety at the C-3 position via the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis followed by palladium-catalyzed cross-coupling with aryl boron reagents. The one-pot synthesis of 3-aryloxindoles from isatin derivatives is also described.

Original languageEnglish
Article numberst-2016-u0165-l
Pages (from-to)1848-1853
Number of pages6
JournalSynlett
Volume27
Issue number12
DOIs
Publication statusPublished - 2016 Jul 21

Keywords

  • Bronsted base catalysis
  • cross-coupling
  • oxindole derivatives
  • palladium catalyst
  • phospha-Brook rearrangement

ASJC Scopus subject areas

  • Organic Chemistry

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