Influence of bulky yet flexible <i>N</i>-heterocyclic carbene ligands in gold catalysis

Collado, Alba; Patrick, Scott R.; Gasperini, Danila; Meiries, Sébastien; Nolan, Steven P.

doi:10.3762/bjoc.11.196

Cited by 15 publications

(17 citation statements)

References 58 publications

(40 reference statements)

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“…Some other recent relevant examples of large yet flexible NHC ligands were reported by Nolan and co-workers 267,268 (Pd, for Suzuki−Miyaura and Buchwald−Hartwig reactions; Au, for alkyne hydration, nitrile hydration, and synthesis of homoallylic ketones) and Mauduit and co-workers 269 (Ru, for olefin metathesis).…”

Section: Hemilabile and Conformationally Labile N-heterocyclic Carben...mentioning

confidence: 97%

Smart N-Heterocyclic Carbene Ligands in Catalysis

2017

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It is well-recognized that N-heterocyclic carbene (NHC) ligands have provided a new dimension to the design of homogeneous catalysts. Part of the success of this type of ligands resides in the limitless access to a variety of topologies with tuned electronic properties, but also in the ability of a family of NHCs that are able to adapt their properties to the specific requirements of individual catalytic transformations. The term "smart" is used here to refer to switchable, multifunctional, adaptable, or tunable ligands and, in general, to all those ligands that are able to modify their steric or electronic properties to fulfill the requirements of a defined catalytic reaction. The purpose of this review is to comprehensively describe all types of smart NHC ligands by focusing attention on the catalytically relevant ligand-based reactivity.

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Section: Hemilabile and Conformationally Labile N-heterocyclic Carben...mentioning

confidence: 97%

Smart N-Heterocyclic Carbene Ligands in Catalysis

2017

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“…Known as ITent ("tentacular") ligands, [28] thesew ered eveloped by the Nolan group as as terically flexible class of ligandsf or Pd-catalysed Suzuki-Miyaura and Buchwald-Hartwig coupling reactions, [28,29] Ru-catalysed olefin metathesis reactions, [30] and gold-catalysed transformations. [31] In this study,w ew ill describe the first preparation as well as the first catalytic applicationo fITe nt-Ag-carboxylate complexes.…”

Section: Introductionmentioning

confidence: 99%

“…The study was performed in a systematic way, by varying the carboxylate ligand (including acetate and benzoates), and by introduction of a homologous series of bulky, yet flexible, imidazolium NHC ligands ( I Pr, I Pent, I Hept, and I Non). Known as I Tent (“tentacular”) ligands, these were developed by the Nolan group as a sterically flexible class of ligands for Pd‐catalysed Suzuki–Miyaura and Buchwald–Hartwig coupling reactions, Ru‐catalysed olefin metathesis reactions, and gold‐catalysed transformations . In this study, we will describe the first preparation as well as the first catalytic application of I Tent–Ag–carboxylate complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure and Catalytic Activity of NHC–Ag^I Carboxylate Complexes

Wong

Vummaleti

Cavallo

et al. 2016

Chemistry A European J

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A general synthetic route was used to prepare 15 new N-heterocyclic carbene (NHC)-Ag(I) complexes bearing anionic carboxylate ligands [Ag(NHC)(O2 CR)], including a homologous series of complexes of sterically flexible ITent ligands, which permit a systematic spectroscopic and theoretical study of the structural and electronic features of these compounds. The complexes displayed a significant ligand-accelerated effect in the intramolecular cyclisation of propargylic amides to oxazolidines. The substrate scope is highly complementary to that previously achieved by NHC-Au and pyridyl-Ag(I) complexes.

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“…This effect is negligible from IHept to INon, where the extra carbon atoms are too far from the metal center to exert a strong effect (Figure 8). 121 The corresponding [Au(ITent)-NTf 2 ] (NHCs-14−16) complexes were prepared, and their catalytic activity was evaluated and compared to that of [Au(IPr)NTf 2 ], in the hydration of phenylacetylene and 4methoxybenzonitrile, and in the synthesis of homoallylic ketones from diphenylacetylene and allyl alcohol. In all cases, the [Au(ITent)NTf 2 ] complexes were less active than [Au-(IPr)NTf 2 ] affording lower conversions.…”

Section: N-heterocyclic Carbene Ligandsmentioning

confidence: 99%

“…In the case of nitrile hydration and the synthesis of homoallylic ketones, a detrimental effect of the length increase was found, with IPent being the most efficient ligand. 121 3.1.2. N-Aryl NHC Derivatives.…”

Section: N-heterocyclic Carbene Ligandsmentioning

confidence: 99%