Amberlyst-15/[Bmim][PF 6 ] Catalyzed Synthesis of C 3 -Symmetric Triarylbenzenes via Cyclotrimerization of Alkynes
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1 Supporting Information Amberlyst-15/[Bmim][PF 6 ] Catalyzed Synthesis of C 3 -Symmetric Triarylbenzenes via Cyclotrimerization of Alkynes Kishor V. Wagh and Bhalchandra M. Bhanage Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai , India. Tel.: ; fax: ; bm.bhanage@gmail.com, bm.bhanage@ictmumbai.edu.in. Table of Contents: 1. General information s2 2. General experimental procedure S2 3. Characterization data of compounds s3-s6 4. Copies of 1 H NMR and 13 C NMR Spectra S7-S16 5. GC-MS chromatogram of crude model reaction mixture...s16 6. References...S17 S1
2 I. General information: All chemicals and reagents were acquired with their highest purity from various firms and were utilized as it is. GC with capillary column (Elite-1, 30 m 0.32 mm 0.25 µm) and flame ionization detector was used for analysis. GC-MS-QP 2010 instrument (Rtx-17, 30 m 25 mm ID, film thickness 0.25 µm df) (column flow 2 mlmin -1, 80 C to 240 C at 10 C/min rise). The triarylbenzenes were purified by column chromatography on mesh silica gel. The 1 H and 13 C NMR spectra were studied at 500 and 100 MHz in CD 3 solvent and TMS as an internal standard. Ionic liquids were prepared as per the procedure from literature. 64 II. Procedure for the synthesis of C 3 -symmetric triarylbenzenes via cyclotrimerization of alkynes: The Amberlyst-15 [H + exchange capacity (4.2 meq/g) and high surface area (42 m 2 /g)] (3 equiv.), [Bmim][PF 6 ] (2 ml) and 1a (3 mmol) was taken in reaction vessel. The reaction at 80 C for 12 h carried out and was monitored by GC/TLC. After the completion of reaction, 5 ml of di-isopropyl ether was used for extraction of product in the ether phase and the extraction procedure (2 5 ml) was repeated. The organic layers containing products were mixed and dried over anhydrous Na 2 SO 4. The crude product was purified on column chromatography [silica gel, mesh; PE:EA] and gave the corresponding product 2a in 88% yield. The 2a formation was confirmed by various spectroscopic techniques. The purity of product was studied by GC-MS analysis. Recyclability study: After extraction, the reaction vessel bearing the recovered Amberlyst-15/[Bmim][PF 6 ] was dried at 60 C in vacuo for an hour and then studied with 1a directly for next cycles. S2
3 3. Characterization data of compounds: (2a) 5'-phenyl-1,1':3',1''-terphenyl White solid: mp C (Ref. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.80 (s, 3H), (m, 6H), (t, 6H), (t, 3H). 13 C NMR (CD 3, 100 MHz) δ , , , , , ; FTIR (film): 3059, 3017, 1597, 1379, 1077, 856 cm - 1; GC-MS (EI) m/z (%) = 306 (100.0), 227 (4.48), 202 (3.82), 153 (4.3), 144 (5.6), 138 (3.6), 102 (1.2), 77(1.6). Anal. Calcd. for C 24 H 18 : C, 94.08; H, Found: C, 94.22; H, (2b) 4,4''-dimethyl-5'-(p-tolyl)-1,1':3',1''-terphenyl 2b White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.76 (s, 3H), (d, 6H), (d, 6H), 7.44 (s, 9H). 13 C NMR (CD 3, 100 MHz) δ , , , , , , 21.14; FTIR (film): 3027, 2930, 2861, 1512, 1449, 1109, 810 cm - 1; GC-MS (EI) m/z (%) = 348 (100.0), 333 (26.0), 318 (17.7), 255 (13.3), 239 (12.2), 151 (13.6), 111 (18.2), 97 (25.6). (2d) 4,4''-dimethoxy-5'-(4-methoxyphenyl)-1,1':3',1''-terphenyl White solid: mp C (lit. 1 mp 143 C); 1 H NMR (CD 3, 500 MHz) δ (d, 6H), 7.33 (s, 3H), (d, 6H), 2.47 (s, 9H). 13 C NMR (CD 3, 100 MHz) δ , , , , , , 55.35; FTIR (film): 3003, 2926, 1604, 1507, 1281, 1176, 1028, 825 cm - 1. Anal. Calcd. for C 27 H 24 O 3 : C, 81.79; H, Found: C, 81.99; H, S3
4 (2e) 4,4''-difluoro-5'-(4-fluorophenyl)-1,1':3',1''-terphenyl White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.67 (s, 3H), (d, 6H), (d, 6H). 13 C NMR (CD 3, 100 MHz) δ , , , (d, J= 7.5Hz), , (d, J= 22.5Hz); FTIR (film): 3045, 2926, 1607, 1505, 1138, 818 cm - 1; GC-MS (EI) m/z (%) = 360 (100.0) [M]+, 361 (M+1, 27.1), 338 (4.1), 318 (2.3), 264 (55.0), 244 (34.8), 180 (6.6), 159 (4.8), 75 (0.8). Anal. Calcd. for C 24 H 15 F 3 : C, 79.99; H, Found: C, 79.84; H, (2f) 4,4''-dichloro-5'-(4-chlorophenyl)-1,1':3',1''-terphenyl 2f White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.70 (s, 3H), (d, 6H), (d, 6H), (t, 3H). 13 C NMR (CD 3, 100 MHz) δ , , , , , ; FTIR (film): 3038, 2923, 1600, 1495, 1091, 1007, 812 cm - 1; Anal. Calcd. for C 24 H 15 3 : C, 70.35; H, Found: C, 70.09; H, (2g) 3,3''-dichloro-5'-(3-chlorophenyl)-1,1':3',1''-terphenyl 2g White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.72 (s, 3H), 7.66 (s, 3H), (d, 3H), (m, 6H). 13 C NMR (CD 3, 100 MHz) δ , , , , , , ; FTIR (film): 3059, 2926, 1597, 1383, 1081, 863 cm - 1. Anal. Calcd. for C 24 H 15 3 : C, 70.35; H, Found: C, 70.63; H, S4
5 (2h) 2,2''-dichloro-5'-(2-chlorophenyl)-1,1':3',1''-terphenyl 2h White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.60 (s, 3H), (m, 6H), (m, 6H), 13 C NMR (CD 3, 100 MHz) δ , , , , , , , ; Anal. Calcd. for C 24 H 15 3 : C, 70.35; H, Found: C, 70.51; H, (2i) 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl 2i White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 7.69 (s, 3H), (d, 6H), (d, 6H), 13 C NMR (CD 3, 100 MHz) δ , , , , , ; FTIR (film): 3056, 2930, 1612, 1593, 1484, 1078, 1007, 807 cm - 1. Anal. Calcd. for C 24 H 15 3 : C, 53.08; H, Found: C, 52.94; H, (2j) 4,4''-dichloro-5'-(4-chloro-3-methylphenyl)-3,3''-dimethyl-1,1':3',1''-terphenyl White solid: mp C; 1 H NMR (CD 3, 500 MHz) δ 7.68 (s, 3H), 7.53 (s, 3H), 7.44 (d, 3H), (d, 3H), 2.47 (s, 9H) 13 C NMR (CD 3, 100 MHz) δ , , , , , , , , , 20.25; FTIR (film): 3063, 2926, 1593, 1569, 1397, 1077, 856 cm - 1. Anal. Calcd. for C 27 H 21 3 : C, 71.77; H, Found: C, 71.80; H, S5
6 (2k) 1,3,5-tri(naphthalen-2-yl)benzene White solid: mp C (lit. 1 mp C); 1 H NMR (CD 3, 500 MHz) δ 8.91 (s, 3H), 8.24 (s, 3H), (m, 12H), (m, 6H); FTIR (film): 3024, 3000, 2954, 2835, 1607, 1512, 1291, 1235, 1035, 828 cm - 1. S6
7 4. Copies of 1 H NMR and 13 C NMR Spectra: (2a) 5'-phenyl-1,1':3',1''-terphenyl 1 H NMR (2a) 5'-phenyl-1,1':3',1''-terphenyl 13 C NMR S7
8 (2b) 4,4''-dimethyl-5'-(p-tolyl)-1,1':3',1''-terphenyl 1 H NMR 2b (2b) 4,4''-dimethyl-5'-(p-tolyl)-1,1':3',1''-terphenyl 13 C NMR 2b S8
9 (2d) 4,4''-dimethoxy-5'-(4-methoxyphenyl)-1,1':3',1''-terphenyl 1 H NMR OMe MeO 2d OMe (2d) 4,4''-dimethoxy-5'-(4-methoxyphenyl)-1,1':3',1''-terphenyl 13 C NMR OMe MeO 2d OMe S9
10 (2e) 4,4''-difluoro-5'-(4-fluorophenyl)-1,1':3',1''-terphenyl 1 H NMR (2e) 4,4''-difluoro-5'-(4-fluorophenyl)-1,1':3',1''-terphenyl 13 C NMR F F 2e F S10
11 (2f) 4,4''-dichloro-5'-(4-chlorophenyl)-1,1':3',1''-terphenyl 1 H NMR 2f (2f) 4,4''-dichloro-5'-(4-chlorophenyl)-1,1':3',1''-terphenyl 13 C NMR 2f S11
12 (2g) 3,3''-dichloro-5'-(3-chlorophenyl)-1,1':3',1''-terphenyl 1 H NMR 2g (2g) 3,3''-dichloro-5'-(3-chlorophenyl)-1,1':3',1''-terphenyl 13 C NMR S12
13 (2h) 2,2''-dichloro-5'-(2-chlorophenyl)-1,1':3',1''-terphenyl 1 H NMR 2h (2h) 2,2''-dichloro-5'-(2-chlorophenyl)-1,1':3',1''-terphenyl 13 C NMR 2h S13
14 (2i) 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl 1 H NMR 2i (2i) 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl 13 C NMR 2i S14
15 (2j) 4,4''-dichloro-5'-(4-chloro-3-methylphenyl)-3,3''-dimethyl-1,1':3',1''-terphenyl 1 H NMR (2j) 4,4''-dichloro-5'-(4-chloro-3-methylphenyl)-3,3''-dimethyl-1,1':3',1''-terphenyl 13 C NMR S15
16 (2k) 1,3,5-tri(naphthalen-2-yl)benzene 1 H-NMR 5. GC-MS chromatogram of crude reaction mixture of model reaction S16
17 6. References 1. Ono, F.; Ishikura, Y.; Tada, Y.; Endo, M.; Sato, T. Efficient conversion of acetophenones into 1,3,5-Triarylbenzenes catalyzed by bismuth(iii) trifluoromethanesulfonate tetrahydrate. Synlett 2008, 15, S17
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