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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting information Palladium nanoparticles supported on triazine functionalised mesoporous covalent organic polymers as efficient catalysts for Mizoroki-Heck cross coupling reaction Pillaiyar Puthiaraj a and Kasi Pitchumani a,b* a School of Chemistry, Madurai Kamaraj University, Madurai , India b Centre for Green Chemistry Processes, School of Chemistry, Madurai Kamaraj University, Madurai , India * pit2399@yahoo.com Contents. Characterization data S2 2. H, 3 C NMR spectral figures S0 S
2 . Characterization data 35 cps/ev S Pd C N O S Pd kev Fig. S. EDX of fresh Pd@MCOP Table S: Details of Atom weight percentage in fresh Pd@MCOP Element, Atomic number Series Atom (wt%) C, 6 K-series 64.4 N, 7 K-series 9.29 O, 8 K-series 3.96 Pd, 46 L-series 2.04 S, 6 K-series cps/ev S Pd C N O S Pd kev Fig. S. EDX of reused Pd@MCOP S2
3 Table S2: Details of Atom weight percentage in reused Element, Atomic number Series Atom (wt%) C, 6 K-series 69.4 N, 7 K-series 6.72 O, 8 K-series.52 Pd, 46 L-series 2.00 S, 6 K-series 0.62 NMR data for Mizoroki-Heck Cross Coupling products (E)-,2-diphenylethene (Table 3, Entry ): Compound 3a was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): 7.50 (d, J = 7.4 Hz, 4H), 7.35 (t, J = 7.5 Hz, 4H), 7.25 (t, 2H), 7.0 (s, 2H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 37.4, 28.8, 28.7, 27.6, H 3 CO (E)--methoxy-4-styrylbenzene (Table 3, Entry 2 and 22): Compound 3b was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): H NMR (400 MHz, CDCl3) δ (m, 4H), (t, 7.6 Hz, 2H), (m, H), (q, J = 38.0, 6.3 Hz, 2H), (m, H), (m, H), 3.82 (s, 3H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 59.4, 37.7, 30.2, 28.7, 28.6, 27.7, 27.2, 26.7, 26.3, 4.2, (E)--methyl-4-styrylbenzene (Table 3, Entry 3 and 23): Compound 3c was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J = 7.5 Hz, 2H), (d, J=8.0 Hz, 2H), (t, J = 7.6 Hz, 2H), (t, J=7.3 Hz, H), (d, J = 7.9 Hz, 2H), 7.07 (d, 2H), 2.35 (s, 3H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 37.6, 37.5, 34.6, 29.4, 28.7, 27.7, 27.4, 26.5, 26.4, 2.3. S3
4 O 2 N (E)--nitro-4-styrylbenzene (Table 3, Entry 4): Compound 3d was prepared according to the general procedure and purified by column chromatography to give a yellow solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): δ (d, J = 8.7 Hz, 2H), (d, J = 8.8 Hz, 2H), (d, J = 7.3 Hz, 2H), (m, 3H), (d, H), (d, H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 46.8, 43.9, 36.2, 33.3, 28.9, 28.9, 27., 26.9, 26.3, O (E)--(4-styrylphenyl)ethanone (Table 3, Entry 5): Compound 3e was prepared according to the general procedure and purified by column chromatography to give a pale yellow solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): 7.94 (d, J = 8.4 Hz, 2H), 7.57 (d, J = 8.4 Hz, 2H), 7.53 (d, J = 7.3 Hz, 2H), 7.37 (t, J = 7.5 Hz, 2H), 7.29 (t, J = 7.3 Hz, H), 7.22 (d, J = 6.4 Hz, H), 7.2 (d, J = 6.3 Hz, H), 2.60 (s, 3H).; 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 97.46, 42.0, 36.70, 35.96, 3.46, 28.87, 28.80, 28.32, 27.45, 26.82, 26.50, NC (E)--cyano-4-styrylbenzene (Table 3, Entry 6): Compound 3f was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (q, 4H), (d, 2H), (t, 2H), (m, H), (d, J = 6.3 Hz, H), (d, J = 6.3 Hz, H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 4.9, 36.3, 32.5, 32.4, , 26.9, 26.9, 26.8, 9.0, 0.6. F (E)--fluoro-4-styrylbenzene (Table 3, Entry 7): Compound 3g was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (m, 4H), (t, 2H), (t, H), m, 4H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 63.3, 6.2, 37.2, 33.5, 33.5, 28.7, 28.5, 28.4, 28.0, 28.0, 27.7, 27.5, 26.5, S4
5 5.7, 5.5. Cl (E)--chloro-4-styrylbenzene (Table 3, Entry 8): Compound 3h was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, 2H), (d, 2H), (t, 2H), (d, 2H), (d, H), (d, 2H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 37.0, 35.9, 33.2, 29.3, 28.8, 28.7, 27.9, 27.7, 27.4, H 3 CO (E)--methoxy-3-styrylbenzene (Table 3, Entry 9): Compound 3i was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J = 7.5 Hz, 2H), (t, J = 7.5 Hz, 2H), (m, 2H), (t, J = 3. Hz, 4H), (d, J = 8. Hz, H), 3.80 (s, 3H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 60.0, 38.9, 37.3, 29.7, 29., 28.8, 28.7, 27.8, 26.7, 9.4, 3.4,.9, H 3 CO H 3 CO (E)-,3-dimethoxy-5-styrylbenzene (Table 2, Entry 0): Compound 3j was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, 2H), (t, 2H), (t, H), (q, 2H), (d, 2H) 6.46 (s, H), 3.97 (s, 6H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm):6.04, 39.4, 37.2, 29.2, 28.7, 28.7, 27.9, 26.6, 04.6, 00.0, Cl Cl (E)-,3-dichloro-5-styrylbenzene (Table 3, Entry ): Compound 3k was prepared according to the general procedure and purified by column chromatography to give a white solid. S5
6 H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, 2H), (t, 2H), 7.38 (s, 2H), (t, H), 7.25 (s, H), (d, H), (d, H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 40.4, 36.3, 35.2, 32.3, 28.9, 28.5, 27.2, 26.8, 25.8, (E)--styrylnaphthalene (Table 3, Entry 2): Compound 3l was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J=7.9 Hz, H), (m, 2H), (d, J=8.2 Hz, H), (d, J=7. Hz, H), (d, J=7.8 Hz, 2H), (m, 3H), (t, J=7.6 Hz, 2H), (m, H), (d, J=6.2 Hz, H).; 3 C-NMR (00 MHz, 25 o C, CDCl3, δ ppm): 37.8, 35.2, 33.9, 3.9, 3.6, 28.9, 28.8, 28.2, 27.9, 26.9, 26.3, 26.0, 26.0, 25.9, 23.9, H 3 CO F (E)-2-fluoro--methoxy-4-styrylbenzene (Table 3, Entry 4): Compound 3m was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (500 MHz, CDCl 3, δ ppm): (d, 2H), (t, 2H), (t, 2H), (d, H), (m, 3H), 3.92 (s, 3H); 3 C-NMR (25 MHz, CDCl 3, δ ppm): 53.5, 5.6, 47.3, 47.2, 37.2, 3.0, 30.9, 28.7, 27.9, 27.6, 27.2,, 27.2, 26.4, 22.9, 22.9, 3.4, 3.3, 3.3, 3.3, O 2 N (E)--methyl-4-nitro-2-styrylbenzene (Table 3, Entry 3): Compound 3n was prepared according to the general procedure and purified by column chromatography to give a viscous yellow liquid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): 8.42 (s, H), 7.99 (dd, J = 8.3,.4 Hz, H), (d, 2H), (t, 2H), (m, 2H), (m, H), (d, J = 6. Hz, H), 2.50 (s, 3H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 46.7, 43., 37.7, 36.5, 32.8, 3., 28.8, 28.4, 26.8, 24.0, 2.8, 20., 20.. S6
7 NO 2 (E)--nitro-2-styrylbenzene (Table 3, Entry 5): Compound 3o was prepared according to the general procedure and purified by column chromatography to give a viscous yellow liquid. H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, H), (d, H), (m, 4H), (m, 3H), (d, H), (d, H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 48.0, 36.5, 33.9, 33.2,28.9, 28.7, 28.2, 28.0, 27., 24.8, 23.5.,3,5-tri((E)-styryl)benzene (Table 3, Entry 6): Compound 3p was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, 9H), (m, 6H), (m, 3H), (d, 3H), (d, 3H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 38., 37.3, 29.3, 28.8, 28.4, 27.8, 26.6, N (E)-3-styrylpyridine (Table 3, Entry 8): Compound 3q was prepared according to the general procedure and purified by column chromatography to give a brown solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): δ 8.72 (d, H), 8.48 (d, H), (d, J=7.9 Hz, H), (d, J=7.6 Hz, 2H), (t, J=7.5 Hz, 2H), (m, 3H), (d, J=6.4 Hz, H), (d, J=6.4 Hz, H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 48.6, 36.7, 33.0, 32.7, 30.9, 28.8, 28.2, 26.7, 24.9, S (E)-3-styrylthiophene (Table 2, Entry 9: Compound 3r was prepared according to the general procedure and purified by column chromatography to give a brown solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J = 7.4 Hz, 2H), S7
8 (m, 4H), (m, 2H), (d, J=6.3 Hz, H), (d, J=6.3 Hz, H).; 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 40.2, 37.4, 28.7, 27.5, 26.3, 26.2, 24.9, 22.9, S (E)-2-styrylthiophene (Table 3, Entry 20): Compound 3s was prepared according to the general procedure and purified by column chromatography to give a yellow solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J=7.4 Hz, 2H), (t, 2H), (m, 3H), (d, J = 3.5 Hz, H), (dd, J = 5., 3.6 Hz, H), (d, J = 6. Hz, H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 42.9, 37., 28.8, 28.4, 27.7, 26.4, 26.2, 24.4, 2.9. (E)-3-hexyl-2-styrylthiophene (Table 3, Entry 2): Compound 3t was prepared according to the general procedure and purified by column chromatography to give a viscous brown liquid. S H-NMR (500 MHz, 25 o C, CDCl 3, δ ppm): (d, 2H), (t, 2H) (m, H), (d, 2H), (d, H), (d, H), (t, 2H), (m, 2H), (m, 6H), (t, 3H); 3 C-NMR (25 MHz, 25 o C, CDCl 3, δ ppm): 4.2, 37.5, 36.3, 29.8, 28.7, 27.7, 27.4, 26.3, 23.0, 20.8, 3.8, 3.0, 29.2, 28.5, 22.7, 4.2. H 3 CO (E)--methoxy-4-(4-methylstyryl)benzene (Table 3, Entry 24): Compound 3u was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, J=8.7 Hz, 2H), (d, J=8. Hz, 2H), (d, J=8.0 Hz, 2H), (d, J=6.3 Hz, H), (d, H), (d, J=8.7 Hz, 2H), 3.80 (s, 3H), 2.34 (s, 3H); 3 C-NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 59.2, 37., 34.9, 30.4, 29.4, 27.6, 27.3, 26.6, 26.2, 4.2, 55.3, 2.3. S8
9 H 3 CO OCH 3 (E)-,2-bis(4-methoxyphenyl)ethene (Table 3, Entry 25): Compound 3v was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): (d, 4H), (m, 6H); 3 C- NMR (75 MHz, 25 o C, CDCl 3, δ ppm): 56.9, 28.4, 25.4, 24., 2., HOOC (E)-4-styrylbenzoic acid (Table 3, Entry 26): Compound 3w was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (400 MHz, 25 o C, CDCl 3, δ ppm): H NMR (400 MHz, DMSO) δ 2.9 (s, H), (d, 2H), (d, 2H), (d, 2H), (m, 5H); 3 C- NMR (00 MHz, 25 o C, CDCl 3, δ ppm): 67.0, 4.4, 36.6, 30.9, 29.7, 29.4, 28.7, 28.2, 27.4, 26.8, 26.4, 39.9, 39.7, 39.5, 39.3, 39.. N S (E)-4-methyl-5-(4-methylstyryl)thiazole (Table 3, Entry 27): Compound 3x was prepared according to the general procedure and purified by column chromatography to give a brown liquid. H-NMR (300 MHz, 25 o C, CDCl 3, δ ppm): 8.55 (s, H), (d, J = 8.0 Hz, 2H), (t, 2H), 7.09 (s, H), (d, J = 6.0 Hz, H), 2.53 (s, 3H), 2.36 (s, 3H); 3 C-NMR (75 MHz, 25 o C, CDCl 3, δ ppm): 50., 49., 37.9, 33.9, 3.4, 3., 29.4, 26.3, 7.2, 2.2, 5.3. COOCH 3 (E)-methyl cinnamate (Table 3, Entry and 28): Compound 3y was prepared according to the general procedure and purified by column chromatography to give a white solid. H-NMR (300 MHz, 25 o C, CDCl 3, δ ppm): (d, H), (m, 2H), (m, 3H), 3.8 (s, 3H); 3 C-NMR (75 MHz, 25 o C, CDCl 3, δ ppm): 67.3, 44.8, 34.3, 30.2, 28.9, 27.9, 7.7, 5.6. S9
10 Fig. S MHz H NMR spectrum of (E)-,2-diphenylethene (3a) Fig. S4. 00 MHz 3 C NMR spectrum of (E)-,2-diphenylethene (3a) S0
11 Fig. S MHz H NMR spectrum of (E)--methoxy-4-styrylbenzene (3b) Fig. S6. 00 MHz 3 C NMR spectrum of (E)--methoxy-4-styrylbenzene (3b) S
12 Fig. S MHz H NMR spectrum of (E)--methyl-4-styrylbenzene (3c) Fig. S8. 00 MHz 3 C NMR spectrum of (E)--methyl-4-styrylbenzene (3c) S2
13 Fig. S MHz H NMR spectrum of (E)--nitro-4-styrylbenzene (3d) Fig. S0. 00 MHz 3 C NMR spectrum of (E)--nitro-4-styrylbenzene (3d) S3
14 Fig. S. 400 MHz H NMR spectrum of (E)--(4-styrylphenyl)ethanone (3e) Fig. S2. 00 MHz 3 C NMR spectrum of (E)--(4-styrylphenyl)ethanone (3e) S4
15 Fig. S MHz H NMR spectrum of (E)--cyano-4-styrylbenzene (3f) Fig. S4. 00 MHz 3 C NMR spectrum of (E)--cyano-4-styrylbenzene (3f) S5
16 Fig. S MHz H NMR spectrum of (E)--fluoro-4-styrylbenzene (3g) Fig. S6. 25 MHz 3 C NMR spectrum of (E)--fluoro-4-styrylbenzene (3g) S6
17 Fig. S MHz H NMR spectrum of (E)--chloro-4-styrylbenzene (3h) Fig. S8. 25 MHz 3 C NMR spectrum of (E)--chloro-4-styrylbenzene (3h) S7
18 Fig. S MHz H NMR spectrum of (E)--methoxy-3-styrylbenzene (3i) Fig. S MHz 3 C NMR spectrum of (E)--methoxy-3-styrylbenzene (3i) S8
19 Fig. S MHz H NMR spectrum of (E)-,3-dimethoxy-5-styrylbenzene (3j) Fig. S MHz 3 C NMR spectrum of (E)-,3-dimethoxy-5-styrylbenzene (3j) S9
20 Fig. S MHz H NMR spectrum of (E)-,3-dichloro-5-styrylbenzene (3k) Fig. S MHz 3 C NMR spectrum of (E)-,3-dichloro-5-styrylbenzene (3k) S20
21 Fig. S MHz H NMR spectrum of (E)--styrylnaphthalene (3l) Fig. S MHz 3 C NMR spectrum of (E)--styrylnaphthalene (3l) S2
22 Fig. S MHz H NMR spectrum of (E)-2-fluoro--methoxy-4-styrylbenzene (3m) Fig. S MHz 3 C NMR spectrum of (E)-2-fluoro--methoxy-4-styrylbenzene (3m) S22
23 Fig. S MHz H NMR spectrum of (E)--methyl-4-nitro-2-styrylbenzene (3n) Fig. S MHz 3 C NMR spectrum of (E)--methyl-4-nitro-2-styrylbenzene (3n) S23
24 Fig. S MHz H NMR spectrum of (E)--nitro-2-styrylbenzene (3o) Fig. S MHz 3 C NMR spectrum of (E)--nitro-2-styrylbenzene (3o) S24
25 Fig. S MHz H NMR spectrum of,3,5-tri((e)-styryl)benzene (3p) Fig. S MHz 3 C NMR spectrum of,3,5-tri((e)-styryl)benzene (3p) S25
26 Fig. S MHz H NMR spectrum of (E)-3-styrylpyridine (3q) Fig. S MHz 3 C NMR spectrum of (E)-3-styrylpyridine (3q) S26
27 Fig. S MHz H NMR spectrum of (E)-3-styrylthiophene (3r) Fig. S MHz 3 C NMR spectrum of (E)-3-styrylthiophene (3r) S27
28 Fig. S MHz H NMR spectrum of (E)-2-styrylthiophene (3s) Fig. S MHz 3 C NMR spectrum of (E)-2-styrylthiophene (3s) S28
29 Fig. S MHz H NMR spectrum of (E)-3-hexyl-2-styrylthiophene (3t) Fig. S MHz 3 C NMR spectrum of (E)-3-hexyl-2-styrylthiophene (3t) S29
30 Fig. S MHz H NMR spectrum of (E)--methoxy-4-(4-methylstyryl)benzene (3u) Fig. S MHz 3 C NMR spectrum of (E)--methoxy-4-(4-methylstyryl)benzene (3u) S30
31 Fig. S MHz H NMR spectrum of (E)-4,4 -dimethoxystyrene (3v) Fig. S MHz 3 C NMR spectrum of (E)-4,4 -dimethoxystyrene (3v) S3
32 Fig. S MHz H NMR spectrum of (E)-4-styrylbenzoic acid (3w) Fig. S MHz 3 C NMR spectrum of (E)-4-styrylbenzoic acid (3w) S32
33 Fig. S MHz H NMR spectrum of (E)-4-methyl-5-(4-methylstyryl)thiazole (3x) Fig. S MHz 3 C NMR spectrum of (E)-4-methyl-5-(4-methylstyryl)thiazole (3x) S33
34 Fig. S MHz H NMR spectrum of methylacrylate (3y) Fig. S MHz 3 C NMR spectrum of methylacrylate (3y) S34
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