Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis

Sebastien Michel Bernard Meiries, Gaetan Romain Le Duc, Anthony Raymond Georges Chartoire, Alba Collado-Martinez, Klaus Speck, Kasun Sankalpa Athukorala Arachchige, Alexandra Martha Zoya Slawin, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

91 Citations (Scopus)

Abstract

A straightforward and scalable eight-step synthesis of new N-het-
ACHTUNGTRENUNGeroACHTUNGTRENUNGcyclic carbenes (NHCs) has been
developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent
(“Tent” for “tentacular”) of which the well-known IMes (N,N’-bis(2,4,6-tri-
methylphenyl)imidazol-2-ylidene), IPr (N,N’-bis(2,6-i(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N’-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent
family: IPent (N,N’-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N’-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene) and INon (N,N’-bis(2,6-di(5-nonyl)phenyl)imidazol-2-ylidene). The electronic and steric properties of
each NHC were studied through the preparation of both nickel and palladium
complexes. Finally the effect of these new ITent ligands in Pd-catalyzed
Suzuki–Miyaura and Buchwald–Hartwig cross-couplings was investigated.
Original languageEnglish
Pages (from-to)17358-17368
Number of pages11
JournalChemistry - A European Journal
Volume19
Early online date14 Nov 2013
DOIs
Publication statusPublished - 2013

Keywords

  • Bulky, catalysis, flexible, N-heterocyclic carbene, palladium, tentacular

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