Hybrid Organic‐Inorganic Materials from Di‐(2‐pyridyl)methylamine‐Palladium Dichloride Complex as Recoverable Catalysts for Suzuki, Heck and Sonogashira Reactions

Abstract

International audienceHybrid silica materials containing the di-(2-pyridyl)methylamine-palladium dichloride complex, prepared by sol-gel cogelification, are efficient recyclable catalysts for Suzuki (aryl bromides and chlorides), Heck (aryl bromides) and Sonogashira reactions (aryl iodides and bromides). Formation of palladium(0) nanoparticles is observed in the Suzuki and Heck reactions but not in the Sonogashira coupling

Suzuki–Miyaura Cross‐Coupling Reactions in Aqueous Media: Green and Sustainable Syntheses of Biaryls

“…This material was very active in the coupling of 4-bromoacetophenone with phenylboronic acid, even after 10 consecutive cycles. [110,111] They were also active for the coupling of 3-chlorobenzonitrile with phenylboronic acid. However, a study on a more diverse array of substrates would be necessary to determine the scope of these catalysts.…”

Silica-supported palladium: Sustainable catalysts for cross-coupling reactions

“…The resulting urea derivative was treated with PdCl 2 (CH 3 CN) 2 in anhydrous toluene at 90 • C overnight to afford the Pd(II) complex 1. Co-gelification of the silylated monomer 1 with different amounts of TEOS (1:10, 1:20, 1:40) was performed in dimethylformamide under standard sol-gel conditions with a stoichiometric amount of water and ammonium fluoride as catalyst, leading to Pd-containing materials 2a-c (Scheme 17) [44,45].…”

Robust and Electron‐Rich cis‐Palladium(II) Complexes with Phosphine and Carbene Ligands as Catalytic Precursors in Suzuki Coupling Reactions

“…[30] Notably, the dangling N-amido functionality on the ligand shows tolerance under the catalytic conditions, which allows future immobilization of catalyst on solid supports. [54][55][56] To probe the possible catalytic species responsible for the activity, we performed catalytic runs in which two equivalents of PR 3 (with respect to the catalyst) were added initially (Table 4). In comparison with the control run (entry 1), excess PR 3 slowed down the catalytic reactions prominently (entries 2 and 3), which reflects the involvement of phosphine dissociation for the formation of an active homogeneous (NHC)-Pd 0 species.…”