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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl Compounds: An Efficient Synthesis of rrocene-containing, -Unsaturated Esters Shufeng Chen,* Yan Du, Haiying Zhao, Baoguo Li* College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot , China address: shufengchen@imu.edu.cn, baoguol@sohu.com CNTENTS 1. General information...s2 2. General Procedure for the preparation of -ferrocenecarboxyl substituted diazo compounds S2 3. General Procedure for the Rh 2 (Ac) 4 -catalyzed reaction of 3a-j....S2 4. Spectral data for -ferrocenecarboxyl substituted diazo compounds 3....S3 5. Spectral data for 2,3-migration products s H and 13 C NMR spectra.....s10 S1
2 1. General information All reagents were used as received from commercial sources, unless specified otherwise, or prepared as described in the literature. All solvents were distilled under a nitrogen atmosphere prior to use. CH 2 2 was dried over CaH 2. For chromatography, mesh silica gel (Qingdao, China) was employed. H and 13 C NMR spectra were recorded at 500 MHz and 125 MHz FT-NMR spectrometer. Chemical shifts are reported in ppm using tetramethylsilane as internal standard when CD3 was used as solvent. IR spectra were recorded on a FT-IR instrument. The HRMS analysis was obtained on a GCTF mass spectrometer. Melting points were determined with melting points apparatus and are uncorrected General Procedure for the preparation of -ferrocenecarboxyl substituted diazo compounds 3 In a dried three-necked round-bottom flask, ferrocenoyl chloride (1.1 mmol) in 2 ml of anhydrous CH 2 2 was added dropwise to a solution of -hydroxy -diazo ester 2 (1.0 mmol) with pyridine (2.0 mmol) in 5 ml of anhydrous CH 2 2 at 0 under. The resulting mixture was stirred at 0 C and the progress of the reaction was monitored by TLC. After completion of the esterification reaction, saturated NaHC 3 was added at 0 C. the organic phase was dried using Na 2 S 4, and solvent was removed under reduced pressure. Next, the residue was subjected to chromatography on silica gel to afford the products 3a-j. 3. General Procedure for the Rh (Ac) -catalyzed reaction of 3a-j 2 4 In a dried three-necked round-bottom flask, Rh 2 (Ac) 4 (0.1 mol %) was dissolved into 5 ml of anhydrous CH 2 2. A solution of diazo substrates 3a-j in anhydrous CH 2 2 was added dropwise at 0 C over the course of 30 min. The reaction mixture was stirred until TLC analysis indicated the complete disappearance of the diazo compound. The solvent was then removed under reduced pressure, and the crude residue was purified 2,3-migration products. by column chromatography to give the corresponding S2
3 4. -ferrocenecarboxyl substituted diazo compounds 3 Red solid; Mp: o C; IR (KBr) 3110, 2098, 1701, 3a C 2 Et 1404, 1122, 1025, 829 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.29 (t, J = 7.0 Hz, 3H), 4.17 (s, 5H), 4.28 (q, J = 7.0 Hz, 2H), 4.44 (s, 2H), 4.88 (s, 2H), 6.98 (s, 1H), (m, 5H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.4, 70.0, 70.3, 70.5, 70.6, 71.7, 125.9, 128.6, 128.9, 136.9, 170.2; EI-MS (m/z, relative intensity): 404 [(M-28) +, 100]; Anal. calcd for C 22 H 20 4 : C, 61.13; H, 4.66; N, 6.48; Found: C, 61.35; H, 4.93; N, Red solid; Mp: o C; IR (KBr) 3110, 2104, 1715, 1121, 1005, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 3b C 2 Et 1.29 (t, J = 7.0 Hz, 3H), 4.18 (s, 5H), 4.28 (q, J = 7.0 Hz, 2H), 4.45 (t, J = 2.0 Hz, 2H), 4.87 (d, J = 2.0 Hz, 2H), 6.93 (s, 1H), 7.39 (s, 4H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.4, 69.4, 69.9, 70.2, 70.3, 71.7, 127.4, 129.1, 134.5, 135.5, 170.3; EI-MS (m/z, relative intensity): 438 [(M-28) +, 33], 461 (100); Anal. calcd for C 22 H 19 4 : C, 56.62; H, 4.10; N, 6.00; Found: C, 57.01; H, 4.09; N, Br Red solid; Mp: o C; IR (KBr) 3086, 2102, 1701, 1125, 1006, 819 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 3c C 2 Et 1.29 (t, J = 7.0 Hz, 3H), 4.18 (s, 5H), 4.28 (q, J = 7.0 Hz, 2H), 4.45 (t, J = 2.0 Hz, 2H), 4.87 (d, J = 2.0 Hz, 2H), 6.91 (s, 1H), 7.34 (d, J = 10.0 Hz, 2H), 7.55 (d, J = 10.0 Hz, 2H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.4, 69.5, 69.9, 70.3, 70.4, 71.8, 122.6, 127.6, 132.0, 136.0, 170.3; EI-MS (m/z, relative intensity): 465 (100), 505 [(M+Na-28) +, 58]; Anal. calcd for C 22 H 19 Br 4 : C, 51.69; H, 3.75; N, 5.48; Found: C, 51.80; H, 4.04; N, S3
4 Red solid; Mp: o C; IR (KBr) 3109, 2099, 3d C 2 Et 1708, 1113, 1025, 826 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.27 (t, J = 7.0 Hz, 3H), 4.20 (s, 5H), (m, 2H), 4.46 (t, J = 1.0 Hz, 2H), 4.90 (dd, J = 2.0 Hz, J = 1.0 Hz, 2H), 7.12 (s, 1H), (m, 2H), 7.44 (d, J = 1.5 Hz, 1H), 7.60 (d, J = 7.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.2, 68.4, 69.9, 70.2, 70.4, 71.7, 126.9, 127.4,129.7, 130.0, 132.1, 134.4, 170.3; EI-MS (m/z, relative intensity): 466 (M +, 73), 455 (100); Anal. calcd for C 22 H 19 4 : C, 56.62; H, 4.10; N, 6.00; Found: C, 57.00; H, 4.11; N, CH 3 Red solid; Mp: o C; IR (KBr) 3111, 2097, 1702, 1404, 1122, 1025, 829 cm -1 ; 1 H NMR (500 MHz, 3e C 2 Et CD 3 ) δ 1.29 (t, J = 7.0 Hz, 3H), 1.42 (s, 3H), 4.17 (s, 5H), 4.28 (q, J = 7.0 Hz, 2H), 4.43 (t, J = 1.5 Hz, 2H), 4.88 (dd, J = 2.0 Hz, J = 1.5 Hz, 2H), 6.99 (s, 1H), 7.44 (m, 4H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.6, 69.4, 69.6, 70.0, 70.2, 70.4, 72.0, 124.1, 126.9, 144.1, 147.9, 164.2, 170.5; EI-MS (m/z, relative intensity): 418 [(M-28) +, 8], 421 (100); Anal. calcd for C 23 H 22 4 : C, 61.90; H, 4.97; N, 6.28; Found: C, 62.23; H, 5.04; N, Red solid; Mp: o C; IR (KBr) 3115, 2101, 1714, 1606, 1118, 1003, 847 cm -1 ; 1 H NMR (500 MHz, 3f C 2 Et CD 3 ) δ 1.29 (t, J = 7.5 Hz, 3H), 4.20 (s, 5H), 4.28 (q, J = 7.5 Hz, 2H), 4.49 (t, J = 1.5 Hz, 2H), 4.90 (d, J = 2.0 Hz, 2H), 7.00 (s, 1H), 7.64 (d, J = 10.5 Hz, 2H), 8.28 (d, J = 10.5 Hz, 2H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.6, 69.3, 69.6, 70.0, 72.0, 124.1, 126.9, 144.1, 147.9, 164.2, 170.5; EI-MS (m/z, relative intensity): 477 (M +, 48), 499 (100); Anal. calcd for C 22 H 19 N 3 6 : C, 55.37; H, 4.01; N, 8.80; Found: C, 55.03; H, 4.11; N,8.71. S4
5 Red solid; Mp: o C; IR (KBr) 3108, 2096, 3g C 2 Et 1709, 1112, 1023, 850, 826 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.26 (t, J = 7.0 Hz, 3H), 4.21 (s, 5H), 4.26 (q, J = 7.0 Hz, 2H), 4.47 (s, 2H), 4.89 (d, J = 1.5 Hz, 2H), 7.40 (s, 1H), 7.54 (t, J = 7.0 Hz, 1H), 7.71 (t, J = 7.5 Hz, 1H), 7.89 (d, J = 7.0 Hz, 1H), 8.12 (d, J = 7.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 61.4, 70.0, 70.3, 70.4, 71.9, 72.0, 125.5, 128.9,129.6, 131.0, 132.5, 146.9, 167.8, 170.6; EI-MS (m/z, relative intensity): 449 [(M-28) +, 82], 494 (100); Anal. calcd for C 22 H 19 N 3 6 : C, 55.37; H, 4.01; N, 8.80; Found: C, 55.12; H, 4.10; N, h C 2 Et range solid; Mp: o C; IR (KBr) 3104, 2111, 1688, 1117, 1025, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.29 (t, J = 7.0 Hz, 3H), 4.18 (s, 5H), 4.26 (q, J = 7.0 Hz, 2H), 4.41 (s, 2H), 4.82 (s, 2H), 5.05 (s, 2H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 59.2, 61.1, 69.8, 70.1, 70.3, 71.6, 165.5, 172.6; EI-MS (m/z, relative intensity): 329 (100), 356 (M +, 45); Anal. calcd for C 16 H 16 4 : C, 53.96; H, 4.53; N, 7.78; Found: C, 53.61; H, 4.53; N, i CH 3 C 2 Et range oil; IR (KBr) 3104, 2103, 1763, 1712, 1127, 1004, 826 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.28 (t, J = 7.0 Hz, 3H), 1.59 (d, J = 7.0 Hz, 3H), 4.19 (s, 5H), 4.26 (q, J = 7.0 Hz, 2H), 4.40 (dt, J = 3.5 Hz, J = 1.5 Hz, 2H), 4.80 (dt, J = 15.5 Hz, J = 1.5 Hz, 2H), 5.90 (q, J = 7.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.5, 18.8, 61.1, 66.0, 69.9, 70.2, 70.8, 71.5, 165.0, 171.0; Anal. calcd for C 17 H 18 4 : C, 55.16; H, 4.90; N, 7.57; Found: C, 55.39; H, 4.72; N, S5
6 3j CH2CH2CH3 C 2 Et range oil; IR (KBr) 3101, 2101, 1712, 1099, 1024, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.00 (t, J = 7.5 Hz, 3H), 1.27 (t, J = 7.0 Hz, 3H), (m, 2H), (m, 1H), (m, 1H), 4.18 (s, 5H), 4.24 (q, J = 7.0 Hz, 2H), 4.40 (dd, J = 4.0 Hz, J = 1.5 Hz, 2H), 4.81 (dt, J = 13.0 Hz, J = 1.5 Hz, 2H), 5.72 (t, J = 7.5 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 13.6, 14.5, 18.9, 34.1, 61.0, 69.4, 69. 8, 70.2, 71.8, 71.4, 165.0, 171.1; EI-MS (m/z, relative intensity): 370 (100), 384 (M +, 7); Anal. calcd for C 19 H 22 4 : C, 57.30; H, 5.57; N, 7.03; Found: C, 57.55; H, 5.53; N, Spectral data for 2,3-migration products 4Ea Et Ph range oil; IR (KBr), 1724, 1105, 1022, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.13 (t, J = 7.0 Hz, 3H), 4.22 (q, J = 7.0 Hz, 2H), 4.37 (s, 5H), 4.49 (d, J = 2.0 Hz, 2H), 4.92 (t, J = 2.0 Hz, 2H), 6.90 (s, 1H), (m, 5H); 13 C NMR (125 MHz, CD 3 ) δ 13.7, 61.4, 69.1, 70.1, 70.6, 72.0, 127.9, 128.0, 128.4, 129.2, 132.7, 138.5, 162.5, 170.4; EI-MS (m/z, relative intensity): 404 (M +, 100); Anal. calcd for C 22 H 20 4 : C, 65.37; H, 4.99; Found: C, 65.66; H, Eb Et range solid; Mp: o C; IR (KBr), 1725, 1098, 1011, 849, 810 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.17 (t, J = 7.0 Hz, 3H), 4.22 (q, J = 7.0 Hz, 2H), 4.36 (s, 5H), 4.50 (t, J = 2.0 Hz, 2H), 4.91 (t, J = 2.0 Hz, 2H), 6.82 (s, 1H), (m, 4H); 13 C NMR (125 MHz, CD 3 ) δ 13.8, 61.5, 68.9, 70.1, 70.6, 72.1, 126.9, 128.2, 130.6, 131.1, 134.4, 138.8, 162.2, 170.4; EI-MS (m/z, relative intensity): 438 (M +, 100); Anal. calcd for C 22 H 19 4 : C, 60.23; H, 4.37; Found: C,60.52; H, S6
7 Et range solid; Mp: o C; IR (KBr), 1725, 1098, 1010, 849, 810 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.37 (t, J = 7.0 Hz, 3H), 4.36 (m, 7H), 4.54 (t, J = 1.5 Hz, 2H), Zb (t, J = 1.5 Hz, 2H), 7.27 (s, 1H), (m, 4H); 13 C NMR (125 MHz, CD 3 ) δ 14.3, 61.8, 69.2, 70.2, 70.6, 72.1, 125.4, 129.0, 130.8, 131.4, 135.5, 137.8, 162.5, 169.4; EI-MS (m/z, relative intensity): 438 (M +, 100); Anal. calcd for C H 19 4 : C, 60.23; H, 4.37; Found: C,60.47; H, 4Ec Et Br range solid; Mp: C; IR (KBr), 1725, 1100, 1007, 824 cm ; H NMR (500 MHz, CD3) δ 1.17 (t, J = 7.0 Hz, 3H), 4.22 (q, J = 7.0 Hz, 2H), 4.36 (s, 5H), 4.50 (t, J = 2.0 Hz, 2H), 4.91 o -1 1 (t, J = 2.0 Hz, 2H), 6.80 (s, 1H), 7.27 (t, J = 7.0 Hz, 2H), 7.47 (d, J = 10.5 Hz, 2H); 13 C NMR (125 MHz, CD 3 ) δ 13.8, 61.5, 68.9, 70.1, 70.6, 72.1, 122.6, 126.9, 130.9, 131.2, 131.6, 138.8, 162.2, 170.4; EI-MS (m/z, relative intensity): 482 (M +, 100); Anal. calcd for C 22 H 19 Br4: C, 54.69; H, 3.96; Found: C, 54.49; H, Et 4Ed range oil; IR (KBr), 1727, 1102, 1022, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ1.38 (t, J = 7.0 Hz, 3H), 4.30 (s, 5H), 4.36 (q, J = 7.0 Hz, 2H), 4.49 (t, J = 2.0 Hz, 2H), 4.90 (t, J = 2.0 Hz, 2H), (m, 2H), (m, 1H), 6.69 (s, 1H), 7.80 (q, J = 7.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.3, 61.9, 69.1, 70.1, 70.6, 72.0, 122.8, 126.7, 129.8, 130.4, 130.5, 130.6, 134.7, 138.8, 162.4, 169.5; EI-MS (m/z, relative intensity): 438 (M +, 100); Anal. calcd for C 22 H 19 4 : C, 60.23; H, 4.37; Found: C, 60.44; H, S7
8 Et CH 3 range oil; IR (KBr), 1724, 1104, 1022, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.13 (t, J = 7.0 Hz, 3H), 1.25 (s, 3H), 4.20 (q, J = 7.0 Hz, 4Ee 2H), 4.37 (s, 5H), 4.50 (t, J = 1.5 Hz, 2H), 4.92 (t, J = 1.5 Hz, 2H), 6.90 (s, 1H), (m, 4H); 13 C NMR (125 MHz, CD 3 ) δ 13.7, 29.7, 61,4, 69.1, 70.1, 70.6, 72.0, 127.9, 128.0, 128.4, 129.2, 132.7, 138.5, 162.5, 170.4; EI-MS (m/z, relative intensity): 418 (M +, 5), 381 (100); Anal. calcd for C 23 H 22 4 : C, 66.05; H, 5.30; Found: C, 65.94; H, Eg Et 2 N range oil; IR (KBr), 1727, 1101, 1021, 824 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.38 (t, J = 7.0 Hz, 3H), 4.23 (s, 5H), 4.37 (q, J = 7.0 Hz, 2H), 4.46 (t, J = 1.5 Hz, 2H), 4.81 (t, J = 1.5 Hz, 2H), (m, 1H), (m, 2H), 7.75 (s, 1H), 8.10 (d, J = 8.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.2, 62.1, 68.7, 70.1, 70.6, 72.1, 123.2, 124.9, 127.7, 129.7, 131.1, 133.2, 139.4, 148.0, 161.8, 170.0; EI-MS (m/z, relative intensity): 449 (M +, 100); Anal. calcd for: C 22 H 19 N 6 : C, 58.82; H, 4.26; N, 3.12; Found: C, 59.17; H, 4.51; N, h Et range oil; IR (KBr) 3106, 1732, 1647, 1107, 1024, 825 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.35 (t, J = 7.0 Hz, 3H), 4.32 (q, J = 7.0 Hz, 2H), 4.35 (s, 5H), 4.47 (s, 2H), 4.88 (s, 2H), 5.50 (s, 1H), 6.08 (s, 1H); 13 C NMR (125 MHz, CD 3 ) δ 14.2, 61.7, 69.2, 70.1, 70.6, 71.9, 113.6, 144.9, 161.7, 169.9; EI-MS (m/z, relative intensity): 328 (M +, 42), 346 (100); Anal. calcd for C 16 H 16 4 : C, 58.56; H, 4.91; Found: C, 58.81; H, S8
9 4i Et CH 3 range solid; Mp: o C; IR (KBr) 3106, 1720, 1118, 1022, 822 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 1.34 (t, J = 7. 0 Hz, 3H), 2.12 (d, J = 7.5 Hz, 3H), (m, 7H), 4.46 (t, J = 2.0 Hz, 2H), 4.87 (t, J = 2.0 Hz, 2H), 6.05 (q, J = 7.5 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 13.0, 14.3, 61.1, 69.6, 70.0, 70.5, 71.8, 128.6, 138.3, 162.3, 170.6; EI-MS (m/z, relative intensity): 342 (M +, 100); Anal. calcd for C 17 H 18 4 : C, 59.67; H, 5.30; Found: C, 59.95; H, j Et CH 2 CH 2 CH 3 range oil; IR (KBr) 3106, 1726, 1122, 1025, 823 cm -1 ; 1 H NMR (500 MHz, CD 3 ) δ 0.98 (t, J = 7.5 Hz, 3H), 1.33 (t, J = 7.0 Hz, 3H), 1.51 (q, J = 7.0 Hz, 2H), 2.58 (q, J = 7.5 Hz, 2H), (m, 7H), 4.45 (t, J = 2.0 Hz, 2H), 4.87 (t, J = 2.0 Hz, 2H), 5.96 (t, J = 8.0 Hz, 1H); 13 C NMR (125 MHz, CD 3 ) δ 13.8, 14.3, 22.5, 29.0, 61.2, 69.7, 70.1, 70.6, 71.8, 133.7, 137.7, 162.4, 170.6; EI-MS (m/z, relative intensity): 356 (M +, 4), 387 (100); Anal. calcd for C 19 H 22 4 : C, 61.64; H, 5.99; Found: C, 61.35; H, S9
10 6. 1 H and 13 CNMR spectra 3a C 2 Et 3a C 2 Et S10
11 3b C 2 Et 3b C 2 Et S11
12 Br 3c C 2 Et Br 3c C 2 Et S12
13 3d C 2 Et 3d C 2 Et S13
14 CH 3 3e C 2 Et CH 3 3e C 2 Et S14
15 3f C 2 Et 3f C 2 Et S15
16 3g C 2 Et 3g C 2 Et S16
17 3h C 2 Et 3h C 2 Et S17
18 CH 3 C 2 Et 3i CH 3 C 2 Et 3i S18
19 CH 2 CH 2 CH 3 C 2 Et 3j CH 2 CH 2 CH 3 C 2 Et 3j S19
20 Et Ph 4Ea Et Ph 4Ea S20
21 Et 4Eb Et 4Eb S21
22 Et 4Zb Et 4Zb S22
23 Et 4Ec Br Et 4Ec Br S23
24 Et 4Ed Et 4Ed S24
25 Et 4Ee CH 3 Et 4Ee CH 3 S25
26 Et 2 N 4Eg 4Eg Et 2 N S26
27 4h Et Et 4h S27
28 Et 4i CH 3 Et 4i CH 3 S28
29 Et 4j CH 2 CH 2 CH 3 Et 4j CH 2 CH 2 CH 3 S29
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*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3
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Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 Supporting Information Palladium-Catalyzed Construction of Spirooxindoles by Arylative Cyclization of 3-( -Disubstituted)allylidene-2-Oxindoles
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Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
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hydroxyanthraquinones related to proisocrinins
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