A highly efficient catalyst of a nitrogen-based ligand for the Suzuki coupling reaction at room temperature under air in neat water

Abstract

Glycine, as a kind of commercially available and inexpensive ligand, is used to prepare an air-stable and water-soluble catalyst for the Suzuki-Miyaura reaction in our study. In the presence of 0.1% [PdCl2(NH2CH2COOH)2] as the catalyst, extremely excellent catalytic activity towards the Suzuki-Miyaura coupling of aryl halides containing the carboxyl group with various aryl boronic acids is observed at room temperature under air in neat water.

C(sp2)−C(sp2) Coupling in Water: Palladium(II) Complexes of N‐Pincer Tetradentate Porphyrins as Effective Catalysts

“…Further,t he effect of base on SMC was studied at 85 8Ci n water by using various organic and inorganic bases (Table 3) and it wasf ound that two equivalents of the inorganic bases such as potassium carbonate, cesium carbonate, potassium phosphate tribasic, ands odium hydroxide display comparably high conversion (Table 3, entries 1-8) insteado fs odium acetate and potassium tert-butoxide (Table 3, entries 9a nd 10) and among these, K 2 CO 3 (2 equiv) showst he best results (Table 3, entry 3). No conversion was found with organic bases such as triethylamine, Hunig's base, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU;T able 3, entries [11][12][13].…”

“…[8] However, there are several efforts intended to develop modified, non-toxic, air-and moisture-resistant phosphine and non-phosphinel igands forS MC, [7] butt here is still ad emand to developn ew catalysts or ligands for SMC under mild and environmentally benign conditions. Recently,n itrogen ligands such as N,N'-dicyclohexyl 1,4-diazabutadiene (DAB-Cy), [9] oxine-5-sulfonic acid, [10] glycine, [11] O-aryloxime, [12] quinoline derivatives, [13] hydroquinidine 1,4-phthalazinediyl diether [(DHQD) 2 PHAL], [14] benzylhydrazone of thiophenea ldehyde, [15] and some other nitrogen-and sulfur-containing compounds [16] in the free-base form or as complexes with palladium were found to be attractive alternatives to phosphine ligands in palladium-catalyzed SMC, as thesea re exceptionally stable, readily availableo re asily synthesized,i nnocuous, and inert to moisture and air.S ince the first report on the use of Pd complexes of porphyrins as catalysts for Suzuki-Miyaura cross-coupling, [17] only af ew reports have appeared in the literatureo nt his topic. [18] However, the former [17] uses water as the reaction media but has limitations such as the significant loss of activity of catalyst when recycled and limited scope of substrates, and the latter three methods [18] use organic solvents as the reaction media/co-solvent.…”

Efficient synthesis of fluoro-containing liquid crystal materials via Pd-catalysed room temperature aerobic Suzuki reactions in aqueous media

“…[19,20] 2.2.2 General procedure for synthesis of target compounds (3a-f) Water (3 ml) and butanol (3 ml) were added into a dried round-bottom flask (50 ml) containing fluoro-containing phenylboronic acid (1.2 mmol), aryl halide (1 mmol), trans-PdCl 2 (NH 2 CH 2 COOH) 2 (0.01 mmol) and NaOH (3 mmol). The mixture was stirred at room temperature under aerobic conditions for 5 h. Then the resulting solution was extracted with ethyl acetate (10 ml × 3).…”

Functionalized Bis(triazolyl)phenylmethanol–palladium(II) Catalysts for Cross Coupling Reactions in Water

“…For modern synthetic chemistry, water has become a desirable solvent of choice due largely to its safety and availability compared to conventional organic solvents. A number of literatures have documented Pd catalyst systems supported by P(Ph) 2 ( m ‐C 6 H 4 SO 3 M) (M=Na + , K + ), N‐heterocyclic carbene (NHC)‐polymer, CNC‐pincer, ammonium‐functionalized pyridine–imidazole, and nitrogen‐based glycine ligands capable of promoting Suzuki–Miyaura reactions in neat water. Similarly, examples of copper‐free Pd catalysts for Sonogashira coupling in water have also been reported .…”