Supporting Information Manganese-Catalyzed Aerobic ...
Supporting Information Manganese-Catalyzed Aerobic ...
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Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry<br />
This journal is © The Royal Society of Chemistry 2013<br />
7-bromo-3-(3-bromopropyl)-1H-indole (S4c)<br />
1 H NMR (CDCl 3 ): δ =7.56 (1H, d, J = 8.2 Hz), 7.35 (1H, d, J = 7.1 Hz), 7.10 (1H, s),<br />
7.00 (1H, t, J = 8.2 Hz), 3.43 (2H, t, J = 7.3 Hz), 2.93 (2H, t, J = 7.2 Hz), 2.24 (2H, m);<br />
13 C NMR (CDCl 3 ): = 135.07, 128.59, 124.44, 122.43, 120.59, 118.16, 115.95, 104.88,<br />
33.70, 32.85, 23.54; HRMS (ESI): m/z calcd for C 11 H 11 Br 2 NNa [M+Na] + 337.9156<br />
(51%), 339.9136 (100%). Found 339.9130.<br />
3-(3-bromopropyl)-5-methoxy-1H-indole (S4d)<br />
1 H NMR (CDCl 3 ): δ =7.24 (1H, m), 7.05-7.02 (2H, m), 6.88 (1H, d, J = 6.2 Hz),<br />
3.86 (3H, s), 3.45 (2H, t, J = 6.2 Hz), 2.91 (2H, t, J = 7.1 Hz), 2.23 (2H, m); 13 C<br />
NMR (CDCl 3 ): = 154.04, 131.62, 127.86, 122.71, 114.46, 112.29, 111.99,<br />
100.84, 56.09, 34.00, 32.96, 23.40; HRMS (ESI): m/z calcd for C 12 H 14 BrNONa<br />
[M+Na] + 290.0157. Found 290.0166.<br />
3-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-indole (S5)<br />
1 H NMR (CDCl 3 ): δ =7.61 (1H, d, J = 8.1 Hz), 7.35 (1H, d, J = 8.5 Hz), 7.18 (1H, t,<br />
J = 7.2 Hz), 7.11 (1H, t, J = 8.2 Hz), 6.99 (1H, s), 3.70 (2H, t, J = 6.3 Hz), 2.82 (2H, t,<br />
J = 8.2 Hz), 1.94 (2H, m), 0.92 (9H, s), 0.065 (6H, s); 13 C NMR (CDCl 3 ): = 136.43,<br />
127.67, 121.89, 121.31, 119.13, 119.05, 116.35, 111.16, 62.91, 33.29, 26.13, 21.41,<br />
18.49, -5.09; HRMS (ESI): m/z calcd for C 17 H 27 NOSiNa [M+Na] + 312.1760. Found 312.1750.<br />
3-(3-((tert-butyldimethylsilyl)oxy)propyl)-1-methyl-1H-indole (S6)<br />
1 H NMR (CDCl 3 ): δ =7.60 (1H, d, J = 7.1 Hz), 7.30 (1H, d, J = 8.5 Hz), 7.19 (1H, t,<br />
J = 7.1 Hz), 7.07 (1H, t, J = 6.7 Hz), 6.83 (1H, s), 3.74 (3H, s), 3.69 (2H, t, J = 6.2<br />
Hz), 2.80 (2H, t, J = 7.6 Hz), 1.92 (2H, m), 0.92 (9H, s), 0.064 (6H, s); 13 C NMR<br />
(CDCl 3 ): = 137.17, 128.10, 126.17, 121.52, 119.20, 118.59, 115.02, 109.17, 62.89,<br />
33.60, 32.59, 26.14, 21.37, 18.49, -5.08; HRMS (ESI): m/z calcd for C 18 H 19 NOSiNa [M+Na] + 326.1916.<br />
Found 326.1925.<br />
3-(1-methyl-1H-indol-3-yl)propan-1-ol (S7)<br />
1 H NMR (CDCl 3 ): δ =7.60 (1H, d, J = 8.2 Hz), 7.28 (1H, d, J = 8.2 Hz), 7.22 (1H, t, J<br />
= 7.1 Hz), 7.10 (1H, t, J = 7.1 Hz), 6.85 (1H, s), 3.72 (2H, t, J = 6.4 Hz), 2.85 (2H, t, J =<br />
7.2 Hz), 1.98 (2H, m); 13 C NMR (CDCl 3 ): = 137.11, 127.90, 126.23, 121.53, 119.02,<br />
118.63, 114.47, 109.21, 62.54, 33.18, 32.53, 21.30; HRMS (ESI): m/z calcd for<br />
C 12 H 15 NONa [M+Na] + 212.1051. Found 212.1048.<br />
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