Supporting Information for
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- Κλυμένη Βιτάλης
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1 Supporting Information for Acceptorless Dehydrogenation of N-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-Indolyl-Pyridine Ligand Qingfu Wang,, Huining Chai,, and Zhengkun Yu*,, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian , People s Republic of China; University of Chinese Academy of Sciences, Beijing , People s Republic of China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai , People s Republic of China. zkyu@dicp.ac.cn Contents: 1. General considerations S2 2. X-Ray crystallographic studies S3 3. Analytical data S4 4. Copies of NMR spectra S16 S1
2 1. General considerations The spectroscopic features of known compounds 7a-7e, 1 7f, 2 7g, 3 7h, 1 7i-7j, 4 7k-7l, 1 7m, 5 7n, 6 7o, 3 7p-7q, 1 7r, 7 9a-9d, 1 9e, 8 9f-9j, 9 9k-9l, 10 9m, 11 9n, 12 11a-11b, 1 12a-12b, 1 14a, 13 14b, 14 14c, 15 14d-14j, 13 14k, 16 14l, 14 14m, 17 14n-14o, 18 14p, 17 14q, 19 and 14r 20 are in good agreement with those reported in the literatures. References (1) Wu, J.; Talwar, D.; Johnston, S.; Yan, M.; Xiao, J. Angew. Chem., Int. Ed. 2013, 52, (2) El-Damasy, A. K.; Seo, S. H.; Cho. N.-C.; Kang, S. B.; Pae, A. N.; Kim, K.-S.; Keum, G. J. Med. Chem. 2015, 101, (3) Mullick, K.; Biswas, S.; Angeles-Boza, A. M.; Suib, S. L. Chem. Commun. 2017, 53, (4) Kojima, M.; Kanai, M. Angew. Chem., Int. Ed. 2016, 55, (5) Brown, W. D.; Gouliaev, A. H. Synthesis 2002, 1, (6) Muthaiah, S.; Hong, S. H. Adv. Synth. Catal. 2012, 354, (7) Ucar, S.; Essiz, S.; Dastan, A. Tetrahedron 2017, 73, (8) Wang, X.-W.; Hua, Y.-Z.; Wang, M.-C. J. Org. Chem. 2016, 81, (9) He, K. H.; Tan, F. F.; Zhou, C. Z.; Zhou, G. J.; Yang, X. L.; Li, Y. Angew. Chem., Int. Chem. 2017, 56, (10) Zhang, J.; Chen, S.; Chen, F.; Xu, W.;Deng, G.-J.; Gong, H. Adv. Synth. Catal. 2012, 359, (11) Du, P.; Brosmer, J. L.; Peters, D. G. Org. Lett. 2011, 13, (12) Rodriguez-Dafonte, P.; Terrier, F.; Lakhdar, S.; Kurbatov, S.; Goumont, R. J. Org. Chem. 2009, 74, (13) Song, H.; Kang, B.; Hong, S. H. ACS Catal. 2014, 4, (14) Nelson, D. J.; Fernandez-Salas, J. A.; Truscott, B. J.; Nolan, S. P. Org. Biomol. Chem. 2014, 12, (15) Nobuta, T.; Hirashima, S.; Tada, N.; Miura, T.; Itoh, A. Org. Lett. 2011, 13, (16) Zhou, X.; Li, X.; Zhang, W.; Chen, J. Tetrahedron Lett. 2014, 55, (17) Baratta, W.; Bossi, G.; Putignano, E.; Rigo, P. Chem.-Eur. J. 2011, 17, S2
3 (18) Kawahara, R.; Fujita, K.; Yamaguchi, R. Angew. Chem., Int. Chem. 2012, 51, (19) Mo, F.; Lim, H. N.; Dong, G. J. Am. Chem. Soc. 2015, 137, (20) Li, X.; Wang, Y.; Gao, Y.; Li, L.; Guo, X.; Liu, D.; Jing, Y.; Zhao, L. Org. Biomol. Chem. 2014, 12, X-Ray crystallographic studies Figure S1. Molecular structure of 5b. Figure S1. Molecular structure of 5b. Table S1. Crystal data and structure refinement for 5b. Crystal system Monoclinic Space group P 21/c Unit cell dimensions a = (7) Å α= 90. b = (4) Å β= (3). c = (6) Å γ = 90. Volume (3) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 1952 Crystal size x x mm 3 Theta range for data collection to Index ranges Reflections collected <=h<=28, -13<=k<=12, -24<=l<=24 S3
4 Independent reflections 9565 [R(int) = ] Completeness to theta = % Absorption correction 3. Analytical data Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 9565 / 1 / 575 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient n/a Largest diff. peak and hole and e.å -3 Quinoline (7a): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 2 H), 7.73 (dd, J = 8.9, 4.8 Hz, 1 H), (m, 1 H), (m, 1H), 7.30 (td, J = 8.2, 4.5 Hz, 1H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 150.3, 148.2, 136.0, 129.4, 129.4, 128.2, 127.8, 126.5, Methylquinoline (7b): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.99 (d, J = 8.5 Hz, 1 H), 7.93 (d, J = 8.3 Hz, 1 H), 7.68 (d, J = 8.0 Hz, 1 H), (m, 1 H), 7.40 (dd, J = 7.8, 7.1 Hz, 1 H), 7.18 (d, J = 8.4 Hz, 1 H), 2.68 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 158.9, 147.8, 136.1, 129.4, 128.6, 127.5, 126.4, 125.6, 121.9, N Ph 2-Phenylquinoline (7c): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 3 H), 7.94 (d, J = 8.6 Hz, 1 H), (m, 3 H), (m, 4 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 157.3, 148.3, 139.7, 136.7, 129.7, 129.6, 129.3, 128.8, 127.6, 127.5, 127.2, 126.3, S4
5 3-Methylquinoline (7d): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 1 H), (m, 1 H), (m, 2 H), (m, 1 H), 2.30 (m, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 152.1, 146.2, 134.4, 130.2, 128.8, , 127.9, 126.9, 126.3, Methylquinoline (7e): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), 8.10 (d, J = 8.4 Hz, 1 H), 7.97 (dd, J = 7.1, 3.9 Hz, 1 H), 7.69 (td, J = 6.9, 1.6 Hz, 1 H), (m, 1 H), 7.20 (s, 1 H), 2.68 (d, J = 3.8 Hz, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 150.2, 148.1, 144.4, 130.1, 129.2, , 126.4, 123.9, 121.9, Methoxyquinoline (7f): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.84 (d, J = 2.4 Hz, 1 H), 8.49 (d, J = 8.3 Hz, 1 H), 7.67 (d, J = 8.6 Hz, 1 H), 7.53 (t, J = 8.1 Hz, 1 H), 7.28 (dd, J = 8.4, 4.2 Hz, 1 H), 6.74 (d, J = 7.6 Hz, 1 H), 3.88 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 155.0, 150.5, 148.9, 130.7, 129.3, 121.3, 120.7, 120.0, 104.1, Methoxyquinoline (7g): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.68 (m, 1 H), 7.94 (m, 2 H), (m, 2 H), 6.93 (m, 1 H), 3.80 (m, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ , 147.7, 144.2, 134.7, 130.6, 129.2, 122.2, 121.2, 105.0, Fluoro-2-methylquinoline (7h): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 1 H), (m, 1H), (m, 1 H), (m, 1 H), (m, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ (d, J = Hz), 158.5, 144.7, 135.2, (d, J = 9.0 Hz), (d, J = 13.4 Hz), 122.5, (d, J = 25.2 Hz), (d, J = 21.2 Hz), S5
6 8-Methylquinoline (7i): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 1 H), 7.61 (d, J = 7.5 Hz, 1 H), 7.54 (s, 1 H), (m, 2 H), 2.84 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 149.2, 147.3, 137.0, 136.3, 129.6, 128.2, 126.3, 125.9, 120.8, Benzo[h]quinoline (7j): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 9.35 (d, J = 8.1 Hz, 1 H), 9.01 (dd, J = 4.3, 1.5 Hz, 1 H), (m, 1 H), 7.90 (d, J = 7.8 Hz, 1H), (m, 2 H), (m, 1 H), 7.63 (d, J = 8.8 Hz, 1 H), 7.48 (dd, J = 7.9, 4.3 Hz, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 148.8, 146.6, 135.8, 133.7, , 128.2, 127.9, 127.8, 127.1, 126.4, 125.4, 124.4, Isoquinoline (7k): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 9.00 (s, 1 H), 8.30 (d, J = 5.8 Hz, 1 H), 7.60 (d, J = 8.2 Hz, 1 H), 7.46 (d, J = 8.2 Hz, 1 H), (m, 1 H), 7.30 (d, J = 5.8 Hz, 1 H), (m, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 152.0, 142.5, 135.2, 129.8, 128.1, 127.0, 126.7, 125.9, Phenylisoquinoline (7l): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.62 (d, J = 5.6 Hz, 1 H), 8.11 (d, J = 8.5 Hz, 1 H), 7.88 (d, J = 8.2 Hz, 1 H), (m, 4 H), (m, 4 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 160.8, 142.3, 139.6, 137.0, 130.1, 130.0, 128.7, 128.5, 127.7, 127.3, 127.1, 126.8, Bromoisoquinoline (7m): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 1 H), (m, 2 H), (m, 2 S6
7 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 151.8, 143.8, 137.1, 131.2, 130.6, 126.7, 126.4, 122.4, Isoquinoline (7n): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.72 (dd, J = 4.2, 1.6 Hz, 1 H), 8.21 (d, J = 8.2 Hz, 1 H), 7.92 (d, J = 9.2 Hz, 1 H), 7.43 (dd, J = 8.3, 4.2 Hz, 1 H), 7.38 (dd, J = 9.2, 2.8 Hz, 1 H), 7.31 (d, J = 2.8 Hz, 1 H), 3.86 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 157.3, 147.9, 143.9, 134.8, 130.4, 129.1, 122.1, 121.7, 105.7, Quinoxaline (7o): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.68 (s, 2 H), 7.95 (dd, J = 6.4, 3.5 Hz, 2 H), 7.59 (dd, J = 6.4, 3.4 Hz, 2 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 144.8, 142.8, 129.8, Methylquinoxaline (7p): yellow liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.65 (s, 1 H), 8.00 (d, J = 7.9 Hz, 1 H), 7.94 (d, J = 8.0 Hz, 1 H), 7.63 (dd, J = 9.0, 7.4 Hz, 2 H), 2.69 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 153.7, 145.9, 142.0, 140.9, 129.9, 129.1, 128.8, 128.6, Methylquinoxaline (7q): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.75 (m, 2 H), 7.86 (d, J = 7.1 Hz, 1 H), (m, 2 H), 2.71 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 144.5, 143.6, 143.1, 142.1, 137.6, 130.0, 129.7, 127.3, 77.5, 77.2, 76.8, Bromoquinoxaline (7r): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.79 (d, J = 1.8 Hz, 2 H), 8.23 (d, J = 2.0 Hz, 1 H), 7.91 (d, J = 8.9 Hz, 1 H), 7.78 (dd, J = 8.9, 2.0 Hz, 1 H), 7.26 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 145.7, 145.2, 143.5, 141.8, 133.7, 131.8, 130.9, S7
8 Indole (9a): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.98 (s, 1 H), 7.81 (d, J = 7.5 Hz, 1 H), 7.44 (d, J = 8.1 Hz, 1 H), (m, 1 H), (m, 1 H), (m, 1 H), (m, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 135.8, 127.9, 124.3, 122.0, 120.8, 119.9, 111.2, Methyl-1H-indole (9b): yellow solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.72 (s, 1 H), (m, 1 H), 7.28 (d, J = 7.5 Hz, 1 H), (m, 2 H), 6.27 (s, 1 H), 2.43 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 136.1, 135.2, 129.1, 121.0, 119.7, 110.4, 100.4, 77.5, 77.1, 76.8, Phenyl -1H-indole (9c): white solid. 1 H NMR (DMSO-d 6, 400 MHz, 23 C) δ (s, 1 H), 7.87 (d, J = 7.6 Hz, 2 H), 7.54 (d, J = 7.8 Hz, 1 H), 7.45 (dd, J = 14.3, 7.4 Hz, 3 H), 7.31 (t, J = 7.3 Hz, 1 H), 7.11 (t, J = 7.4 Hz, 1 H), 7.01 (t, J = 7.4 Hz, 1 H), 6.90 (d, J = 1.3 Hz, 1 H). 13 C{ 1 H} NMR (DMSO-d 6, 100 MHz, 23 C) δ 137.7, 137.2, 132.3, 129.0, 128.7, 127.4, 125.0, 121.6, 120.1, 119.4, 111.4, Methyl-1H-indole (9d): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.85 (s, 1 H), 7.67 (d, J = 7.8 Hz, 1 H), 7.40 (d, J = 8.0 Hz, 1 H), (m, 1 H), (m, 1 H), 7.01 (s, 1 H), 2.42 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 136.4, 128.4, 122.0, 121.7, 119.2, 118.9, 111.8, 111.1, Methoxy-1H-indole (9e): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.13 (s, 1 H), 7.30 (t, J = 7.8 Hz, 1 H), 7.09 (d, J = 8.5 Hz, 2 H), 6.85 (s, 1 H), 6.71 (d, J = 7.6 Hz, 1 H), 4.10 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 153.3, 137.2, 122.9, 122.7, 118.5, 104.7, 99.6, 99.6, S8
9 5-Methoxy-1H-indole (9f): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.11 (s, 1 H), 7.31 (d, J = 8.9 Hz, 1 H), (m, 2 H), 6.97 (dd, J = 8.8, 2.2 Hz, 1 H), 6.57 (s, 1 H), 3.95 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 154.2, 131.1, 128.3, 125.1, 112.4, 111.9, 102.4, 102.3, Methyl-1H-indole (9g): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.04 (s, 1 H), 7.55 (d, J = 7.7 Hz, 1 H), 7.21 (t, J = 2.8 Hz, 1 H), (m, 2 H), 6.60 (t, J = 2.3 Hz, 1 H), 2.52 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 135.5, 127.5, 123.9, 122.6, 120.3, 120.1, 118.6, 103.2, Fluoro-1H-indole (9h): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.08 (s, 1 H), 7.47 (d, J = 9.5 Hz, 1 H), 7.34 (dd, J = 8.4, 4.1 Hz, 1 H), 7.27 (s, 1 H), (m, 1 H), 6.66 (s, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ (d, J = Hz), 132.4, (d, J = 10.2 Hz), 126.2, (d, J = 9.7 Hz), (d, J = 26.2 Hz), (d, J = 23.2 Hz), (d, J = 4.7 Hz). 5-Chloro-1H-indole (9i): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.12 (s, 1 H), 7.71 (s, 1 H), 7.32 (d, J = 8.7 Hz, 1 H), 7.24 (d, J = 2.8 Hz, 2 H), 6.57 (s, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 134.2, 129.0, 125.7, 125.4, 122.3, 120.1, 112.2, Bromo-1H-indole (9j): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.08 (s, 1 H), 7.82 (s, 1 H), 7.32 and 7.23 (d each, J = 8.6 Hz, 1:1 H), 7.18 (s, 1 H), 6.53 (s, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 134.4, 129.7, 125.6, 124.8, 123.2, 113.0, 112.6, S9
10 5-Nitro-1H-indole (9k): yellow solid. 1 H NMR (CD 3 OD, 400 MHz, 23 C) δ 8.49 (s, 1 H), 7.98 (d, J = 8.7 Hz, 1 H), 7.42 (m, 2 H), 6.63 (s, 1 H). 13 C{ 1 H} NMR (CD 3 OD, 100 MHz, 23 C) δ 142.5, 140.6, 129.3, 128.6, 118.3, 117.6, 112.2, Chloro-1H-indole (9l): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.08 (s, 1 H), 7.57 (d, J = 8.4 Hz, 1 H), 7.37 (s, 1 H), 7.18 (t, J = 2.4 Hz, 1 H), 7.13 (d, J = 8.4 Hz, 1 H), 6.56 (s, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 136.2, 127.9, 126.5, 125.0, 121.7, 120.7, 111.1, ,6-Methylenedioxy-2-phenylindole (9m): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.24 (s, 1 H), 7.62 (d, J = 7.6 Hz, 2 H), 7.45 (t, J = 7.5 Hz, 2 H), 7.31 (d, J = 7.7 Hz, 1 H), 7.04 (s, 1 H), 6.90 (s, 1 H), 6.75 (s, 1 H), 5.98 (s, 2 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 145.3, 143.4, 132.6, 132.0, 129.1, 127.3, 124.7, 123.4, 100.8, 100.4, 99.3, Chloro-2-methyl-1H-indole (9n): yellow solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.81 (s, 1 H), 7.49 (s, 1 H), 7.16 (d, J = 8.5 Hz, 1 H), 7.07 (d, J = 8.5 Hz, 1 H), 6.17 (s, 1 H), 2.42 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 136.8, 134.5, 130.3, 125.3, 121.2, 119.1, 111.2, 100.3, Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (11a): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.14 (s, 1 H), 7.50 (d, J = 7.5 Hz, 1 H), 7.30 (d, J = 7.8 Hz, 1 H), 7.14 (dt, J = 14.7, 7.0 Hz, 2 H), 4.17 (q, J = 6.5 Hz, 1 H), 3.37 (dt, J = 12.8, 4.5 Hz, 1 H), (m, 1 H), (m, 2 H), 2.35 (d, J = 5.9 Hz, 1 H), S10
11 1.45 (d, J = 6.7 Hz, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 137.0, 135.8, 127.6, 121.6, 119.4, 118.2, 110.9, 108.4, 48.3, 42.7, 22.7, Phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (11b): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.01 (s, 1 H), 7.59 (dd, J = 5.6, 2.9 Hz, 1 H), 7.37 (dd, J = 6.5, 3.5 Hz, 3 H), (m, 2 H), (m, 3 H), 5.12 (s, 1 H), 3.34 (dt, J = 9.1, 4.8 Hz, 1 H), (m, 1 H), (m, 1 H), (m, 1 H), 1.97 (s, 1 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 141.8, 136.0, 134.5, 128.9, 128.6, 128.3, 127.4, 121.7, 119.4, 118.3, 110.9, 110.2, 58.1, 42.8, Methyl-9H-pyrido[3,4-b]indole (12a): white solid. 1 H NMR (DMSO-d 6, 400 MHz, 23 C) δ (s, 1 H), 8.18 (d, J = 6.8 Hz, 2 H), 7.91 (d, J = 3.3 Hz, 1 H), 7.60 (d, J = 7.6 Hz, 1 H), 7.52 (t, J = 7.1 Hz, 1 H), 7.22 (t, J = 6.7 Hz, 1 H), 2.76 (s, 3 H). 13 C{ 1 H} NMR (DMSO-d 6, 100 MHz, 23 C) δ 142.2, 140.4, 137.6, 134.6, 127.9, 127.0, 121.8, 121.1, 119.3, 112.7, 112.0, Phenyl-9H-pyrido[3,4-b]indole (12b): white solid. 1 H NMR (DMSO-d 6, 400 MHz, 23 C) δ (s, 1 H), 8.46 (d, J = 5.1 Hz, 1 H), 8.25 (d, J = 7.8 Hz, 1 H), 8.11 (d, J = 5.1 Hz, 1 H), 8.04 (d, J = 7.8 Hz, 2 H), 7.67 (d, J = 8.2 Hz, 1 H), 7.61 (t, J = 7.5 Hz, 2 H), 7.53 (dt, J = 14.5, 7.3 Hz, 2 H), 7.26 (t, J = 7.5 Hz, 1 H). 13 C{ 1 H} NMR (DMSO-d 6, 100 MHz, 23 C) δ 142.2, 141.2, 138.4, 133.1, 129.3, 128.8, 128.6, 128.4, 128.2, 121.6, 120.9, 119.6, 113.9, Acetophenone (14a): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.95 (d, J = 7.5 Hz, 2 H), 7.56 (t, J = 7.3 Hz, 1 H), 7.45 (t, J = 7.7 Hz, 2 H), 2.60 (s, 3 S11
12 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 198.2, 137.2, 133.2, 128.7, 128.4, Propiophenone (14b): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 2 H), (m, 1 H), 7.44 (dd, J = 10.5, 4.6 Hz, 2 H), 3.00 (q, J = 7.2 Hz, 2 H), 1.22 (t, J = 7.2 Hz, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 200.9, 137.0, 133.0, 128.6, 128.1, 31.9, '-Methylacetophenone (14c): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.72 (d, J = 7.6 Hz, 1 H), 7.40 (t, J = 7.5 Hz, 1 H), 7.28 (dd, J = 11.8, 7.6 Hz, 2 H), 2.60 (s, 3 H), 2.56 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 201.8, 138.5, 137.7, 132.1, 131.6, 129.4, 125.8, 29.6, '-Methylacetophenone (14d): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) 7.73 (m, 2 H), 7.31 (m, 2 H), 2.54 (s, 3 H), 2.37 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 198.1, 138.2, 137.0, 133.7, 128.6, 128.3, 125.4, 26.5, '-Methylacetophenone (14e): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.89 (d, J = 8.2 Hz, 2 H), 7.29 (d, J = 8.0 Hz, 2 H), 2.61 (s, 3 H), 2.44 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 198.1, 144.0, 134.9, 129.4, 128.6, 26.6, '-Methoxyacetophenone (14f): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.88 (d, J = 8.9 Hz, 2 H), 6.88 (d, J = 8.9 Hz, 2 H), 3.81 (s, 3 H), 2.50 (s, 3 S12
13 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 196.7, 163.5, 130.6, 130.3, 113.7, 55.4, '-Chloroacetophenone (14g): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 2 H), (m, 2 H), 2.58 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 196.9, 139.7, 135.6, 129.9, 129.0, '-Trifluoromethylacetophenone (14h): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.0 (d, J = 8.1 Hz, 2 H), 7.7 (d, J = 8.2 Hz, 2 H), 2.6 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 197.0, 139.8, (q, J = 32.5 Hz), 128.7, (q, J = 3.7 Hz), (q, J = Hz), Acetophenone (14i): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 8.44 (s, 1 H), 8.02 (d, J = 8.6 Hz, 1 H), 7.94 (d, J = 8.0 Hz, 1 H), 7.86 (dd, J = 8.3, 3.7 Hz, 2 H), 7.56 (dt, J = 14.9, 6.9 Hz, 2 H), 2.70 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 198.1, 135.6, 134.5, 132.6, 130.2, 129.6, 128.5, 128.4, 127.8, 126.8, 123.9, Benzophenone (14j): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 4 H), 7.59 (dd, J = 10.6, 4.2 Hz, 2 H), 7.48 (t, J = 7.6 Hz, 4 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 196.8, 137.7, 132.5, 130.2, ,5-Diphenylpentan-3-one (14k): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 10 H), 2.94 (t, J = 7.5 Hz, 4 H), 2.76 (t, J = 7.5 Hz, 4 H). S13
14 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 209.2, 141.1, 128.6, 128.4, 126.2, 44.6, Phenylbutan-2-one (14l): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 7.33 (t, J = 7.2 Hz, 2 H), 7.24 (t, J = 6.6 Hz, 3 H), 2.94 (t, J = 7.5 Hz, 2 H), 2.80 (t, J = 7.6 Hz, 2 H), 2.18 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 207.9, 141.0, 128.5, 128.3, 126.1, 45.2, 30.1, O 4 Heptan-2-one (14m): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 2.40 (t, J = 7.5 Hz, 2 H), 2.12 (s, 3 H), (m, 2 H), (m, 4 H), 0.88 (t, J = 7.0 Hz, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 209.5, 43.9, 31.5, 30.0, 23.7, 22.6, O 5 Octan-2-one (14n): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 2.41 (t, J = 7.5 Hz, 2 H), 2.12 (s, 3 H), (m, 2 H), 1.28 (m, 6 H), 0.87 (t, J = 6.7 Hz, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 209.6, 44.0, 31.7, 30.0, 29.0, 24.0, 22.6, Cyclohexanone (14o): colorless liquid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 2.31 (t, J = 6.7 Hz, 4 H), (m, 4 H), (m, 2 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 212.4, 42.0, 27.1, Cholest-4-en-3-one (14p): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ1h NMR (400 MHz, CDCl3) δ 5.72 (s, 1 H), (m, 4 H), (m, 2 H), 1.84 S14
15 (m, 2 H), (m, 4 H), 1.35 (m, 4 H), 1.15 (m, 12 H), 1.01 (m, 2 H), 0.93 (m, 10 H), 0.70 (m, 4 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) 199.8, 171.9, 123.9, 56.2, 56.0, 53.9, 42.5, 39.7, 39.6, 38.7, 36.2, 35.9, 35.8, 35.7, 34.1, 33.1, 32.2, 28.3, 28.1, 24.3, 23.9, 23.0, 22.7, 21.1, 18.8, 17.5, Dihydrocholesterone (14q): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ (m, 1 H), (m, 2 H), (m, 3 H), (m, 1 H), (m, 1 H), (s, 4 H), (m, 8 H), (m, 12 H), (dd, J = 6.5, 1.2 Hz, 10 H), (m, 1 H), 0.66 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 212.1, 56.4, 53.9, 46.8, 44.8, 42.7, 40.0, 39.6, 38.7, 38.3, 36.3, 35.9, 35.7, 35.5, 31.8, 29.1, 28.3, 28.1, 24.3, 23.9, 22.9, 22.7, 21.6, 18.8, 12.2, (18β,20β)-3,11-Dioxoolean-12-en-29-oic acid methyl ester (14r): white solid. 1 H NMR (CDCl 3, 400 MHz, 23 C) δ 5.68 (s, 1 H), 3.67 (s, 3 H), 2.95 (m, 1 H), 2.61 (m, 1 H), 2.42 (s, 1 H), 2.34 (m, 1 H), (m, 3 H), (m, 2 H), (m, 5 H), (m, 13 H), 1.15 (t, J = 7.3 Hz, 6 H), 1.07 (d, J = 14.3 Hz, 6 H), 0.80 (s, 3 H). 13 C{ 1 H} NMR (CDCl 3, 100 MHz, 23 C) δ 217.2, 199.5, 177.0, 169.8, 128.6, 61.2, 55.5, 51.9, 48.5, 47.9, 45.3, 44.1, 43.4, 41.3, 39.9, 37.9, 36.8, 34.3, 26.5, 23.4, 21.5, 18.9, S15
16 4. Copies of NMR spectra Figure S2. 1 H NMR spectrum of 3a (CDCl 3, 400 MHz, 23 o C). Figure S3. 13 C{ 1 H} NMR spectrum of 3a (CDCl 3, 100 MHz, 23 o C). S16
17 Figure S4. 1 H NMR spectrum of 3b (CDCl 3, 400 MHz, 23 o C). Figure S5. 13 C{ 1 H} NMR spectrum of 3b (CDCl 3, 100 MHz, 23 o C). S17
18 Figure S6. 1 H NMR spectrum of 3c (CDCl 3, 400 MHz, 23 o C). Figure S7. 13 C{ 1 H} NMR spectrum of 3c (CDCl 3, 100 MHz, 23 o C). S18
19 Figure S8. 1 H NMR spectrum of 4a (CDCl 3, 400 MHz, 23 o C). Figure S9. 13 C{ 1 H} NMR spectrum of 4a (CDCl 3, 100 MHz, 23 o C). S19
20 Figure S P NMR spectrum of complex 4a (CDCl 3, 162 MHz, 23 o C). Figure S11. 1 H NMR spectrum of 4b (CDCl 3, 400 MHz, 23 o C). S20
21 Figure S C{ 1 H} NMR spectrum of 4b (CDCl 3, 100 MHz, 23 o C). Figure S P NMR spectrum of complex 4b (CDCl 3, 162 MHz, 23 o C). S21
22 Figure S14. 1 H NMR spectrum of 4c (CDCl 3, 400 MHz, 23 o C). Figure S P NMR spectrum of complex 4c (CDCl 3, 162 MHz, 23 o C). S22
23 Figure S16. 1 H NMR spectrum of 5a (C 6 D 6- d 6, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 5a (C 6 D 6- d 6, 100 MHz, 23 o C). S23
24 Figure S P{ 1 H} NMR spectrum of 5a (C 6 D 6- d 6, 162 MHz, 23 o C). Figure S19. 1 H NMR spectrum of 5b (C 6 D 6- d 6, 400 MHz, 23 o C). S24
25 Figure S C{ 1 H} NMR spectrum of 5b (C 6 D 6- d 6, 100 MHz, 23 o C). Figure S P{ 1 H} NMR spectrum of 5b (C 6 D 6- d 6, 162 MHz, 23 o C). S25
26 Figure S22. 1 H NMR spectrum of 7a (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7a (CDCl 3, 100 MHz, 23 o C). S26
27 Figure S24. 1 H NMR spectrum of 7b (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7b (CDCl 3, 100 MHz, 23 o C). S27
28 Figure S26. 1 H NMR spectrum of 7c (CDCl 3, 100 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7c (CDCl 3, 100 MHz, 23 o C). S28
29 Figure S28. 1 H NMR spectrum of 7d (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7d (CDCl 3, 100 MHz, 23 o C). S29
30 Figure S30. 1 H NMR spectrum of 7e (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7e (CDCl 3, 100 MHz, 23 o C). S30
31 Figure S32. 1 H NMR spectrum of 7f (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7f (CDCl 3, 100 MHz, 23 o C). S31
32 Figure S34. 1 H NMR spectrum of 7g (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7g (CDCl 3, 100 MHz, 23 o C). S32
33 Figure S36. 1 H NMR spectrum of 7h (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7h (CDCl 3, 100 MHz, 23 o C). S33
34 Figure S38. 1 H NMR spectrum of 7i (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7i (CDCl 3, 100 MHz, 23 o C). S34
35 Figure S40. 1 H NMR spectrum of 7j (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7j (CDCl 3, 100 MHz, 23 o C). S35
36 Figure S42. 1 H NMR spectrum of 7k (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7k (CDCl 3, 100 MHz, 23 o C). S36
37 Figure S44. 1 H NMR spectrum of 7l (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7l (CDCl 3, 100 MHz, 23 o C). S37
38 Figure S46. 1 H NMR spectrum of 7m (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7m (CDCl 3, 100 MHz, 23 o C). S38
39 Figure S48. 1 H NMR spectrum of 7n (DMSO-d 6, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7n (DMSO-d 6, 100 MHz, 23 o C). S39
40 Figure S50. 1 H NMR spectrum of 7o (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7o (CDCl 3, 100 MHz, 23 o C). S40
41 Figure S52. 1 H NMR spectrum of 7p (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7p (CDCl 3, 100 MHz, 23 o C). S41
42 Figure S54. 1 H NMR spectrum of 7q (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7q (CDCl 3, 100 MHz, 23 o C). S42
43 Figure S56. 1 H NMR spectrum of 7r (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 7r (CDCl 3, 100 MHz, 23 o C). S43
44 Figure S58. 1 H NMR spectrum of 9a (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9a (CDCl 3, 100 MHz, 23 o C). S44
45 Figure S60. 1 H NMR spectrum of 9b (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9b (CDCl 3, 100 MHz, 23 o C). S45
46 Figure S62. 1 H NMR spectrum of 9c (DMSO-d 6, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9c (DMSO-d 6, 100 MHz, 23 o C). S46
47 Figure S64. 1 H NMR spectrum of 9d (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9d (CDCl 3, 100 MHz, 23 o C). S47
48 Figure S66. 1 H NMR spectrum of 9e (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9e (CDCl 3, 100 MHz, 23 o C). S48
49 Figure S68. 1 H NMR spectrum of 9f (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9f (CDCl 3, 100 MHz, 23 o C). S49
50 Figure S70. 1 H NMR spectrum of 9g (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9g (CDCl 3, 100 MHz, 23 o C). S50
51 Figure S72. 1 H NMR spectrum of 9h (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9h (CDCl 3, 100 MHz, 23 o C). S51
52 Figure S74. 1 H NMR spectrum of 9i (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9i (CDCl 3, 100 MHz, 23 o C). S52
53 Figure S76. 1 H NMR spectrum of 9j (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9j (CDCl 3, 100 MHz, 23 o C). S53
54 Figure S78. 1 H NMR spectrum of 9k (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9k (CDCl 3, 100 MHz, 23 o C). S54
55 Figure S80. 1 H NMR spectrum of 9l (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9l (CDCl 3, 100 MHz, 23 o C). S55
56 Figure S82. 1 H NMR spectrum of 9m (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9m (CDCl 3, 100 MHz, 23 o C). S56
57 Figure S84. 1 H NMR spectrum of 9n (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 9n (CDCl 3, 100 MHz, 23 o C). S57
58 Figure S86. 1 H NMR spectrum of 11a (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 11a (CDCl 3, 100 MHz, 23 o C). S58
59 Figure S88. 1 H NMR spectrum of 11b (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 11b (CDCl 3, 100 MHz, 23 o C). S59
60 Figure S90. 1 H NMR spectrum of 12a (DMSO-d 6, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 11b (DMSO-d 6, 100 MHz, 23 o C). S60
61 Figure S92. 1 H NMR spectrum of 12b (DMSO-d 6, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 12b (DMSO-d 6, 100 MHz, 23 o C). S61
62 Figure S94. 1 H NMR spectrum of 14a (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14a (CDCl 3, 100 MHz, 23 o C). S62
63 Figure S96. 1 H NMR spectrum of 14b (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14b (CDCl 3, 100 MHz, 23 o C). S63
64 Figure S98. 1 H NMR spectrum of 14c (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14c (CDCl 3, 100 MHz, 23 o C). S64
65 Figure S H NMR spectrum of 14d (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14d (CDCl 3, 100 MHz, 23 o C). S65
66 Figure S H NMR spectrum of 14e (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14e (CDCl 3, 100 MHz, 23 o C). S66
67 Figure S H NMR spectrum of 14f (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14f (CDCl 3, 100 MHz, 23 o C). S67
68 Figure S H NMR spectrum of 14g (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14g (CDCl 3, 100 MHz, 23 o C). S68
69 Figure S H NMR spectrum of 14h (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14h (CDCl 3, 100 MHz, 23 o C). S69
70 Figure S H NMR spectrum of 14i (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14i (CDCl 3, 100 MHz, 23 o C). S70
71 Figure S H NMR spectrum of 14j (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14j (CDCl 3, 100 MHz, 23 o C). S71
72 Figure S H NMR spectrum of 14k (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14k (CDCl 3, 100 MHz, 23 o C). S72
73 Figure S H NMR spectrum of 14l (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14l (CDCl 3, 100 MHz, 23 o C). S73
74 Figure S H NMR spectrum of 14m (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14m (CDCl 3, 100 MHz, 23 o C). S74
75 Figure S H NMR spectrum of 14n (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14n (CDCl 3, 100 MHz, 23 o C). S75
76 Figure S H NMR spectrum of 14o (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14o (CDCl 3, 100 MHz, 23 o C). S76
77 Figure S H NMR spectrum of 14p (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14p (CDCl 3, 100 MHz, 23 o C). S77
78 Figure S H NMR spectrum of 14q (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14q (CDCl 3, 100 MHz, 23 o C). S78
79 Figure S H NMR spectrum of 14r (CDCl 3, 400 MHz, 23 o C). Figure S C{ 1 H} NMR spectrum of 14r (CDCl 3, 100 MHz, 23 o C). S79
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Fused Bis-Benzothiadiazoles as Electron Acceptors
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Supporting Information File 2 Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ; Preparation, structures and host guest chemistry of fluorinated syn-bisquinoxaline molecular tweezers
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Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
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and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
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SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
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Supporting Information Chloroyttrium 2-(1-(arylimino)alkyl)quinolin-8-olate Complexes: Synthesis, Characterization, and Catalysis of the Ring-Opening Polymerization (ROP) of ε- Caprolactone (ε-cl) Wenjuan
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Palladium-Catalyzed Direct ortho-sulfonylation of. Azobenzenes with Arylsulfonyl Chlorides via C H. Table of Contents
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Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties
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SUPPORTING INFORMATION. Diastereoselective synthesis of nitroso acetals from (S,E)- -aminated
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Supporting Information. Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the. Synthesis of Heteroaromatic Biaryls
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Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: -S-aromatic heterocyclic podophyllum derivatives display antitumor activity
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Supporting Information [NH 3 CH 3 ] [In SbS 9 SH]: A novel methylamine-directed indium thioantimonate with Rb + ion-exchange property Kai-Yao Wang a,b, Mei-Ling Feng a, Jian-Rong Li a and Xiao-Ying Huang
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Supporting Information. for. A novel application of 2-silylated 1,3-dithiolanes for the. synthesis of aryl/hetaryl-substituted ethenes and
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ANNEXE 2 : SPECTRES DE RÉSONANCE MAGNÉTIQUE NUCLÉAIRE
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College of Life Science, Dalian Nationalities University, Dalian , PR China.
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