Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α, β-unsaturated ketones

Byron J. Truscott, George C. Fortman, Alexandra M. Z. Slawin, Steven P. Nolan

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

The synthesis and catalytic activity of three well-defined monomeric rhodium(I) hydroxide complexes bearing N-heterocyclic carbene (NHC) ligands are reported. [Rh(cod)(ICy)(OH)] promoted the 1,4-addition of arylboronic acids to cyclic enones, with TONs and TOFs of 100,000 and 6,600 h-1, respectively, at 0.001 mol% catalyst loadings. Mechanistic studies permitted the isolation of a phenylrhodium intermediate.
Original languageEnglish
Pages (from-to)7038-7041
Number of pages4
JournalOrganic & Biomolecular Chemistry
Volume9
Issue number20
Early online date22 Aug 2011
DOIs
Publication statusPublished - 2011

Keywords

  • CATALYZED ASYMMETRIC 1,4-ADDITION
  • CROSS-COUPLING REACTION
  • CHIRAL DIENE LIGANDS
  • CARBONYL-COMPOUNDS
  • 7,7'-DISUBSTITUTED BINAPS
  • PHENYLBORONIC ACID
  • ROOM-TEMPERATURE
  • RHODIUM CATALYST
  • HIGH-PERFORMANCE
  • ENONES

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