Supporting Information Manganese-Catalyzed Aerobic ...
Supporting Information Manganese-Catalyzed Aerobic ... Supporting Information Manganese-Catalyzed Aerobic ...
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013 dimethyl 2-(3-(1-methyl-1H-indol-3-yl)propyl)malonate (1e) 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, 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 Hz), 2.80 (2H, t, J = 7.6 Hz), 1.92 (2H, m), 0.92 (9H, s), 0.064 (6H, s) ; 13 C NMR (CDCl 3 ): = 170.00, 137.12, 127.84, 126.26, 121.53, 118.63, 114.35, 109.22, 52.52, 51.70, 32.63, 28.78, 28.05, 24.77; HRMS (ESI): m/z calcd for C 17 H 21 NO 4 Na [M+Na] + 326.1368. Found 326.1355. dimethyl 2-(2-(1H-indol-3-yl)ethyl)malonate (1f) 1 H NMR (CDCl 3 ): δ =7.60 (1H, d, J = 8.0 Hz), 7.35 (1H, d, J = 8.0 Hz), 7.18 (1H, t, J = 7.0 Hz), 7.13 (1H, t, J = 7.0 Hz), 7.01 (1H, s), 3.72 (6H, s), 3.46 (1H, t, J = 8.3 Hz), 2.82 (2H, t, J = 8.3 Hz), 2.33 (2H, q, J = 7.1 Hz); 13 C NMR (CDCl 3 ): = 170.07, 136.41, 127.25, 121.25, 119.95, 118.77, 114.34, 111.25, 52.53, 52.42, 51.20, 29.31, 22.86; HRMS (ESI): m/z calcd for C 15 H 17 NO 4 Na [M+Na] + 298.1055. Found 298.1068. dimethyl 2-(4-(1H-indol-3-yl)butyl)malonate (1g) 1 H NMR (CDCl 3 ): δ =7.58 (1H, d, J = 8.2 Hz), 7.35 (1H, d, J = 8.1 Hz), 7.17 (1H, t, J = 8.1 Hz), 7.10 (1H, t, J = 8.1 Hz), 6.97 (1H, s), 3.72 (6H, s), 3.36 (1H, t, J = 7.4 Hz), 2.76 (2H, t, J = 7.2 Hz), 1.97 (2H, m), 1.74 (2H, m), 1.42 (2H, m); 13 C NMR (CDCl 3 ): = 170.11, 136.45, 127.58, 121.93, 121.28, 119.17, 118.49, 116.49, 111.17, 52.57, 51.80, 29.73, 28.84, 27.30, 24.90; HRMS (ESI): m/z calcd for C 17 H 21 NO 4 Na [M+Na] + 326.1368. Found 326.1369. dimethyl 2-(2-(1H-indol-1-yl)ethyl)malonate (1h) 1 H NMR (CDCl 3 ): δ =7.62 (1H, d, J = 7.5 Hz), 7.33 (1H, d, J = 8.1 Hz), 7.22 (1H, t, J = 8.0 Hz), 7.11 (1H, t, J = 7.1 Hz), 7.07 (1H, s), 6.50 (1H, s), 4.23 (2H, t, J = 7.1 Hz), 3.73 (6H, s), 3.31 (1H, t, J = 7.1 Hz), 2.44 (2H, dt, J = 7.1, 7.1 Hz); 13 C NMR (CDCl 3 ): = 169.20, 135.92, 128.70, 127.77, 121.71, 121.06, 119.55, 109.31, 101.72, 52.72, 48.74, 43.72, 29.28; HRMS (ESI): m/z calcd for C 15 H 17 NO 4 Na [M+Na] + 298.1055. Found 298.1044. dimethyl 2-(3-(1H-indol-1-yl)propyl)malonate (1i) 1 H NMR (CDCl 3 ): δ =7.63 (1H, d, J = 8.0 Hz), 7.32 (1H, d, J = 8.0 Hz), 7.20 (1H, t, J = 7.4 Hz), 7.09 (1H, m), 6.49 (1H, s), 4.15 (2H, t, J = 7.2 Hz), 3.70 (6H, s), 3.34 (1H, t, J = 7.2 Hz), 1.91 (4H, m); 13 C NMR (CDCl 3 ): = 169.53, 135.92, 128.74, 127.77, 121.59, 121.11, 119.42, 109.32, 101.38, 52.68, 51.22, 45.96, 27.94, 26.26; HRMS (ESI): m/z calcd for C 16 H 19 NO 4 Na [M+Na] + 312.1212. Found 312.1202. 10
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2013 dimethyl 2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2a) 1 H NMR (CDCl 3 ): δ =7.52 (1H, d, J = 7.6 Hz), 7.34 (1H, d, J = 8.5 Hz), 7.19 (1H, t, J = 5.8 Hz), 7.01 (1H, t, J = 7.2 Hz), 3.78 (6H, s), 2.77 (2H, t, J = 6.3 Hz), 2.46 (2H, m), 1.97 (2H, m); 13 C NMR (CDCl 3 ): = 170.61, 136.29, 127.29, 126.70, 122.66, 119.39, 118.84, 113.90, 111.15, 55.36, 53.28, 31.09, 20.75, 20.59; HRMS (ESI): m/z calcd for C 16 H 17 NO 4 Na [M+Na] + 310.1055. Found 310.1069. dimethyl 6-bromo-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2b) 1 H NMR (CD 3 OD): δ =7.55 (1H, s), 7.26 (1H, d, J = 8.6 Hz), 7.17 (1H, d, J = 8.6 Hz), 3.77 (6H, s), 2.70 (2H, t, J = 5.8 Hz), 2.41 (2H, m), 1.93 (2H, m), 1.25 (2H, t, J = 7.5 Hz); 13 C NMR (CDCl 3 ): = 170.35, 134.86, 128.69, 128.45, 125.37, 121.48, 113.51, 112.63, 112.54, 55.29, 53.38, 31.02, 30.91, 20.58, 20.44; HRMS (ESI): m/z calcd for C 16 H 16 BrNO 4 Na [M+Na] + 388.0160. Found 388.0136. dimethyl 8-bromo-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2c) 1 H NMR (CDCl 3 ): δ =7.45 (1H, d, J = 8.0 Hz), 7.34 (1H, d, J = 7.5 Hz), 6.99 (1H, t, J = 8.0 Hz), 3.81 (1H, s), 2.74 (2H, t, J = 6.3 Hz), 2.46 (2H, m), 1.96 (2H, m); 13 C NMR (CDCl 3 ): = 170.31, 135.05, 128.16, 127.94, 125.07, 120.61, 118.10, 115.17, 104.74, 55.33, 53.44, 31.07, 20.93, 20.44; HRMS (ESI): m/z calcd for C 16 H 16 BrNO 4 Na [M+Na] + 388.0160. Found 388.0143. dimethyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2d) 1 H NMR (CDCl 3 ): δ =7.24 (1H, d, J = 8.6 Hz), 6.94 (1H, s), 6.86 (1H, d, J = 6.3 Hz), 3.85 (3H, s), 3.78 (6H, s), 2.71 (2H, t, J = 6.3 Hz), 2.45 (2H, m), 1.97 (2H, m); 13 C NMR (CDCl 3 ): = 170.62, 154.07, 131.49, 128.08, 127.04, 113.64, 112.86, 111.96, 100.79, 56.10, 55.44, 53.30, 31.09, 31.09, 20.84, 20.60; HRMS (ESI): m/z calcd for C 17 H 19 BrNO 5 Na [M+Na] + 340.1161 Found 340.1165. dimethyl 9-methyl-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2e) 1 H NMR (CDCl 3 ): δ =7.51 (1H, d, J = 8.1 Hz), 7.31 (1H, d, J = 8.6 Hz), 7.24 (1H, d, J = 7.5 Hz), 7.10 (1H, t, J = 8.1 Hz), 3.78 (6H, s), 3.64 (3H, s), 2.81 (2H, t, J = 6.3 Hz), 2.50 (2H, m), 1.95 (2H, m); 13 C NMR (CDCl 3 ): = 171.24, 137.89, 129.91, 126.06, 122.44, 119.10, 118.83, 112.68, 109.19, 56.23, 53.19, 33.89, 31.03, 21.04, 20.64 ; HRMS (ESI): m/z calcd for C 17 H 19 NO 4 Na [M+Na] + 324.1212. Found 324.1222. dimethyl 1,4-dihydrocyclopenta[b]indole-3,3(2H)-dicarboxylate (2f) 1 H NMR (CDCl 3 ): δ =7.47 (1H, d, J = 8.0 Hz), 7.36 (1H, d, J = 8.0 Hz), 7.18 (1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 6.9 Hz), 3.77 (1H, s), 3.11 (2H, t, J = 5.8 Hz), 2.94 (2H, t, J = 6.9 Hz), 2.94 (2H, t, J = 6.3Hz); HRMS (ESI): m/z calcd for C 15 H 15 NO 4 Na [M+Na] + 296.0899. Found 296.0898. 11
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Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry<br />
This journal is © The Royal Society of Chemistry 2013<br />
dimethyl 2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2a)<br />
1 H NMR (CDCl 3 ): δ =7.52 (1H, d, J = 7.6 Hz), 7.34 (1H, d, J = 8.5 Hz), 7.19<br />
(1H, t, J = 5.8 Hz), 7.01 (1H, t, J = 7.2 Hz), 3.78 (6H, s), 2.77 (2H, t, J = 6.3 Hz),<br />
2.46 (2H, m), 1.97 (2H, m); 13 C NMR (CDCl 3 ): = 170.61, 136.29, 127.29,<br />
126.70, 122.66, 119.39, 118.84, 113.90, 111.15, 55.36, 53.28, 31.09, 20.75,<br />
20.59; HRMS (ESI): m/z calcd for C 16 H 17 NO 4 Na [M+Na] + 310.1055. Found 310.1069.<br />
dimethyl 6-bromo-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2b)<br />
1 H NMR (CD 3 OD): δ =7.55 (1H, s), 7.26 (1H, d, J = 8.6 Hz), 7.17 (1H, d,<br />
J = 8.6 Hz), 3.77 (6H, s), 2.70 (2H, t, J = 5.8 Hz), 2.41 (2H, m), 1.93 (2H,<br />
m), 1.25 (2H, t, J = 7.5 Hz); 13 C NMR (CDCl 3 ): = 170.35, 134.86, 128.69,<br />
128.45, 125.37, 121.48, 113.51, 112.63, 112.54, 55.29, 53.38, 31.02, 30.91,<br />
20.58, 20.44; HRMS (ESI): m/z calcd for C 16 H 16 BrNO 4 Na [M+Na] + 388.0160. Found 388.0136.<br />
dimethyl 8-bromo-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2c)<br />
1 H NMR (CDCl 3 ): δ =7.45 (1H, d, J = 8.0 Hz), 7.34 (1H, d, J = 7.5 Hz), 6.99<br />
(1H, t, J = 8.0 Hz), 3.81 (1H, s), 2.74 (2H, t, J = 6.3 Hz), 2.46 (2H, m), 1.96 (2H,<br />
m); 13 C NMR (CDCl 3 ): = 170.31, 135.05, 128.16, 127.94, 125.07, 120.61,<br />
118.10, 115.17, 104.74, 55.33, 53.44, 31.07, 20.93, 20.44; HRMS (ESI): m/z<br />
calcd for C 16 H 16 BrNO 4 Na [M+Na] + 388.0160. Found 388.0143.<br />
dimethyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2d)<br />
1 H NMR (CDCl 3 ): δ =7.24 (1H, d, J = 8.6 Hz), 6.94 (1H, s), 6.86 (1H, d,<br />
J = 6.3 Hz), 3.85 (3H, s), 3.78 (6H, s), 2.71 (2H, t, J = 6.3 Hz), 2.45 (2H,<br />
m), 1.97 (2H, m); 13 C NMR (CDCl 3 ): = 170.62, 154.07, 131.49, 128.08,<br />
127.04, 113.64, 112.86, 111.96, 100.79, 56.10, 55.44, 53.30, 31.09, 31.09,<br />
20.84, 20.60; HRMS (ESI): m/z calcd for C 17 H 19 BrNO 5 Na [M+Na] + 340.1161 Found 340.1165.<br />
dimethyl 9-methyl-2,3,4,9-tetrahydro-1H-carbazole-1,1-dicarboxylate (2e)<br />
1 H NMR (CDCl 3 ): δ =7.51 (1H, d, J = 8.1 Hz), 7.31 (1H, d, J = 8.6 Hz), 7.24<br />
(1H, d, J = 7.5 Hz), 7.10 (1H, t, J = 8.1 Hz), 3.78 (6H, s), 3.64 (3H, s), 2.81 (2H,<br />
t, J = 6.3 Hz), 2.50 (2H, m), 1.95 (2H, m); 13 C NMR (CDCl 3 ): = 171.24,<br />
137.89, 129.91, 126.06, 122.44, 119.10, 118.83, 112.68, 109.19, 56.23, 53.19,<br />
33.89, 31.03, 21.04, 20.64 ; HRMS (ESI): m/z calcd for C 17 H 19 NO 4 Na [M+Na] + 324.1212. Found 324.1222.<br />
dimethyl 1,4-dihydrocyclopenta[b]indole-3,3(2H)-dicarboxylate (2f)<br />
1 H NMR (CDCl 3 ): δ =7.47 (1H, d, J = 8.0 Hz), 7.36 (1H, d, J = 8.0 Hz), 7.18<br />
(1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 6.9 Hz), 3.77 (1H, s), 3.11 (2H, t, J = 5.8 Hz),<br />
2.94 (2H, t, J = 6.9 Hz), 2.94 (2H, t, J = 6.3Hz); HRMS (ESI): m/z calcd for<br />
C 15 H 15 NO 4 Na [M+Na] + 296.0899. Found 296.0898.<br />
11
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