Efficient cyanation of aryl halide with K₄[Fe(CN)₆]⋅3H₂O catalyzed by a P–O bidentate chelate palladium complex under air

Abstract

Cyanation of aryl halide with K 4 [Fe(CN) 6 ]Á3H 2 O has been carried out in the presence of a high-activity catalyst: an air-stable P-O bidentate chelate palladium complex. This method is applicable to both activated and deactivated aryl halides, and even a variety of aromatic nitriles are obtained in good yields under aerobic conditions.

Synthesis, Characterization, and Catalytic Study of Caffeine-Derived N-heterocyclic Carbene Palladium Complexes

“…17 Therefore, they were selected for a further substrate scope study (Table 3). Generally, the cyanation reaction preferred electron- deficient aryl bromides, affording the respective aryl nitriles in moderate yields (entries 1, 2, 4, and 6), while the reactivity toward deactivated species and 4-chloroacetophenone is not as efficient as those of a P−O bidentate chelate palladium complex 21 and a triazine-based covalent imine framework immobilized Pd(II) catalyst. 22…”

Fabrication of Pd Nanoparticles Embedded C@Fe3O4 Core–Shell Hybrid Nanospheres: An Efficient Catalyst for Cyanation in Aryl Halides

“…Our catalytic system is also compared (Supporting Information, Table S1) with reported Pd containing catalytic systems for cyanation of aryl halides. − The comparison table shows that most of the reported Pd catalysts are homogeneous in nature, use phosphine ligands, and possess high Pd content. However, the main disadvantage of using homogeneous catalysts is reusability.…”

“…The significant advantages of this reagent are (a) involvement of all the six CN – ions of K 4 [Fe­(CN) 6 ] in cyanation of aryl halides and this harnesses the full potential of the reagent and (b) the cyanide ion is strongly bound in potassium ferrocyanide­(II), warranting substantially slow release of cyanide ions which may be beneficial for reducing the inactivation of the catalyst. Since then a number of reports were available using this reagent in the presence of Pd catalysts such as Pd­(OAc) 2 , , several Pd complexes − and Pd/C , were developed. The serious drawbacks of these metal catalysts are metal contaminations in the final products, nonreusability, and deactivation of the catalysts associated with the use of the homogeneous system and hence are still unwelcoming.…”

Pd‐Polypyrrole Nanocomposite in Environmentally Friendly Synthesis of Vinylnitriles Using K4Fe(CN)6

“…Aryl iodides, bromides and chlorides turned to be active. The cyanation of inactivated aryl chlorides was of special importance since only a few examples of catalysts active for chlorides have been reported so far . This emphasizes the efficiency of the Pd/PPy composite under thermal activation.…”