pH-Responsive chelating N-heterocyclic dicarbene palladium(ii) complexes: recoverable precatalysts for Suzuki–Miyaura reaction in pure water

Pd nanoparticles synthesized in situ with the use of Euphorbia granulate leaf extract: Catalytic properties of the resulting particles

“…In order to solve the problem, alternative environmentally benign processes for the Suzuki-Miyaura coupling reaction should be developed. There are some recent methods in the literature for Suzuki coupling reactions in water using soluble ligands and palladium homogeneous catalysts [13][14][15][16][17][18]. However, these methods suffer from certain disadvantages such as low TON (TON was only 20 when used up to 5.0 mol % of PdCl 2 ), high reaction temperature, long reaction times, tedious work-up, limited reusability of the expensive catalyst, which impacts cost, and palladium contamination in the product.…”

Palladium-Catalyzed Suzuki Reactions in Water with No Added Ligand: Effects of Reaction Scale, Temperature, pH of Aqueous Phase, and Substrate Structure

“…However, the limited solubility of the halogenated substrates and ligands in water often leads to slow rate and low yields. To overcome this limitation, alternative methodologies using water-soluble ligands, [52][53][54][55][56] organic co-solvents, [25][26][27][28][29][30][31][32] phase-transfer catalysts 33,[48][49][50][51] and inorganic salt promoters, 34,35 and heating with microwave or ultrasound were reported. [36][37][38][39][40] In 1989, Bumagin et al 57 were the first to report a Pd(OAc) 2 catalyzed Suzuki reaction of phenylboronic acid with aryl iodides containing a -OH or -COOH substituents; Na 2 CO 3 was employed as the base in neat water under an argon atmosphere.…”

An efficient Pd–NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

“…Since the pioneering report of a sulfonate-functionalized NHC ligand by Shaughnessy [40], a number of water-soluble NHC ligands, functionalized with sulfonate- [41–46], carboxylate- [47–52], polyether- [53–59] and other hydrophilic groups [60–63], have been developed and used in the aqueous Pd-catalyzed cross-coupling reactions. Among them, most of them were contributed to Suzuki–Miyaura reactions and only a very few examples were reported for Mizoroki–Heck reactions [45,51,53,57].…”