Supporting Information
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- Δελφίνια Δασκαλόπουλος
- 6 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information for Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium zinc base and regioselectivity-computed CH acidity relationship Mohamed Yacine Ameur Messaoud 1,2, Ghenia Bentabed-Ababsa* 2, Madani Hedidi 1,2, Aïcha Derdour 2, Floris Chevallier 1, Yury S. Halauko* 3, Oleg A. Ivashkevich 3, Vadim E. Matulis 4, Laurent Picot* 5, Valérie Thiéry* 5, Thierry Roisnel 6, Vincent Dorcet 6 and Florence Mongin* 1 Address: 1 Equipe Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10A, Case 1003, Campus de Beaulieu, Rennes, France, 2 Laboratoire de Synthèse Organique Appliquée, Faculté des Sciences, Université d Oran 1 Ahmed Ben Bella, BP 1524 El M Naouer, Oran, Algeria, 3 UNESCO Chair of Belarusian State University, 14 Leningradskaya Str., Minsk, , Belarus, 4 Research Institute for Physico-Chemical Problems of Belarusian State University, 14 Leningradskaya Str., Minsk, , Belarus, 5 Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, La Rochelle, France, and 6 Centre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1, Bâtiment 10B, Campus de Beaulieu, Rennes, France Ghenia Bentabed-Ababsa* - badri_sofi@yahoo.fr; Yury S. Halauko* - hys@tut.by; Laurent Picot* - laurent.picot@univ-lr.fr; Valérie Thiéry* - valerie.thiery@univ-lr.fr; Florence Mongin* - Florence.mongin@univ-rennes1.fr *Corresponding author Experimental description of the synthesized compounds, 1 H and 13 C NMR spectra, calculated values of the Gibbs energies G acid [kcal mo1 1 ] for deprotonation, selected Cartesian coordinates of molecular geometry for the most stable rotamer forms optimized at B3LYP/6-31G(d) level of theory S1
2 Table of Contents Experimental descriptions of the synthesized compounds... S3 1 H and 13 C NMR spectra of compounds 3a, 4a, 3b, 4d, 3e, 4e, 4c, 3d, 4d, 5b, 5d and 6d... S10 Calculated values of the Gibbs energies acid G [kcal mol -1 ] for deprotonation at the corresponding positions of the investigated compounds... S22 Cartesian coordinates of molecular geometries for most stable rotamer form of selected compounds (on example of 1b and 2b, neutral molecule, gas phase) optimized at B3LYP/6-31G(d) level of theory... S23 S2
3 N-(2-Thienyl)pyrrole (1a) [1]. The procedure 1 (16 h reaction time) using pyrrole (0.42 ml) and 2-iodothiophene (0.44 ml) (or 2-bromothiophene (0.39 ml)) gave 1a (eluent: heptane- CH 2 Cl 2 95:5) in 75% (20%) yield as a beige powder: mp 57 C; 1 H NMR (CDCl 3 ) 6.33 (t, 2H, J = 2.1 Hz), 6.91 (dd, 1H J = 3.6 and 1.5 Hz), (m, 1H), 6.99 (d, 1H, J = 1.5 Hz), 7.01 (t, 2H, J = 2.1 Hz); 13 C NMR (CDCl 3 ) (2CH), (CH), (2CH), (CH), (CH), (C). N-(3-Pyridyl)pyrrole (1b) [2]. The procedure 1 (32 h reaction time) using pyrrole (0.42 ml) and 3-iodopyridine (0.82 g) (or 3-bromopyridine (0.39 ml)) gave 1b (eluent: heptane-acoet 80:20) in 65% (26%) yield as a yellow oil: 1 H NMR (CDCl 3 ) 6.38 (t, 2H, J = 2.1 Hz), 7.07 (t, 2H, J = 2.3 Hz), 7.31 (dd, 1H J = 8.1 and 4.8 Hz), 7.64 (ddd, 1H, J = 8.4, 2.7 and 1.5 Hz), 8.47 (d, 1H, J = 4.5 Hz), 8.72 (d, 1H, J = 2.1 Hz); 13 C NMR (CDCl 3 ) (2CH), (2CH), (CH), (CH), (C), (CH), (CH). N-(4-Methoxyphenyl)pyrrole (1d) [3]. The procedure 1 (72 h reaction time) using pyrrole (0.42 ml) and 4-iodoanisole (0.94 g) gave 1d (eluent: heptane-ch 2 Cl 2 80:20) in 46% yield as a white powder: mp 110 C; 1 H NMR (CDCl 3 ) 3.84 (s, 3H), 6.33 (t, 2H, J = 2.1 Hz), (m, 2H), 7.01 (t, 2H, J = 2.1 Hz), (m, 2H); 13 C NMR (CDCl 3 ) 55.7 (CH 3 ), (2CH), (2CH), (2CH), (2CH), (C), (C). N-(4-Bromophenyl)pyrrole (1e) [4]. The procedure 1 (72 h reaction time) using pyrrole (0.42 ml) and 1-bromo-4-iodobenzene (1.1 g) gave 1e (eluent: heptane-ch 2 Cl 2 90:10) in 81% yield as a white powder: mp 92 C; 1 H NMR (CDCl 3 ) 6.41 (t, 2H, J = 2.3 Hz), 7.09 (t, 2H, J = 2.3 Hz), (m, 2H), (m, 2H); 13 C NMR (CDCl 3 ) (2CH), (C), (2CH), (2CH), (2CH), (C). N-(2-Thienyl)indole (2a) [5]. The procedure 1 (48 h reaction time) using indole (0.70 g) and 2-iodothiophene (0.44 ml) gave 2a (eluent: heptane-ch 2 Cl 2 90:10) in 50% yield as a yellow oil: 1 H NMR (CDCl 3 ) 6.92 (dd, 1H, J = 3.3 and 0.6 Hz), (m, 3H), (m, 3H), 7.87 (d, 1H, J = 8.1 Hz), 7.94 (dd, 1H J = 7.8 and 0.9 Hz); 13 C NMR (CDCl 3 ) (CH), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (C), (CH), (C), (C). N-(3-Pyridyl)indole (2b) [6]. The procedure 1 (48 h reaction time) using indole (0.70 g) and 3-iodopyridine (0.82 g) gave 2b (eluent: heptane-acoet 80:20) in 70% yield as a yellow oil: S3
4 1 H NMR (CDCl 3 ) 6.80 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 2H), 7.36 (d, 1H, J = 3.3 Hz), 7.48 (dd, 1H, J = 8.1 and 4.8 Hz), 7.59 (d, 1H, J = 8.1 Hz), (m, 1H), 7.85 (ddd, 1H, J = 8.1, 2.7 and 1.5 Hz), 8.65 (dd, 1H, J = 4.8 and 1.5 Hz), 8.89 (d, 1H J = 2.7 Hz); 13 C NMR (CDCl 3 ) (CH), (CH), (CH), (CH), (CH), (CH), (CH), (C), (CH), (C), (C), (CH), (CH). N-Phenylindole (2c) [7]. The procedure 1 (24 h reaction time) using indole (0.70 g) and iodobenzene (0.82 g) gave 2c (eluent: heptane-ch 2 Cl 2 90:10) in 30% yield as a yellow oil: 1 H NMR (CDCl 3 ) 6.73 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 2H), (m, 2H), (m, 4H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3 ) (CH), (CH), (CH), (CH), (CH), (2CH), (CH), (CH), (C), (2CH), (C), (C). N-(4-Methoxyphenyl)indole (2d) [8]. The procedure 1 (72 h reaction time) using indole (0.70 g) and 4-iodoanisole (0.94 g) gave 2d (eluent: heptane-ch 2 Cl 2 90:10) in 15% yield as a white powder: mp 58 C; 1 H NMR (CDCl 3 ) 3.89 (s, 3H), 6.68 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 2H), (m, 2H), 7.30 (d, 1H, J = 3.0 Hz), (m, 2H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3 ) 55.7 (CH 3 ), (CH), (CH), (2CH), (CH), (CH), (CH), (2CH), (CH), (C), (C), (C), (C). N-(4-Bromophenyl)indole (2e) [9]. The procedure 1 (56 h reaction time) using indole (0.70 g) and 1-bromo-4-iodobenzene (1.1 g) gave 2e (eluent: heptane-ch 2 Cl 2 90:10) in 60% yield as a yellow oil: 1 H NMR (CDCl 3 ) 6.74 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 2H), 7.32 (d, 1H, J = 3.3 Hz), (m, 2H), (m, 1H), (m, 2H), (m, 1H); 13 C NMR (CDCl 3 ) (CH), (CH), (C), (CH), (CH), (CH), (2CH), (CH), (C), (2CH), (C), (C). Crystal data for 2e. C 14 H 10 BrN, M = , monoclinic, P2 1 /n, a = (7), b = (12), c = (17) Å, β = (4), V = (3) Å 3, Z = 8, d = g cm -3, μ = mm -1. A final refinement on F 2 with 5231 unique intensities and 289 parameters converged at ωr(f 2 ) = (R(F) = ) for 3568 observed reflections with I > 2σ(I). N-(4-(Trifluoromethyl)phenyl)pyrrole (1f) [10]. The procedure 2 (24 h reaction time) using pyrrole (0.69 ml) and 1-iodo-4-(trifluoromethyl)benzene (1.8 ml) gave 1f (eluent: heptane- S4
5 AcOEt 90:10) in 96% yield as a white powder: mp 112 C; 1 H NMR (CDCl 3 ) 6.40 (t, 2H, J = 2.1 Hz), 7.14 (t, 2H, J = 2.1 Hz), 7.50 (d, 2H, J = 8.1 Hz), 7.69 (d, 2H, J = 8.4 Hz); 13 C NMR (CDCl 3 ) (2CH), (2CH), (2CH), (q, C, J = 270 Hz), (q, 2CH, J = 3.8 Hz), (q, C, J = 33 Hz), (C). N-(4-(Trifluoromethyl)phenyl)indole (2f) [11]. The procedure 2 (24 h reaction time) using indole (1.2 g) and 1-iodo-4-(trifluoromethyl)benzene (1.8 ml) gave 2f (eluent: heptane- CH 2 Cl 2 70:30) in 90% yield as a white powder: mp 62 C; 1 H NMR (CDCl 3 ) 6.76 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 2H), 7.38 (d, 1H, J = 3.3 Hz), (m, 3H), 7.73 (dm, 1H, J = 7.5 Hz), 7.81 (d, 1H, J = 8.4 Hz); 13 C NMR (CDCl 3 ) 10 (CH), (CH), (CH), (CH), (CH), (2CH), (q, C, J = 271 Hz), (q, 2CH, J = 3.7 Hz), (CH), (q, C, J = 32 Hz), (C), (C), (C). N-(5-iodo-2-thienyl)pyrrole (3a). The procedure 3 using N-(2-thienyl)pyrrole (1a, 0.15 g) gave 3a (eluent: heptane-acoet 80:20) in 97% yield as a beige powder: mp < 50 C; IR (ATR): 678, 722, 747, 769, 784, 810, 881, 937, 995, 1018, 1047, 1066, 1109, 1213, 1228, 1252, 1267, 1283, 1310, 1480, 1511, 1558, 1723, 2964 cm -1 ; 1 H NMR (CDCl 3 ) 6.37 (t, 2H, J = 2.1 Hz), 6.62 (d, 1H, J = 3.9 Hz), 6.97 (t, 2H, J = 2.1 Hz), 7.14 (d, 1H, J = 3.9 Hz); 13 C NMR (CDCl 3 ) 66.2 (C), (2CH), (CH), (2CH), (CH), (C); MS (ESI): calcd for C 8 H 6 INS [M] + 275, found 275. N-(5-Iodo-2-thienyl)indole (4a). The procedure 3 using N-(2-thienyl)indole (2a, 0.20 g) gave 4a (eluent: heptane-acoet 80:20) in 91% yield as a yellow oil; IR (ATR): 717, 739, 761, 793, 891, 944, 1014, 1131, 1196, 1213, 1226, 1285, 1306, 1331, 1457, 1475, 1516, 1550, 3051 cm - 1 ; 1 H NMR (CDCl 3 ) 6.79 (dd, 1H, J = 3.3 and 0.9 Hz), 6.83 (d, 1H, J = 3.9 Hz), (m, 4H), 7.70 (dm, 1H, J = 8.4 Hz), 7.80 (dm, 1H, J = 8.0 Hz); 13 C NMR (CDCl 3 ) 68.9 (C), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (C), (CH), (C), (C); MS (ESI): calcd for C 12 H 8 INS [M] + 325, found 325. N-(2-Iodo-3-pyridyl)pyrrole (3b). The procedure 4 using N-(3-pyridyl)pyrrole (1b, 72 mg) gave 3b (eluent: heptane-acoet 50:50) in 59% yield as a beige powder: mp C; IR (ATR): 705, 733, 815, 923, 1010, 1047, 1068, 1083, 1109, 1209, 1237, 1332, 1383, 1397, 1461, 1491, 1556, 3125 cm -1 ; 1 H NMR (CDCl 3 ) 6.34 (t, 2H, J = 2.2 Hz), 6.80 (t, 2H, J = 2.2 Hz), 7.33 (dd, 1H, J = 7.8 and 4.5 Hz), 7.50 (dd, 1H, J = 7.8 and 1.8 Hz), 8.37 (dd, 1H, J = S5
6 4.5 and 1.8 Hz); 13 C NMR (CDCl 3 ) (2CH), (C), (2CH), (CH), (CH), (C), (CH); MS (ESI): calcd for C 9 H 7 IN 2 [M] + 270, found 270. N-(2-Iodo-3-pyridyl)indole (4b). The procedure 4 using N-(3-pyridyl)indole (2b, 0.19 g) gave 4b (eluent: heptane-acoet 80:20) in 71% yield as a yellow oil; IR (ATR): 678, 709, 726, 744, 768, 811, 884, 1017, 1046, 1140, 1187, 1213, 1227, 1250, 1267, 1288, 1308, 1332, 1399, 1438, 1460, 1510, 1566, 2965, 3050 cm -1 ; 1 H NMR (CDCl 3 ) 6.75 (dd, 1H, J = 3.3 and 0.9 Hz), (m, 4H), 7.42 (dd, 1H, J = 7.8 and 4.5 Hz), 7.63 (dd, 1H, J = 7.8 and 1.8 Hz), (m, 1H), 8.49 (dd, 1H, J = 4.5 and 1.8 Hz); 13 C NMR (CDCl 3 ) (CH), (CH), (CH), (CH), (C), (CH), (CH), (CH), (C), (CH), (C), (C), (CH); MS (ESI): calcd for C 13 H 9 IN 2 [M] + 320, found Iodo-N-(3-iodo-4-methoxyphenyl)indole (4d ). The procedure 4 using N-(4- methoxyphenyl)-1h-indole (2d, 0.11 g) gave 4d (eluent: heptane-acoet 80:20) in 15% yield as a beige powder: mp 166 C; IR (ATR): 681, 731, 745, 782, 817, 906, 1018, 1046, 1147, 1212, 1248, 1265, 1286, 1309, 1440, 1464, 1490, 1564, 1595, 2838, 2939, 3061 cm -1 ; 1 H NMR (CDCl 3 ) 3.98 (s, 3H), 6.93 (d, 1H, J = 0.6 Hz), 6.95 (d, 1H, J = 8.7 Hz), (m, 3H), 7.32 (dd, 1H, J = 8.7 and 2.4 Hz), (m, 1H), 7.78 (d, 1H, J = 2.7 Hz); 13 C NMR (CDCl 3 ) 56.8 (CH 3 ), 84.5 (C), 85.6 (C), (CH), (CH), (CH), (CH), (CH), (CH), (C), (CH), (C), (C), (CH), (C); MS (ESI): calcd for C 15 H 11 I 2 NO [M] + 475, found 475. N-(4-Bromo-3-iodophenyl)pyrrole (3e). The procedure 4 using N-(4-bromophenyl)pyrrole (1e, 0.11 g) gave 3e (eluent: heptane-acoet 80:20) in 58% yield as a yellow powder: mp C; IR (ATR): 656, 723, 812, 867, 928, 1007, 1021, 1067, 1123, 1264, 1328, 1397, 1456, 1488, 1525, 1560, 1580, 2927, 3103 cm -1 ; 1 H NMR (CDCl 3 ) 6.38 (t, 2H, J = 2.2 Hz), 7.03 (t, 2H, J = 2.1 Hz), 7.23 (dd, 1H, J = 8.7 and 2.7 Hz), 7.62 (d, 1H, J = 8.7 Hz), 7.89 (d, 1H, J = 2.7 Hz); 13 C NMR (CDCl 3 ) (C), (2CH), (2CH), (CH), (C), (CH), (CH), (C). Crystal data for 3e. C 10 H 7 BrIN, M = , monoclinic, P2 1 /n, a = (5), b = (4), c = (10) Å, β = (3), V = (10) Å 3, Z = 4, d = g cm -3, μ = mm -1. A final refinement on F 2 with 2335 unique intensities and 118 parameters converged at ωr(f 2 ) = (R(F) = 0.032) for 1971 observed reflections with I > 2σ(I). S6
7 N-(4-Bromo-3-iodophenyl)indole (4e). The procedure 4 using N-(4-bromophenyl)indole (2e, 0.14 g) gave 4e (eluent: heptane-acoet 80:20) in 57% yield as a yellow oil: IR (ATR): 694, 738, 761, 820, 883, 907, 963, 1009, 1072, 1100, 1133, 1211, 1232, 1298, 1333, 1465, 1490, 1516, 1579, 1709, 1895, 2929, 3051 cm -1 ; 1 H NMR (CDCl 3 ) 6.70 (dd, 1H, J = 3.3 and 0.6 Hz), (m, 2H), 7.27 (d, 1H, J = 3.3 Hz), 7.38 (dd, 1H, J = 8.4 and 2.4 Hz), 7.52 (dd, 1H, J = 8.4 and 0.9 Hz), 7.68 (dd, 1H, J = 7.2 and 1.8 Hz), 7.74 (d, 1H, J = 8.7 Hz), 8.02 (d, 1H, J = 2.4 Hz); 13 C NMR (CDCl 3 ) (C), (CH), (CH), (CH), (CH), (CH), 12 (CH), (C), (CH), (C), (CH), (CH), (C), (C); MS (ESI): calcd for C 14 H 9 BrIN [M] + 397, found Iodo-N-phenylpyrrole (3c). The procedure 5 using commercial N-phenylpyrrole (1c, 95 mg) gave 3c (eluent: heptane-acoet 80:20) in 86% yield as a yellow oil; IR (ATR): 692, 710, 761, 782, 875, 940, 1033, 1072, 1116, 1299, 1320, 1388, 1431, 1457, 1496, 1513, 1597, 2925, 3047, 3103 cm -1 ; 1 H NMR (CDCl 3 ) 6.19 (dd, 1H, J = 3.6 and 3.0 Hz), 6.41 (dd, 1H, J = 3.6 and 1.8 Hz), 6.87 (dd, 1H, J = 3.0 and 1.8 Hz), (m, 5H); 13 C NMR (CDCl 3 ) 69.1 (C), (CH), (CH), (CH), (2CH), (CH), (2CH), (C). The analyses are similar to those previously reported [12]. 2-Iodo-N-phenylindole (4c). The procedure 5 using N-phenylindole (2c, 0.13 g) gave 4c (eluent: heptane-acoet 80:20), after recrystallization from pentane, in 92% yield as a yellow powder: mp 88 C; IR (ATR): 678, 691, 746, 763, 780, 809, 962, 1016, 1046, 1070, 1139, 1212, 1227, 1251, 1267, 1289, 1307, 1436, 1457, 1494, 1594, 2924, 3043 cm -1 ; 1 H NMR (CDCl 3 ) 6.99 (s, 1H), (m, 3H), (m, 2H), (m, 4H); 13 C NMR (CDCl 3 ) 83.9 (C), (CH), (CH), (CH), (CH), (CH), (CH), (2CH), (2CH), (C), (C), (C). Crystal data for 4c. C 14 H 10 IN, M = , monoclinic, C c, a = (3), b = (10), c = (5) Å, β = (2), V = (10) Å 3, Z = 4, d = g cm -3, μ = mm -1. A final refinement on F 2 with 2183 unique intensities and 145 parameters converged at ωr(f 2 ) = (R(F) = ) for 2139 observed reflections with I > 2σ(I). N-(3-Iodo-4-methoxyphenyl)pyrrole (3d). The procedure 6 using N-(4- methoxyphenyl)pyrrole (1d, 0.12 g) gave 3d (eluent: heptane-acoet 80:20) in 97% yield as a white powder: mp C; IR (ATR): 670, 739, 808, 885, 932, 1011, 1024, 1047, 1070, 1125, 1181, 1242, 1259, 1294, 1332, 1413, 1440, 1456, 1499, 1575, 1600, 2835, 2958, 3128 S7
8 cm -1 ; 1 H NMR (CDCl 3 ) 3.90 (s, 3H), 6.35 (t, 2H, J = 2.3 Hz), 6.85 (d, 1H, J = 8.7 Hz), 6.99 (t, 2H, J = 2.3 Hz), 7.34 (dd, 1H, J = 8.7 and 2.4 Hz), 7.83 (d, 1H, J = 2.7 Hz); 13 C NMR (CDCl 3 ) 56.7 (CH 3 ), 86.2 (C), (2CH), (CH), (2CH), (CH), (CH), (C), (C). Crystal data for 3d. C 11 H 10 INO, M = , monoclinic, P 2 1 /n, a = (4), b = (3), c = (8) Å, β = (2), V = (8) Å 3, Z = 4, d = g cm -3, μ = mm -1. A final refinement on F 2 with 2409 unique intensities and 128 parameters converged at ωr(f 2 ) = (R(F) = ) for 2149 observed reflections with I > 2σ(I). N-(3-Iodo-4-methoxyphenyl)indole (4d). The procedure 6 using N-(4-methoxyphenyl)indole (2d, 0.15 g) gave 4d (eluent: heptane-acoet 80:20), after recrystallization from pentane, in 71% yield as a beige powder: mp C; IR (ATR): 678, 726, 747, 768, 810, 885, 968, 1017, 1046, 1112, 1139, 1186, 1215, 1227, 1250, 1267, 1287, 1334, 1459, 1492, 1510, 1597, 2965 cm -1 ; 1 H NMR (CDCl 3 ) 3.96 (s, 3H), 6.68 (dd, 1H, J = 3.3 and 0.9 Hz), 6.94 (d, 1H, J = 8.7 Hz), (m, 2H), 7.26 (d, 1H, J = 2.7 Hz), (m, 2H), (m, 1H), 7.93 (d, 1H, J = 2.7 Hz); 13 C NMR (CDCl 3 ) 56.8 (CH 3 ), 86.2 (C), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (C), (C), (CH), (C), (C); MS (ESI): calcd for C 15 H 12 INO [M] + 349, found 349. N-(3-(1-Pyrrolyl)-2-pyridyl)imidazole (5b). The procedure 7 using N-(2-iodo-3- pyridyl)pyrrole (3b, 0.27 g) gave 5b (eluent: AcOEt-heptane 80:20) in 85% yield as a yellow oil: IR (ATR): 655, 728, 765, 810, 923, 972, 1013, 1048, 1072, 1093, 1213, 1239, 1260, 1302, 1335, 1446, 1493, 1582, 3119 cm -1 ; 1 H NMR (CDCl 3 ) 6.31 (t, 2H, J = 2.1 Hz), 6.61 (t, 2H, J = 2.1 Hz), 6.82 (s, 1H), 6.97 (s, 1H), 7.34 (dd, 1H, J = 7.8 and 4.8 Hz), 7.41 (s, 1H), 7.77 (dd, 1H, J = 8.1 and 1.7 Hz), 8.47 (dd, 1H, J = 4.8 and 1.7 Hz); 13 C NMR (CDCl 3 ) (2CH), (CH), (2CH), (CH), (C), (CH), (CH), (CH), (C), (CH); MS (ESI): calcd for C 12 H 10 N 4 [M] + 210, found 210. N-(2-Methoxy-5-(1-pyrrolyl)phenyl)imidazole (5d). The procedure 7 using N-(3-iodo-4- methoxyphenyl)pyrrole (3d, 0.30 g) gave 5d (eluent: AcOEt-heptane 80:20) in 67% yield as a beige powder: mp 130 C; IR (ATR): 659, 700, 723, 813, 985, 1019, 1032, 1055, 1070, 1247, 1263, 1281, 1464, 1496, 1520, 2841, 2937, 3109 cm -1 ; 1 H NMR (CDCl 3 ) 3.87 (s, 3H), 6.34 (t, 2H, J = 2.1 Hz), 7.01 (t, 2H, J = 2.1 Hz), 7.10 (d, 1H, J = 8.7 Hz), 7.19 (s, 1H), 7.23 (s, 1H), 7.32 (d, 1H, J = 2.7 Hz), 7.37 (dd, 1H, J = 8.7 and 2.7 Hz), 7.84 (s, 1H); 13 C NMR S8
9 (CDCl 3 ) 56.3 (CH 3 ), (2CH), (CH), (CH), (2CH), (CH), (CH), (C), (CH), (C), (CH), (C). Crystal data for 5d. C 14 H 13 N 3 O, M = , monoclinic, P 2 1 /n, a = (6), b = (3), c = (12) Å, β = (2), V = (12) Å 3, Z = 4, d = g cm -3, μ = mm -1. A final refinement on F 2 with 2777 unique intensities and 164 parameters converged at ωr(f 2 ) = (R(F) = ) for 2281 observed reflections with I > 2σ(I). N-(2-Methoxy-5-(1-indolyl)phenyl)imidazole (6d). The procedure 7 using N-(3-iodo-4- methoxyphenyl)indole (4d, 0.35 g) gave 6d (eluent: AcOEt-heptane 80:20) in 40% yield as a yellow oil: IR (ATR): 659, 704, 737, 762, 817, 884, 1022, 1055, 1093, 1106, 1134, 1212, 1226, 1251, 1286, 1457, 1491, 1519, 1591, 1609, 2841, 2932, 3051 cm -1 ; 1 H NMR (CDCl 3 ) 3.93 (s, 3H), 6.69 (d, 1H, J = 2.7 Hz), (m, 6H), (m, 3H), 7.69 (d, 1H, J = 7.2 Hz), 7.84 (br s, 1H); 13 C NMR (CDCl 3 ) 56.4 (CH 3 ), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (CH), (C), (CH), (C), (C), (C), (CH), (C); MS (ESI): calcd for C 18 H 15 N 3 O [M] + 289, found Reddy, V. P.; Kumar, A. V.; Rao, K. R. Tetrahedron Lett. 2011, 52, doi: /j.tetlet Teo, Y.-C.; Yong, F.-F.; Sim, S. Tetrahedron 2013, 69, doi: /j.tet Panda, N.; Jena, A. K.; Mohapatra, S.; Rout, S. R. Tetrahedron Lett. 2011, 52, doi: /j.tetlet Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, doi: /jo062060e 5 Tang, B.-X.; Guo, S.-M.; Zhang, M.-B.; Li, J.-H. Synthesis 2008, doi: /s Romero, M.; Harrak, Y.; Basset, J.; Ginet, L.; Constans, P.; Pujol, M. D. Tetrahedron 2006, 62, doi: /j.tet Kidwai, M.; Mishra, N. K.; Bhardwaj, S.; Jahan, A.; Kumar, A.; Mozumdar, S. ChemCatChem 2010, 2, doi: /cctc Rao, R. K.; Naidu, A. B.; Jaseer, E. A.; Sekar, G. Tetrahedron 2009, 65, doi: /j.tet Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur. J. 2006, 12, doi: /chem Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, doi: /jo Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Eur. J. Org. Chem. 2007, doi: /ejoc Seggio, A.; Lannou, M. I.; Chevallier, F.; Nobuto, D.; Uchiyama, M.; Golhen, S.; Roisnel, T.; Mongin, F. Chem. Eur. J. 2007, 13, doi: /chem S9
10 Compound 3a 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S10
11 Compound 4a 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S11
12 Compound 3b 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S12
13 Compound 4d 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S
14 Compound 3e 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S14
15 Compound 4e 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S15
16 Compound 4c 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S16
17 Compound 3d 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S17
18 Compound 4d 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S18
19 Compound 5b 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S
20 N N N Compound 5d MeO 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S20
21 Compound 6d 1 H NMR (300 MHz, CDCl 3 ) C NMR (75 MHz, CDCl 3 ) S21
22 S22
23 1b C C C C N H H C C C C H C H H H H H N S23
24 C C C C H H C C C C H C H H C C C C H H H H N H N b S24
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SUPPORTING INFORMATION FOR: Trialkylstibine complexes of boron, aluminium, gallium and indium trihalides: synthesis, properties and bonding Victoria K. Greenacre, William Levason and Gillian Reid Chemistry,
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