Addition of N-H bonds to iridium: Synthesis and characterization of N-Ir-H complexes and the observation that an iridium N-bonded indole ring becomes activated for Michael addition to alkynes

Folami T. Ladipo, Joseph S. Merola

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The thermal reaction between the electron-rich iridium complex, [IrCOD(PMe3)3]Cl, 1a, and pyrrolic or anilinic N-H bonds results in the oxidative addition of the N-H bond and the formation of an amido iridium hydride complex, HIr(amido)(Cl)(PMe3)3 with loss of COD. The only isomer formed in this reaction has a meridional arrangement of PMe3 ligands, with H trans to Cl and the amido group trans to PMe3. The reaction products of 1a with pyrrole, indole and 3-methyl indole were fully characterized included by single crystal X-ray diffraction. Attachment of the pyrrolic ring nitrogen to the iridium results in an electron rich ring system that is activated and adds to alkynes in a Michael addition reaction under mild conditions without a catalyst.

Original languageEnglish
Pages (from-to)131-138
Number of pages8
JournalPolyhedron
Volume90
DOIs
StatePublished - Apr 18 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

  • Indole
  • Iridium
  • Michael addition
  • NH activation
  • Oxidative addition

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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