Polystyrene-supported diaminocarbene complexes of palladium(II): synthesis, characterization and application as a precatalyst in Sonogashira–Hagihara and Suzuki–Miyaura cross coupling

Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity

“…For the catalytic studies, supported precatalysts 1 and 2 were prepared with a 30% modification of amino groups (1a and 2a), because such degree of modification is suitable for the reliable analysis of the solid phase (infrared spectroscopy (IR) and X-ray photoelectron spectroscopy (XPS)). The formation of the ADC-Pd II complexes on the surface of the resin was confirmed by the IR spectroscopy as the common method for this purpose in the case of polystyrene support [48].…”

“…In the latter case, special attention has been paid to the role of the support nature in the process of trapping the catalytically active particles after the reaction [47]. Unfortunately, describing the newly developed heterogeneous systems and their advantages, the authors do not always provide evidence of the true heterogeneous nature of catalysis [48].…”

Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes

“…To overcome these disadvantages, nowadays nucleophilic cyanation of aryl halides was performed using transition metals such as Pd [36][37][38][39][40][41][42][43][44][45][46][47][48][49][50], Ni [51] and Cu [52,53] under efficient conditions. Among the different solids for preparation of recyclable catalysts, organic polymers [54] having unique properties such as easy preparation steps, tunable hydrophilic-hydrophobic character and high loading of desired functional group are excellent materials for depositing metal nanoparticles [55]. Earlier, we reported about preparation heterogeneous palladium catalysts via immobilization of palladium(II) acyclic diaminocarbene (Pd(II)-ADC) complexes on resin support by metal-mediated addition of amino groups of benzhydrylamine-polystyrene to the coordinated isocyanide ligand of cis-PdCl 2 (CNR) 2 (R = t-Bu, Cy).…”

Synthesis and Crystal Structure of the Dirhodium Tetraacetate-Di(cyclohexylisocyanide) Complex

“…In organometallic chemistry, isocyanides are widely used as ligands. Coordination of isocyanides to electron-poor metal centres result in the electrophilic activation of the CN triple bond towards the addition of various nucleophiles [1][2][3][4][5][6]. The latter pathway serves as an attractive approach for the creation of complexes with both N-heterocyclic carbenes (M-NHCs) and acyclic diaminocarbenes (M-ADCs), which are unavailable via the classical transmetallation approach [1][2][3][4].…”

“…Following our interest in CN triple bond activation [1][2][3][4][5][6][7][8][9], here we report the synthesis of dirhodium tetraacetate di(cyclohexylisocyanide) [Rh 2 (O 2 CCH 3 ) 4 (C≡NCy) 2 ] (1) and the evaluation of the Rh(II) ability to activate isocyanides towards nucleophilic addition.…”