Magnetic apple seed starch functionalized with 2,2′‐furil as a green host for cobalt nanoparticles: Highly active and reusable catalyst for Mizoroki–Heck and the Suzuki–Miyaura reactions

Abstract

From the perspective of green chemistry, in catalytic systems, being low cost and eco‐friendly, in addition to high chemical and thermal stability, are requirements of support materials. In this regard, we used apple seed starch as an accessible, nontoxic, and cost‐effective support material. In order to take advantage of magnetic separation, the magnetite nanoparticles were chosen as an ideal pair for apple seed starch. Furthermore, during the Schiff base reaction, the magnetic apple seed starch was functionalized with 2,2′‐furil along with amine functionality to be used as a bio‐support for immobilization of cobalt. The introduction of cobalt had a significant effect on the greenness of the catalyst and reducing its price. FT‐IR, TGA, XRD, FE‐SEM, TEM, VSM, ninhydrin test, element mapping, AAS, and EDX analysis were applied to characterize the newly prepared catalyst. The effectiveness of this novel Schiff base supported catalyst was evaluated in the Mizoroki–Heck and the Suzuki–Miyaura coupling reactions. High reactivity and selectivity were among the most prominent characteristics of the catalyst as compared to previously reported catalysts. The longevity test and hot filtration showed the ability to use the catalyst at least 5 times and negligible cobalt leaching during the reaction, respectively. This work is the first report on the usage of apple seed starch as a supporting catalyst and 2,2′‐furil as a ligand in the catalyst modifications and catalytic activity. Accordingly, this can be the beginning of an attractive way in the design and synthesis of heterogeneous catalysts.

The untold story of starch as a catalyst for organic reactions

“…Arghan and colleagues reported a magnetic starch loaded with cobalt nanoparticles as a catalyst for the Mizoroki-Heck and the Suzuki-Miyaura reactions (Scheme 68). 196 To prepare the catalyst they coated the Fe 3 O 4 nanoparticles with starch and then modied the surface of starch with APTES. Using 2,2 0 -furil, they managed to achieve the related Schiff base.…”

“…Recently, Koukabi and Arghan used a little bit different magnetic catalyst compared to their previous work 196 to promote Mizoroki–Heck and Suzuki–Miyaura reactions. 198 They prepared the Fe 3 O 4 @starch core–shell like before, however, instead of modifying it with a linker they just added Co(OAc) 2 ·4H 2 O to the solution containing this magnetic structure to prepare their intended Fe 3 O 4 @starch-Co( ii ) catalyst.…”

Valorisation of Fruits, their Juices and Residues into Valuable (Nano)materials for Applications in Chemical Catalysis and Environment

“…Arghan and co-workers explored the synthesis of cobalt NPs immobilized on apple seed starch functionalized with 2,2'-furil that served as a magnetic nanocatalyst (Scheme 13). [94] This nanocatalyst can be used for Mizoroki-Heck and the Suzuki-Miyaura reactions (Scheme 14 and 15); highly stable catalyst presented good reactivity and selectivity in the reactions and decreased the energy and the time required for the Heck and Suzuki reactions (5 times recycled) in comparison to other reported Co-catalyzed cross-coupling reactions.…”