Fig 1.
General of A3-coupling reaction with Fe3O4@SiO2/CLM/Co/Mn magnetic nanocatalyst.
Fig 2.
Steps the synthesis of Fe3O4@SiO2/CLM/Co/Mn magnetic nanocatalyst.
2-i) Fe3O4, 2-ii) Fe3O4@SiO2, 2-iii) Fe3O4@ SiO2/Cl, 2-iv) Fe3O4@ SiO2/CL, 2-v) Fe3O4@ SiO2/CLOTs, 2-vi) Fe3O4@ SiO2/CLM and 2-vii) Fe3O4@ SiO2/CLM/Co/Mn.
Fig 3.
TEM, SEM and the Elemental Mapping analyses with a graphs that represents the order of nanoparticles.
a) Fe3O4, b) Fe3O4@SiO2, c) Fe3O4@SiO2/CLM and d) Fe3O4@SiO2/CLM/Co/Mn (TEM analysis), Fe, C, N, O, Si, Mn, Co (Elemental Scanning analysis), FE-SEM (left and right) and Diagrams 1, 2.
Fig 4.
FT-IR analysis Fe3O4@SiO2/CLM/Co/Mn.
4a) Fe3O4, 4b) Fe3O4@SiO2, 4c) Fe3O4@SiO2/Cl, 4d) Fe3O4@SiO2/CL and 4e) Fe3O4@SiO2/CLM/Co/Mn.
Fig 5.
EDX analysis of Fe3O4@SiO2/CLM/Co/Mn nanocatalyst.
Wt % measuring of Fe, O, Si, C, N, Co and Mn.
Fig 6.
XRD analysis to detect the structure of magnetic nanocatalyst.
6a) Fe3O4, 6b) Fe3O4@SiO2 and 6c) Fe3O4@SiO2/CLM/Co/Mn.
Fig 7.
UV analysis by the data`s adsorption of completed nanocatalyst.
7a) Fe3O4 and 7b) Fe3O4@SiO2/CLM/Co/Mn.
Fig 8.
VSM analysis of magnetic properties of magnetic nanocatalyst.
8a) Fe3O4, 8b) Fe3O4@SiO2 and 8c) Fe3O4@SiO2/CLM/Co/Mn.
Fig 9.
TGA analysis of nanocatalyst by steps.
9a) Fe3O4, 9b) Fe3O4@SiO2 and 9c) Fe3O4@SiO2/CLM/Co/Mn.
Fig 10.
BET and ICP-OES analyses of nanocatalyst before/after of multi cross-coupling reactions.
10a, 10c) BET analysis (The size of the holes = 6–8 nm) and 10b) ICP-OES analysis.
Fig 11.
TOF and TON formula for nanocatalysts [31].
11a) Table of TON/TOF measuring and 11b) Equation.
Table 1.
Data,s for A3-coupling reactions.
Fig 12.
A3-coupling reactions with optimism of reaction conditions in diagrams.
12a) general reaction of A3 coupling, 12b) Diagram 1 (products of A3 coupling) and 12c) Diagram 2 (optimum of solvents and times).
Fig 13.
TON/TOF measuring of multi cross-coupling products [37].
TON/TOFs values for evaluating A3-coupling reaction products.
Table 2.
Comparing of TON/TOF magnetic nanocatalyst in A3-coupling reactions.
Fig 14.
Standardized of A3-coupling products by melting point.
Times, yields % and TON/TOFs of products (L1-L12) which is the least yield for L3 and the most for L12 products.
Fig 15.
IR analysis of A3-coupling product.
This analysis is used for the detection of 1-(1,3-diphenylprop-2-yn-1-yl)pyrrolidine functional groups.
Table 3.
Comparing of Fe3O4@SiO2/CLM/Co/Mn nanocatalyst to other catalysts.
Fig 16.
Optical rotation of A3-coupling products with study on [31–39].
For L1-L6 products, the amount of optical rotation is evaluated as positive.
Fig 17.
Full reactions of A3-coupling.
The mechanism of 1-(1,3-diphenylprop-2-yn-1-yl)pyrrolidine product formation is generally shown in the presence of a base.
Fig 18.
Mechanism of A3-coupling reaction.
The multicomponent synthesis reaction was carried out in the presence of Fe3O4@SiO2/CLM/Co/Mn bimetallic magnetic nanocatalyst, and the proposed mechanism for it was presented.
Fig 19.
IR, SEM and TEM analyses with diagram of 10 periods of Fe3O4@SiO2/CLM/Co/Mn nanoparticles recycling reuse.
19a) Before multi-reaction reusing, 19b) After multi-reaction reusing, 19c) IR analysis of before multi-reaction reusing, 19d) IR analysis of after multi-reaction reusing and 19e) Reusing chart of Fe3O4@SiO2/CLM/Co/Mn magnetic nanocatalyst.
Fig 20.
Leaching analysis of nanocatalyst before and after reaction.
20a) Leaching measuring with nanocatlyst in full time that the slope of the graph was increasing and 20b) Leaching measuring without nanocatlyst in half the reaction completion time that the reaction was stopped.