Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity

Youssra Doria Lahneche (1, 2) , Abdelhak Lachguar (1, 2) , Clément Mouton (2) , Jean-Claude Daran (2) , Eric Manoury (2) , Rinaldo Poli (2) , Meriem Benslimane (1) , Agnès Labande (2) , Éric Deydier (2)

1 CHEMS - Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale
2 LCC - Laboratoire de chimie de coordination

A new bidentate ferrocenyl phosphine/N-heterocyclic carbene (NHC) palladium complex rac-6, bearing a functionalized pendant arm for further grafting on a solid surface, has been synthesized in good yields and fully characterized. The molecular structure of proligand rac-4-BF4 and complex rac-6 were obtained by X-ray diffraction on single crystals. Kinetic studies demonstrated the good activity and stability of rac-6 in the Suzuki-Miyaura coupling of aryl bromides with arylboronic acids. The catalyst proved also to be active for the coupling of more challenging, bulky substrates such as 1-bromo-2-methylnaphthalene and naphthylboronic acid at relatively mild temperatures (40–70 °C) and low loadings (0.1–0.5 mol%). Experiments carried out with various amounts of water highlighted the role of water on both activity and mechanism.

Mots clés: Phosphine; N-heterocyclic carbene; Palladium; Suzuki-Miyaura; Kinetic study

Domaines: Chimie de coordination

Youssra Doria Lahneche, Abdelhak Lachguar, Clément Mouton, Jean-Claude Daran, Eric Manoury, et al.. Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity. Inorganica Chimica Acta, 2019, 492, pp.91-97. ⟨10.1016/j.ica.2019.04.021⟩. ⟨hal-02333616⟩