Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings

Linglin Wu, Emma Drinkel, Fiona Gaggia, Samanta Capolicchio, Anthony Linden, Laura Falivene, Luigi Cavallo, Reto Dorta*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

Abstract

Into the groove: The introduction of a C 2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl.

Original languageEnglish (US)
Pages (from-to)12886-12890
Number of pages5
JournalChemistry - A European Journal
Volume17
Issue number46
DOIs
StatePublished - Nov 11 2011

Keywords

  • N-heterocyclic carbene ligand
  • biaryls
  • cross-coupling
  • palladium

ASJC Scopus subject areas

  • Chemistry(all)

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