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Article Dans Une Revue Reaction Chemistry & Engineering Année : 2020

Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings

Résumé

Benzyloxycalix[8]arene is reported as a suitable macrocyclic support for Pd-NHC complexes, which catalyses CC crosscoupling reactions with high efficiency. Resulting PEPPSI-derived complexes, issued from a scalable synthetic procedure avoiding any tedious purification, are indeed used as heterogeneous catalysts in ethanol to promote the Suzuki-Miyaura coupling between various aryl halides and arylboronic acids (or esters). Optimisation of the reaction conditions allowed the use of only a slight excess of base (K3PO4, 1.2 equivalents) and boronic acid (1.1 equivalents), and these conditions were also successfully applied to a large scale benchmark reaction (1 mole of substrate) using a low palladium loading (0.001 mol %). Furthermore, target products were easily isolated after simple filtration procedures with low residual Pd traces (down to 3 ppm) thanks to the insoluble nature of the macrocyclic catalyst in ethanol, thus proving the usefulness of this support to promote coupling reactions relevant to the fine chemical industry.

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Chimie
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Dates et versions

hal-03052943 , version 1 (17-12-2020)

Identifiants

Citer

Axel Labattut, Sandra Abi Fayssal, Julien Buendia, Ibrahim Abdellah, Vincent Huc, et al.. Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings. Reaction Chemistry & Engineering, 2020, 5 (8), pp.1509-1514. ⟨10.1039/d0re00118j⟩. ⟨hal-03052943⟩
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