Supporting Information for jo051589t Synthesis of 2-Nitro and 2,2 -Dinitro-biphenyls by means of the Suzuki Cross-Coupling Reaction.
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1 upporting Information for jo051589t ynthesis of 2-Nitro and 2,2 -Dinitro-biphenyls by means of the uzuki Cross-Coupling Reaction. Raquel Rodríguez González, Lucia Liguori, Alberto Martinez Carrillo, and Hans-René Bjørsvik* Department of Chemistry, University of Bergen, Allégaten 41, N-5007 Bergen, Norway Table of content Experimental 1 General Methods 1 Compound data 1 1 H NMR spectrum of 3a 2,2 -dinitrobiphenyl 4 13 C NMR spectrum of 3a 2,2 -dinitrobiphenyl 5 1 H NMR spectrum of 4a 2-nitrobiphenyl 6 13 C NMR spectrum of 4a 2-nitrobiphenyl 7 1 H NMR spectrum of 4b 2-amino-2'-nitro-biphenyl 8 13 C NMR spectrum of 4b 2-amino-2'-nitro-biphenyl 9 1 H NMR spectrum of 4c 2-methoxy-2'-nitro-biphenyl C NMR spectrum of 4c 2-methoxy-2'-nitro-biphenyl 11 1 H NMR spectrum of 4d 2-methyl-2'-nitro-biphenyl C NMR spectrum of 4d 2-methyl-2'-nitro-biphenyl 13 1 H NMR spectrum of 4f 2-chloro-2'-nitro-biphenyl C NMR spectrum of 4f 2-chloro-2'-nitro-biphenyl 15 1 H NMR spectrum of 4g 2,4-dinitro-biphenyl C NMR spectrum of 4g 2,4-dinitro-biphenyl 17 1 H NMR spectrum of 10 3,3 -dinitrobiphenyl C NMR spectrum of 10 3,3 -dinitrobiphenyl 19 1 H NMR spectrum of 12 2,3'-Dinitrobiphenyl C NMR spectrum of 12 2,3'-Dinitrobiphenyl 21 1 H NMR spectrum of 13 3-Nitrobiphenyl C NMR spectrum of 13 3-Nitrobiphenyl 23 1 H NMR spectrum of 14 4-Nitrobiphenyl C NMR spectrum of 14 4-Nitrobiphenyl 25 Experimental General Methods. GLC analyses were performed on a capillary gas chromatograph equipped with fused silica column (L 25 m, 0.20 mm i.d., 0.33 µm film thickness) at a helium pressure of 200 kpa, split less /split injector and flame ionization detector. Mass spectra were acquired on a GC-M instrument using a gas chromatograph equipped with fused silica column (L 30 m, 0.25 mm i.d., 0.25µm film thickness) and He as carrier gas. 1 H-NMR spectra were recorded on NMR spectrometers operating at 200 MHz and 400 MHz. Chemical shifts were referenced to internal TM. tarting materials and reagents were purchased commercially and used without further purification. All of the reaction products are previously reported in the literature. The reaction products were analyzed by GC and GC-M and by comparison with authentic samples. ilica gel 60 ( mm) was used for the flash chromatography. F-254 TLC plates were used in order to follow the progress of the reactions, the purity of substance and to identify the various fractions from the flash chromatography separation. The spots of substances on the thin-layer were visualized under UV light. Compound data. O 2 N 2,2 -Dinitrobiphenyl [ ] C 12 H 8 N 2 O 4 MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 2H], [td, 2H], [td, 2H], [dd, 2H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 147.5, 134.5, 133.7, 131.3, 129.5, M (m/e) 198 (100), 182 (2), 168 (34), 152 (4), 139 (48), 127 (7), 115 (33), 102 (5), 89 (11), 75 (10), 63 (16). O 2 N 3,3 -Dinitrobiphenyl [ ] C 12 H 8 N 2 O 4 MW H NMR (200 MHz, DMO-d 6 -CD 3, ppm): δ [t, 2H], [dq, 2H], [dq, 2H], [t, 2H]. 13 C NMR (200 MHz, DMOd 6 -CD 3, ppm): δ 150.4, 141.7, 135.1, 132.0, 124.7, M (m/e) 244 (100), 198 (16), 186 (7), 168 (2), 152 (52), 139 (15), 126 (8), 102 (3), 87 (3), 76 (10), 63 (10). O 2 N 4,4 -Dinitrobiphenyl [ ] C 12 H 8 N 2 O 4 MW M (m/e) 244 (100), 214 (16), 198 (3), 181 (6), 168 (3), 152 (55), 139 (22), 126 (11), 114 (3), 102 (5), 87 (4), 75 (11), 63 (11). 1
2 O 2 N O 2 N 2,3 -Dinitrobiphenyl [ ] C 12 H 8 N 2 O 4 MW H NMR (200 MHz, CD 3, ppm): δ [t, 2H], [d, 1H], [dd, 1H], [m, 2H], [t, 2H]. 13 C NMR (200 MHz, CD 3, ppm): δ 149.6, 149.5, 140.8, 135.5, 134.5, 133.2, 133.0, 130.9, 130.7, 125.7, 123.9, M (m/e) 244 (70), 227 (10), 214 (4), 197 (15), 186 (18), 168 (64), 152 (78), 139 (100), 126 (36), 115 (48), 102 (19), 89 (16), 77 (31), 63 (45). O 2 N CH 3 4-Methyl-2,2 -Dinitrobiphenyl [ ] C 13 H 10 N 2 O 4 MW M (m/e) 212 (100), 196 (3), 181 (42), 167 (6), 152 (21), 141 (9), 128 (15), 115 (10), 89 (7), 77 (12), 63 (12). H 3 C O 2 N CH 3 4,4 -Methyl-2,2 -Dinitrobiphenyl [ ] C 14 H 12 N 2 O 4 MW M (m/e) 226 (100), 210 (10), 196 (37), 181 (10), 165 (10), 152 (15), 139 (4), 128 (7), 115 (7), 89 (4), 77 (9), 65 (6). H 3 CO 2-Methoxy-2 -nitrobiphenyl [ ] C 13 H 11 N 1 O 3 MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 1H], [td, 1H], [qd, 3H], [dd, 1H], [td, 1H], [d, 1H], 3.69 [s, 3H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 156.2, 142.2, 133.0, 132.8, 131.8, 130.1, 130.0, 128.3, 127.3, 124.2, 121.5, 110.9, M (m/e) 229 (100), 198 (17), 184 (10), 168 (53), 152 (17), 139 (55), 128 (17), 115 (27), 77 (12), 63 (13). H 3 CO 2,2 -Methoxybiphenyl [ ] C 14 H 14 O 2 MW M (m/e) 214 (100), 199 (12), 184 (22), 168 (18), 155 (7), 139 (13), 128 (15), 115 (10), 102 (5), 91 (5), 75 (3), 63 (7). OCH 3 H 2 N 2-Amino-2 -nitrobiphenyl [ ] C 12 H 10 N 2 O 2 MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 1H], [td, 1H], [qd, 2H], [t, 1H], [dd, 1H], [qd, 2H], 3.48 [s, 2H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 150.0, 144.0, 133.9, 133.2, 133.0, 129.8, 129.1, 129.0, 124.6, 123.6, 119.1, M (m/e) 214 (100), 197 (66), 180 (24), 167 (91), 152 (9), 139 (28), 128 (9), 115 (18), 83 (27), 77 (12), 63 (13). H 2 N 2,2 -Diaminobiphenyl [ ] C 12 H 12 N 2 MW M (m/e) 184 (100), 167 (54), 154 (4), 139 (7), 128 (6), 117 (3), 91 (13), 77 (9), 65 (6). NH 2 H 3 C 2-Methyl-2 -nitrobiphenyl 1 [ ] C 13 H 11 MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 1H], [dd, 1H], [m, 2H], [m, 4H], 1.99 [s, 3H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 149.4, 146.5, 137.5, 132.8, 132.4, 130.9, 130.3, 128.6, 128.5, 126.0, 125.5, 124.3, M (m/e) 213 (28), 196 (53), 183 (51), 165 (100), 152 (34), 139 (25), 128 (15), 115 (35), 82 (21), 76 (17), 63 (22). H 3 C 2,2 -Dimethylbiphenyl [ ] C 14 H 14 MW M (m/e) 182 (67), 167 (100), 152 (17), 139 (5), 128 (6), 115 (10), 89 (15), 82 (6), 76 (8), 63 (7). CH 3 CF 3 O 2 N 2-Nitro-2 -(trifluoromethyl)-biphenyl [ ] C 13 H 8 F 3 MW M (m/e) 267 (72), 217 (16), 201 (100), 168 (25), 151 (10), 139 (7), 115 (13), 100 (9), 75 (9), 63 (4). 2-Chloro-2 -nitrobiphenyl [ ] C 12 Cl MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 1H], [td, 1H], [dd, 1H], [td, 1H], [m, 4H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 148.9, 137.7, 134.6, 133.3, 132.7, 131.5, 130.2, 129.7, 129.7, 129.3, 127.3, M (m/e) 233 (1), 198 (100), 168 (20), 152 (29), 139 (12), 126 (6), 115 (15), 75 (11), 63 (7). Cl Cl Cl 2,2 -Dichlorobiphenyl [ ] C 12 H 8 Cl 2 MW M (m/e) 222 (98), 187 (42), 152 (100), 126 (6), 93 (12), 75 (22), 63 (6). 1 Iihama, T.; Fu, J.-m; Bourguignon, M.; nieckus, V. ynthesis 1989, 3,
3 O 2 N 2-Nitrobiphenyl 2, 3 [ ] C 12 H 9 MW H NMR (200 MHz, CDCl 3, ppm): δ [dd, 1H], [dd, 1H], [m, 5H], [m, 2H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 149.6, 137.7, 136.6, 132.6, 132.3, 129.0, 128.5, 128.5, 128.3, 128.2, M (m/e) 199 (31), 182 (44), 171 (47), 152 (100), 143 (33), 126 (20), 115 (81), 102 (9), 87 (8), 76 (35), 63 (21). 1,1 -Biphenyl [ ] C 12 H 12 MW M (m/e) 154 (100), 139 (2), 128 (5), 115 (3), 102 (2), 87 (2), 76 (16), 63 (5). H 2 N 2-Aminobiphenyl [ ] C 12 H 11 N MW M (m/e) 169 (100), 139 (8), 115 (10), 83 (14), 63 (6). O 2 N 2,4-Dinitrobiphenyl [ ] C 12 H 8 N 2 O 4 MW H NMR (200 MHz, CDCl 3, ppm): δ [d, 1H], [dd, 1H], [d, 1H], [m, 3H], [m, 2H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 147.2, 142.6, 135.9, 135.5, 133.5, 133.0, 129.9, 129.4, 128.3, 128.0, 126.8, M (m/e) 244 (13), 227 (19), 216 (46), 199 (7), 189 (6), 181 (7), 168 (30), 158 (19), 151 (85), 139 (100), 126 (40), 115 (54), 102 (33), 87 (18), 75 (30), 63 (33), 51 (21). 3-Nitrobiphenyl 4 [ ] C 12 H 9 MW H NMR (200 MHz, CDCl 3, ppm): δ 8.37 [s, 1H], [dd, 1H], [d, 1H], [d, 3H], [m, 3H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 148.8, 142.9, 138.7, 133.2, 129.9, 129.3, 128.7, 127.3, 122.1, M (m/e) 199 (100), 152 (79), 141 (7), 127 (7), 115 (5), 102 (3), 87 (2), 76 (13), 63 (6), 51 (5). 4 4-Nitrobiphenyl [ ] C 12 H 9 MW H NMR (200 MHz, CDCl 3, ppm): δ [d, 2H], [d, 2H], [dd, 2H], [m, 3H]. 13 C NMR (200 MHz, CDCl 3, ppm): δ 147.8, 147.3, 139.0, 129.4, 129.2, 128.0, 127.6, M (m/e) 199 (100), 169 (23), 152 (75), 141 (16), 127 (9), 115 (9), 102 (5), 87 (2), 76 (15), 63 (7), 51 (9). 2 Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. Tetrahedron. 2001, 57, D auria, M. Tetrahedon Lett. 1995, 36, Tao, B.; Boykin, D. W. J. Org. Chem. 2004, 69,
4 ppm (f1)
5 155.0 ppm (f1)
6 ppm (t1)
7 ppm (f1)
8 ppm (t1) NH 2 8
9 ppm (f1) NH
10 ppm (t1) OMe 10
11 ppm (f1) OMe
12 ppm (f1) CH
13 150 ppm (f1) CH
14 ppm (f1) Cl
15 ppm (f1) Cl
16 ppm (f1) O 2 N
17 ppm (f1) O2 N
18 ppm (t1) O2 N
19 160 ppm (t1) O 2 N
20 8.50 ppm (t1) O2 N O 2 N
21 155.0 ppm (t1) O 2 N O 2 N
22 ppm (f1)
23 ppm (f1)
24 ppm (f1)
25 ppm (f1)
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