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Article Dans Une Revue Angewandte Chemie International Edition Année : 2019

An Original L-shape, Tunable N-Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis

Résumé

The synthesis and characterization of original NHC ligands based on an imidazo[1,5-a]pyridin-3-ylidene (IPy) scaffold functionalized with a flanking barbituric heterocycle is described as well as their use as tunable ligands for efficient gold-catalyzed C−N, C−O, and C−C bond formations. High activity, regio-, chemo-, and stereoselectivities are obtained for hydroelementation and domino processes, underlining the excellent performance (TONs and TOFs) of these IPy-based ligands in gold catalysis. The gold-catalyzed domino reactions of 1,6-enynes give rise to functionalized heterocycles in excellent isolated yields under mild conditions. The efficiency of the NHC gold 5Me complex is remarkable and mostly arises from a combination of steric protection and stabilization of the cationic AuI active species by ligand 1Me.
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Dates et versions

hal-02335228 , version 1 (05-11-2020)

Identifiants

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Yue Tang, Idir Benaissa, Mathieu Huynh, Laure Vendier, Noël Lugan, et al.. An Original L-shape, Tunable N-Heterocyclic Carbene Platform for Efficient Gold(I) Catalysis. Angewandte Chemie International Edition, 2019, 58 (24), pp.7977-7981. ⟨10.1002/anie.201901090⟩. ⟨hal-02335228⟩
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