Skeleton decoration of NHCs by amino groups and its sequential booster effect on the palladium-catalyzed buchwald–hartwig amination - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2014

Skeleton decoration of NHCs by amino groups and its sequential booster effect on the palladium-catalyzed buchwald–hartwig amination

Résumé

A challenging synthetic modification of PEPPSI-type palladium pre-catalysts consisting of a stepwise incorporation of one and two amino groups onto the NHC skeleton was seen to exert a sequential enhancement of the electronic donor properties. This appears to be positively correlated with the catalytic performances of the corresponding complexes in the Buchwald–Hartwig amination. This is illustrated, for example, by the quantitative amination of 4-chloroanisole by morpholine within 2 h at 25 °C with a 2 mol % catalyst/substrate ratio or by a significant reduction of catalytic loading (down to 0.005 mol %) for the coupling of aryl chlorides with anilines (max TON: 19 600).

Dates et versions

hal-02023184 , version 1 (18-02-2019)

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Y. Zhang, Vincent César, G. Storch, Noël Lugan, Guy Lavigne. Skeleton decoration of NHCs by amino groups and its sequential booster effect on the palladium-catalyzed buchwald–hartwig amination. Angewandte Chemie International Edition, 2014, 53 (25), pp.6482-6486. ⟨10.1002/anie.201402301⟩. ⟨hal-02023184⟩
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