K.O. Aghbash et al.
Molecular Catalysis xxx (xxxx) xxx
3 4 3 4 2
Fig. 2. FTIR spectra of Fe O @C, and Fe O @C-NHCS H.AuNPs.
2
.4. General synthesis of propargyl amines
NCH
HH =6.5 Hz, 2H of Ar), 7.51–7.53 (m, 1H of Ar), 7.76–7.77 (m, 1H of
Ar). 13C NMR (125 MHz, CDCl3): δ (ppm) 24.45 (NCH CH CH ), 26.14
(NCH CH CH ), 50.70 (NCH), 59.25 (NCH CH CH
), 85.81 (Ph-C≡C),
87.63 (HCN-C≡C), 123.17, 126.17, 128.13, 128.27, 128.76, 1-(1-(2-
chlorophenyl)-3-phenylprop-2-ynyl)morpholine: 1H NMR (CDCl , 500
MHz): δ (ppm) 2.69 (t, 3JHH =4.5 Hz, 4H, NCH CH O), 3.68–3.77 (m,
4H, NCH CH
2
CH
2
CH
2
), 5.12 (s, 1H of NCH), 7.25–7.29 (m, 2H of Ar), 7.34 (t,
3
J
First, 1 mmol of benzaldehyde, 1.2 mmol of morpholine, a 1.3 mmol
of phenylacetylene 0.4 g of Fe @C-NHCS H.AuNPs, and 1 mmol of
CO were added to 4 mL of CHCl and allowed to stirrer at room
c
2
2
2
3
O
4
2
2
2
2
2
2
2
K
2
3
3
temperature. The reaction progress was monitored by TLC method. After
completion of the reaction, the gold catalyst was removed by an external
magnet. The nanocatalyst was then washed with ethyl acetate (3 × 5
mL). The reaction solvent was evaporated to give paste for plate-
chromatography. The corresponding propargyl amines were analyzed
by physical properties, 1H NMR, and 13C NMR.
3
H
2
2
2
2
O), 4.95 (s, 1H of NCH), 7.29–7.36 (m, 5H of Ar),
7.42–7.44 (m, 1H of Ar), 7.51–7.53 (m, 2H of Ar), 7.76 (t, 3JHH =2.5 Hz,
1H of Ar).
1
-(1,3-diphenylprop-2-yn-1-yl)piperidine: 1H NMR (CDCl
MHz): δ (ppm) 1.46 (s, 3H, NCH CH CH ), 1.60–1.66 (m, 6H,
NCH CH CH ), 2.59 (s, 4H, NCH CH CH ), 4.83 (s, 1H of NCH),
.32–7.40 (m, 6H of Ar), 7.53–7.55 (m, 2H of Ar), 7.65 (d, 3JHH =7 Hz, 2
H).
3
, 500
3
. Results and discussion
H
2
2
2
2
2
2
2
2
2
In the present study, we designed DTC functionalized magnetic core-
7
shell for immobilization ultra-fine Au NPs. In this methodology, the
magnetic NPs coated via carbon for functionalized with DTC ligand to be
immobilized Au NPs and dispersible in the organic solvent. A schematic
4
-(1,3-diphenylprop-2-yn-1-yl)morpholine: 1H NMR (CDCl
MHz): δ (ppm) 2.66 (s, 2H, NCH CH O), 3.76 (t, 3JHH =5.5 Hz, 4H,
NCH CH
O), 4.82 (s, 1H of NCH), 7.33–7.41 (m, 6H of Ar), 7.53–7.55
m, 2H of Ar), 7.64 (d 3JHH =7.5 Hz, 2 H). 13C NMR (125 MHz, CDCl3):
(ppm) 62.03 (NCH), 67.17 (NCH CH
O), 85.03 (Ph-C≡C), 88.48
HCN-C≡C), 122.97, 127.78, 128.23, 128.31, 128.59, 131.81, 137.79.
-(3-phenyl-1-(p-tolyl)prop-2-yn-1-yl)morpholine: 1H NMR (CDCl
00 MHz): δ (ppm) 2.66 (s, 3H of Me), 2.71ꢀ 2.62 (m, 4H, NCH CH O),
.80ꢀ 3.71 (m, 4H, NCH CH O), 4.87 (s, 1H of NCH), 7.22ꢀ 7.19 (m, 2H
(ppm)
O), 85.3
Ph-C≡C), 88.5 (HCN-C≡C), 123.2, 128.3, 128.4, 128.6, 129.1, 131.7,
35.6, 137.6.
-(1-(2-chlorophenyl)-3-phenylprop-2-yn-1-yl)piperidine: 1H NMR
CDCl , 500 MHz): δ (ppm) 1.44 (t, 3JHH =5.5 Hz, 2H, NCH CH CH ),
.57–1.61 (m, 4H, NCH CH CH ), 2.63 (t, 3JHH =5.5 Hz, 4H,
3
, 500
H
2
2
illustration of the Fe
Scheme 2.
3 4 2
O @C-NHCS H.AuNPs synthesis is shown in
2
2
(
To verify this speculation, the morphology of the obtained nano-
sphere has been investigated through FESEM and TEM as shown in
δ
c
2
2
(
(
Fig. 1). The FESEM image (Fig. 1a) shown that the of the Fe
3 4
O @C-
4
3
,
NHCS H.AuNPs microspheres morphology. The surface of the micro-
2
5
3
H
2
2
sphere with DTC ligand helps for the stabilization of Au NPs and inhi-
bition from agglomeration. From the TEM images can provide more
detailed information that enables us to view the spherical Au NPs are
2
2
of Ar), 7.36ꢀ 7.33 (m, 3H of Ar). 13C NMR (125 MHz, CDCl3): δ
1.7 (CH ), 50.7 (NCH CH O), 61.7 (NCH), 67.9 (NCH CH
c
3
3
2
2
2
2
well-distributed on the surface of the Fe
3 4 2
O @C-NHCS H without sig-
(
nificant agglomeration. The size distribution histogram for Au NPs
1
(
Fig. 1d) shows a mean diameter of 3.3 ± 0.9 nm, which confirms that
1
Au NPs maintain its high monodispersity profile even after immobili-
zation on the support.
(
3
H
2
2
2
1
2
2
2
3 4
Fig. 2 exhibits the FT-IR spectra of Fe O @C and the individual Au
4