Recent topics of iridium-catalyzed hydrosilylation of tertiary amides to silylhemiaminals

Atsushi Tahara, Hideo Nagashima

Research output: Contribution to journalReview articlepeer-review

5 Citations (Scopus)

Abstract

Iridium-catalyzed hydrosilylation of amides with 1,1,3,3-tetramethyldisiloxane (TMDS) allows access to silylhemiaminals, which are often spontaneously converted to aldenamines. Iridium(I) phosphine species generated from IrCl(CO)(PPh3)2, IrCl(PPh3)3, or a mixture of [IrCl(COD)]2 and phosphorous ligands showed high catalytic activity for this reaction protocol, which demonstrated remarkable compatibility toward other reducible functional groups such as ketone and ester groups. This reaction enables the synthesis of π-conjugate enamines having hole-transport properties by appropriate selection of the iridium catalyst. Easy access to silyl hemiaminals and enamined stimulated other research groups to discover new reductive C–C bond-forming reactions to transform amides to amine derivatives, which can be applied to the synthesis of complex alkaloid molecules.

Original languageEnglish
Article number151423
JournalTetrahedron Letters
Volume61
Issue number4
DOIs
Publication statusPublished - 2020 Jan 23
Externally publishedYes

Keywords

  • Enamine
  • Hydrosilylation
  • Iridium catalysts
  • Silylhemiaminal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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