phase: synthesis of biaryls, terphenyls and polyaryls
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1 Supporting Information for Studies on Pd/NiFe 2 O 4 catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls Sanjay R. Borhade and Suresh B. Waghmode* Address: Department of Chemistry, University of Pune, Ganeshkhind, Pune , India Suresh B. Waghmode - suresh@chem.unipune.ac.in Phone (extension) 545 and 585; Fax *Corresponding author Characterization data of the catalyst and of the products 1 29 Content Page No 1. Figure 1: Scanning electron microscope image for the Pd/NiFe 2 O Figure 2: The X-ray photoemission spectra of Pd/NiFe 2 O Figure 3: Effect of various concentrations on the Suzuki coupling reaction Figure 4: X-ray diffraction pattern for the fresh and spent Pd/NiFe 2 O 4 catalyst Table 1: Recycling of Pd/NiFe 2 O Characterization data of the products References... 16
2 1. Figure 1: Scanning electron microscope image for the Pd/NiFe 2 O 4.
3 2. Figure 2: The X-ray photoemission spectrum of Pd/NiFe 2 O 4. Intensity / Countes per second Pd 3d 5/ ev Pd 3d 3/ ev Binding Energy (ev)
4 3. Figure 3: Effect of various concentrations on the Suzuki coupling reaction [a]. 100 Concentration % conc conc conc conc conc conc conc conc Time (min) [a] Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1.2 mmol), base (2 mmol), 4 ml of 1:1 H 2 O/DMF, at 90 C and at different Pd concentrations.
5 4. Figure 4: X-ray diffraction pattern for the fresh and spent Pd/NiFe 2 O 4 catalyst. Spent Pd/NiFe 2 O 4 Intensity (a.u.) Fresh Pd/NiFe 2 O 4 (311) (511) (400) (440) (220) theta (degs.)
6 5. Table 1: Recycling of Pd/NiFe 2 O 4 for the Suzuki reaction of iodobenzene with phenylboronic acid a Entry Catalyst Time (min) % Conversion b 1 first cycle second cycle third cycle fourth cycle fifth cycle a Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1.2 mmol), Na 2 CO 3 (2 mmol), 4 ml of 1:1 H 2 O/DMF and Pd/NiFe 2 O 4 (0.1 mol %) at 90 C. b Conversions were determined by GC ( rel = ±5 %).
7 6. Characterization data for the products Biphenyl [1, , Ref. 1] 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 2H), 7.40 (t, 4H, J = 7.1 Hz), 7.54 (d, 4H, J = 7.1 Hz), 13 C NMR (75 MHz, CDCl 3, TMS): δ 127.0, 127.1, 128.6, FTIR (KBr, cm 1 ): 1429, 1479, MS (EI): m/z 154 (M + ). 3-(Hydroxymethyl)biphenyl [2, , Ref. 2] 1 H NMR (300 MHz, CDCl 3, TMS): δ 2.29 (s, 1H), 4.66 (s, 2H), (m, 9H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 65.1, 125.6, 125.7, 126.2, 127.0, 127.2, 128.6, 128.8, 140.7, 141.1, FTIR (KBr, cm 1 ): 1186, 1454, 1477, MS (EI): m/z 184 (M + ). 3-Carbethoxybiphenyl [3, , Ref. 3] COOEt 1 H NMR (300 MHz, CDCl 3, TMS): δ 1.43 (t, 3H, J = 7.1 Hz), 4.41 (q, 2H, J = 7.1 Hz), (m, 4H), 7.61 (d, 2H, 7.7 Hz), 7.77 (d, 1H, J = 7.7 Hz), 8.01 (d, 1H, J = 7.7 Hz) 8.27 (s, 1H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 14.4, 61.0, 127.0, 127.6, 128.1, 128.2, 128.7, 128.7, 130.9, 131.3, 140.0, 141.2, FTIR (KBr, cm 1 ): 2982, 1718, 1593, 1301, MS (EI): m/z 226 (M + ). 3-Aminobiphenyl [4, , Ref. 4] NH 2 1 H NMR (300 MHz, CDCl 3 +2 drops of DMSO-d 6, TMS): δ 3.78 (bs, 2H), 6.67 (d, 1H, J = 7.1 Hz), 6.92 (d, 1H, J = 6.6 Hz), 6.93 (s, 1H), 7.17 (t, 1H, J = 7.9 Hz), 7.29 (d, 1H, J = 7.1 Hz) 7.38 (t, 2H, J = 7.7 Hz), 7.52 (d, 2H, J = 7.1 Hz). 13 C NMR
![2] 1 H NMR (300 MHz, CDCl 3, TMS): δ 2.29 (s, 1H), 4.66 (s, 2H), 7.25 7.55 (m, 9H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 65.1, 125.6, 125.7, 126.2, 127.0, 127.2, 128.6, 128.8, 140.7, 141.1, 141.3. FTIR (KBr, cm 1 ): 1186, 1454, 1477, 3313-3381.](/docs-images/50/20254583/images/page_7.jpg "MS (EI): m/z 184 (M + ). 3-Carbethoxybiphenyl [3, 19926-50-2, Ref. 3] COOEt 1 H NMR (300 MHz, CDCl 3, TMS): δ 1.43 (t, 3H, J = 7.1 Hz), 4.41 (q, 2H, J = 7.1 Hz), 7.38 7.47 (m, 4H), 7.61 (d, 2H, 7.")
8 (75 MHz, CDCl 3 +2 drops of DMSO-d 6, TMS): δ 113.0, 113.6, 116.2, 125.8, 126.2, 127.6, 128.6, 140.1, 140.9, FTIR (neat, cm 1 ): 3446, 3369, 3054, 1618, 1575, 1481, 1317, MS (EI): m/z 169 (M + ). 2-Amino-5-phenylpyrimidine [5, , Ref. 5] N N NH 2 1 H NMR (300 MHz, CDCl 3, TMS): δ 5.60 (bs, 2H), (m, 5H), 8.52 (s, 2H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 124.6, 125.8, , 129.0, 135.0, 156.2, FTIR (KBr, cm 1 ): 3178, 3323, 1600, 1518, MS (EI): m/z 171 (M + ). 3-Methoxy-5-phenylpyridine [6, , Ref. 6] N OMe 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.90 (s, 3H), (m, 6H), 8.27 (s, 1H), 8.44 (s, 1H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 55.6, 119.1, 127.1, 128.1, 128.9, 135.6, 137.4, 140.3, FTIR (KBr, cm 1 ): 1413, 1498, 1587, 2929, MS (EI): m/z 185 (M + ). 4-Hydroxybiphenyl [7, , Ref. 7] 1 H NMR (300 MHz, CDCl 3, TMS): δ 4.51 (br s, 1H), 6.89 (d, 2H, J = HO 8.5 Hz), (m, 7H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 115.5, 126.6, 128.2, 128.6, 133.7, 140.6, FTIR (KBr, cm 1 ): 1487, 1597, 3037, MS (EI): m/z 170 (M + ).
9 2-(Trifluromethyl)biphenyl [8, , Ref. 8] CF 3 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 8H), 7.70 (d, 1H, J = 7.7 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 122.7, (q), 126.4, 127.5, 127.6, 127.9, 128.0, 128.6, 129.3, 131.6, 132.4, 140.2, FTIR (KBr, cm 1 ): 1315, 1483, 1600, MS (EI): m/z 222 (M + ). 2-Hydroxybiphenyl [9, , Ref. 9] 1 H NMR (300 MHz, CDCl 3, TMS): δ 5.23 (bs, 1H), 6.94 (t, 2H), 7.20 (t, 2H), (m, 5H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 115.7, 120.7, , 128.0, 129.0, 129.1, 130.1, 136.9, FTIR (KBr, cm 1 ): 1101, 1327, 1481, 1585, 3028, MS (EI): m/z 170 (M + ). 2-Aminobiphenyl [10, , Ref. 10] NH 2 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.74 (bs, 2H), 6.81(d, 1H, J = 7.7 Hz), 6.88 (t, 1H), 7.21(m, 2H), 7.41 (m, 1H), 7.49 (m, 4H), 13 C NMR (75 MHz, CDCl 3, TMS): δ 115.5, 118.5, 127.0, 127.5, 128.3, 128.6, 128.9, 130.3, 139.3, FTIR (KBr, cm 1 ): 1292, 1481, 1612, 3022, 3387, MS (EI): m/z 169 (M + ). 2-Methoxybiphenyl [11, , Ref. 11] OMe 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.77 (s, 3H), (m, 2H), (m, 3H), 7.34 (t, 2H), 7.51 (d, 2H, J = 6.8 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 55.5, 111.0, 120.7, 126.8, 127.8, 128.5, 129.4, 130.5, 130.7, 138.3, FTIR (KBr, cm 1 ): 1247, 1467, MS (EI): m/z 184 (M + ).
![9] 1 H NMR (300 MHz, CDCl 3, TMS): δ 5.23 (bs, 1H), 6.94 (t, 2H), 7.20 (t, 2H), 7.33 7.41 (m, 5H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 115.7, 120.7, 127.71, 128.](/docs-images/50/20254583/images/page_9.jpg "0, 129.0, 129.1, 130.1, 136.9, 152.8. FTIR (KBr, cm 1 ): 1101, 1327, 1481, 1585, 3028, 3535 3558. MS (EI): m/z 170 (M + ). 2-Aminobiphenyl [10, 90-41-5, Ref.")
10 4-Methoxy-[3-(hydroxymethyl)phenyl]benzene [12, , Ref. 12] 1 H NMR (300 MHz, CDCl 3, TMS): δ 1.79 (s, 1H), 3.83 (s, 3H), MeO 4.72 (s, 2H), 6.93 (d, 2H, 8.8 Hz), 7.26 (d, 1H, J = 7.4 Hz), 7.38 (t, 1H, J = 7.7 Hz), (m, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 55.3, 65.4, 114.1, 125.2, 125.2, 125.9, 128.0, 128.8, 133.3, 141.0, 141.2, FTIR (KBr, cm 1 ): 3254, 1604, 1516, 1251, MS (EI): m/z 214 (M + ). 4-Methoxybiphenyl [13, , Ref. 13] MeO 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.82 (s, 3H), 6.93 (d, 2H, J = 8.5 Hz), 7.27 (t, 1H), 7.38 (t, 2H), 7.51 (t, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 55.3, 114.1, 126.6, 128.0, 128.6, 133.6, 140.6, FTIR (KBr, cm 1 ): 1037, 1247, 1485, MS (EI): m/z 184 (M + ). 4-Methylbiphenyl [14, , Ref. 13] 1 H NMR (300 MHz, CDCl 3, TMS): δ 2.37 (s, 3H), 7.20 (d, 2H, J = Me 7.7 Hz), 7.28 (t, 1H), 7.38 (t, 2H), 7.45 (d, 2H, J = 7.9 Hz), 7.54 (d, 2H, J = 7.4 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 21.2, 126.9, 128.6, 129.3, 136.8, 138.2, FTIR (KBr, cm 1 ): 1485, MS (EI): m/z 168 (M + ). 4-Methyl-[3-(hydroxymethyl)phenyl]benzene [15, , Ref. 14] Me 1 H NMR (300 MHz, CDCl 3, TMS): δ 1.95 (s, 1H), 2.37 (s, 3H), 4.70 (s, 2H), 7.20 (d, 2H, 7.7 Hz), 7.27 (d, 1H, J = 7.7 Hz), 7.37 (t, 1H, J = 7.4 Hz), 7.45 (d, 3H, J = 7.7 Hz) 7.54 (s, 1H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 21.2,
![MS (EI): m/z 214 (M + ). 4-Methoxybiphenyl [13, 613-37-6, Ref. 13] MeO 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.82 (s, 3H), 6.93 (d, 2H, J = 8.5 Hz), 7.27 (t, 1H), 7.38 (t, 2H), 7.51 (t, 4H).](/docs-images/50/20254583/images/page_10.jpg "13 C NMR (75 MHz, CDCl 3, TMS): δ 55.3, 114.1, 126.6, 128.0, 128.6, 133.6, 140.6, 158.9. FTIR (KBr, cm 1 ): 1037, 1247, 1485, 1604. MS (EI): m/z 184 (M + ). 4-Methylbiphenyl [14, 644-08-06, Ref.")
11 65.3, 125.5, 126.1, 126.8, 128.8, 129.4, 137.0, 137.9, 141.1, FTIR (KBr, cm 1 ): 3375, 3302, 2916, 1608, 1485, 1342, MS (EI): m/z 198 (M + ). 4-Nitro-[3-(hydroxymethyl)phenyl]benzene [16, , Ref. 6] 1 H NMR (300 MHz, CDCl 3, TMS): δ 2.05 (s, 1H), 4.78 (s, 2H), O 2 N (m, 4H), 7.61 (s, 1H), 7.70 (d, 2H, J = 8.5 Hz), 8.25 (d, 2H, J = 8.5 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 64.9, 123.9, 125.7, 126.4, 127.2, 127.7, 129.2, 138.8, 141.7, 146.8, FTIR (KBr, cm 1 ): 1035, 1346, 1516, 1597, 2929, MS (EI): m/z 229 (M + ). 4-Nitrobiphenyl [17, , Ref. 13] O 2 N 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 3H), 7.60 (d, 2H, J = 6.8 Hz), 7.71 (d, 2H, J = 8.8 Hz), 8.27 (d, 2H, 8.8 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 124.0, 127.2, 127.7, 128.8, 129.0, 138.6, 146.9, FTIR (KBr, cm 1 ): 1109, 1348, 1512, 1595, MS (EI): m/z 199 (M + ). 4-Chloro-[3-(hydroxymethyl)phenyl]benzene [18, , Ref. 6] Cl 1 H NMR (300 MHz, CDCl 3, TMS): δ 1.93 (s, 1H), 4.72 (s, 2H), 7.35 (m, 4H), 7.47 (m, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 65.2, 125.4, 126.0, 126.1, 128.2, 128.8, 129.0, 133.3, 139.2, 140.1, FTIR (KBr, cm 1 ): 3348, 1475, 1433, 1338, MS (EI): m/z 218 (M + ).
12 4-Chlorobiphenyl [19, , Ref. 15] Cl 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 9H), 13 C NMR (75 MHz, CDCl 3, TMS): δ 126.8, 127.4, 128.2, 128.7, 133.2, 139.4, FTIR (KBr, cm 1 ): 1099, 1479, 1591, MS (EI): m/z 188 (M + ). 4-Phenylbenzaldehyde [20, , Ref. 1] 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 3H), 7.59 (d, 2H, C J = 7.7 Hz), 7.71 (d, 2H, J = 7.9 Hz), 7.91 (d, 2H, 8.2 Hz), (s, 1H), 13 C NMR (75 MHz, CDCl 3, TMS): δ 127.2, 127.5, 128.3, 128.8, 130.1, 135.0, 139.5, 147.0, FTIR (KBr, cm -1 ): 1217, 1481, 1602, 1689, 2746, 2835, MS (EI): m/z 182 (M + ). 4-Acetylbiphenyl [21, , Ref. 15] Ac 1 H NMR (300 MHz, CDCl 3, TMS): δ 2.63 (s, 3H), (m, 3H), 7.59 (d, 2H, J = 7.1 Hz), 7.66 (d, 2H, J = 7.9 Hz), 8.01 (d, 2H, J = 8.25 Hz). 13 C NMR (75 MHz, CDCl 3, TMS): δ 26.8, 127.1, 128.1, 128.8, 135.7, 139.7, 145.6, FTIR (KBr, cm 1 ): 2999, 1678, 1600, 1558, MS (EI): m/z 196 (M + ). 1,2-Diphenylbenzene [22, , Ref. 16] 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 10H), 7.46 (s, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 126.3, 127.0, , 127.3, 127.7, MS (EI): m/z 230 (M + ) , 129.8, 130.5, 140.4, FTIR (KBr, cm 1 ): 1265, 1421, 1618, 2924.
13 1,2-bis[(3-hydroxymethyl)phenyl]benzene [23, New compound] 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.24 (s, 2H), 4.40 (s, 4H), (m, 8H), (m, 4H), 13 C NMR (75 MHz, CDCl 3, TMS): δ 64.7, 125.2, 127.4, 127.9, 128.8, 130.1, 140.1, FTIR (KBr, cm 1 ): 1045, 1406, 1460, 1624, MS (EI): m/z 290 (M + ). Anal. Calcd for C 20 H 18 O 2 : C, 82.73; H, 6.25; O, Found: C, 82.71; H, ,4-Diphenylbenzene [24, , Ref. 17] 1 H NMR (300 MHz, CDCl 3, TMS): δ 7.36 (t, 2H, J = 7.1 Hz), 7.45 (t, 4H, J = 7.5 Hz), 7.62 (d, 4H, J = 7.1 Hz), 7.65 (s, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 126.9, 127.2, 127.4, 128.7, 140.0, FTIR (KBr, cm 1 ): 3034, 1604, MS (EI): m/z 230 (M + ). 1,4-Bis[3-(hydroxymethyl)phenyl]benzene [25, New compound] HO 1 H NMR (300 MHz, CDCl 3, TMS): δ 4.57 (d, 4H), 5.28 (t, 2H), 7.32 (d, J = 7.42 Hz, 2H), 7.43 (t, J = 7.70 Hz, 2H), 7.58 (d, J = 7.70 Hz, 2H), 7.67 (s, 2H), 7.76 (s, 4H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 62.9, 124.6, 125.6, 127.1, 128.7, 139.2, 139.3, FTIR (KBr, cm 1 ): 1008, 1201, 1433, 1481, 1604, 2929, MS (DI): m/z 290 (M + ). Anal. Calcd for C 20 H 18 O 2 : C, 82.73; H, 6.25; O, Found: C, 82.52; H, 6.10.
![71; H, 6.28. 1,4-Diphenylbenzene [24, 92-94-4, Ref. 17] 1 H NMR (300 MHz, CDCl 3, TMS): δ 7.36 (t, 2H, J = 7.1 Hz), 7.45 (t, 4H, J = 7.5 Hz), 7.62 (d, 4H, J = 7.1 Hz), 7.65 (s, 4H).](/docs-images/50/20254583/images/page_13.jpg "13 C NMR (75 MHz, CDCl 3, TMS): δ 126.9, 127.2, 127.4, 128.7, 140.0, 140.5. FTIR (KBr, cm 1 ): 3034, 1604, 1479. MS (EI): m/z 230 (M + ).")
14 1,3-Diphenylbenzene [26, , Ref. 17] 1 H NMR (300 MHz, CDCl 3, TMS): δ (m, 13H), 7.79 (s, 3H), 13 C NMR (75 MHz, CDCl 3, TMS): δ 126.0, 127.1, 127.3, 128.7, 129.0, (EI): m/z 230 (M + ) , FTIR (KBr, cm 1 ):3057, 3032, 1597, 1568, 1496, MS 1,3-Bis[3-(hydroxymethyl)phenyl]benzene [27, New compound] 1 H NMR (300 MHz, CDCl 3, TMS): δ 3.21 (s, 2H), 4.58 (s, 4H), HO 7.19 (d, J = 7.1 Hz, 2H), (m, 7H), 7.50 (s, 2H), 7.67 (s, 1H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 64.8, 125.4, 125.5, 125.7, 125.8, 125.9, 126.0, 126.1, 128.7, 129.0, 141.0, 141.2, FTIR (KBr, cm 1 ): 1028, 1265, 1417, 1602, 2926, MS (DI): m/z 290 (M + ). Anal. Calcd for C 20 H 18 O 2 : C, 82.73; H, 6.25; O, Found: C, 82.64; H, ,3,5-Triphenylbenzene [28, , Ref. 16] 1 H NMR (300 MHz, CDCl 3, TMS): δ 7.37 (t, 3H, J = 7.1 Hz), 7.46 (t, 5H, J = 7.7 Hz), 7.68 (d, 5H, J = 7.45 Hz), 7.77 (s, 3H). 13 C NMR (75 MHz, CDCl 3, TMS): δ 125.1, 127.2, 127.4, 128.4, 141.0, FTIR (KBr, cm 1 ): 3057, 3033, 1593, 1494, MS (EI): m/z 306 (M + ).
15 1,3,5-Tris[3-(hydroxymethyl)phenyl]benzene [29, New compound] HO 1 H NMR (300 MHz, DMSO-d 6, TMS): δ 4.61 (d, 6H, J = 5.7 Hz), 5.30 (t, 3H, J = 5.7 Hz), 7.36 (d, 3H, J = 7.4 Hz), 7.46 (t, 3H, J = 7.4 Hz), 7.70 (d, 3H, J = 7.4 Hz) 7.76 (s, 3H), 7.85 (s, 3H). 13 C NMR (75 MHz, DMSO-d 6, TMS): δ 62.9, 124.1, 125.0, 125.3, 125.8, 128.6, 139.7, 141.6, FTIR (KBr, cm 1 ): 3281, 2870, 1595, 1585, MS (DI): m/z 396 (M + ). Anal. Calcd for C 27 H 24 O 3 : C, 81.79; H, 6.10; O, Found: C, 81.77; H, 6.18.
16 7. References [1] J. Mao, J. Guo, F. Fang, S. J. Ji, Tetrahedron 2008, 64, [2] G. S. Hammond, C. E. Reeder, J. Am. Chem. Soc. 1958, 80, [3] D. P. Curran, A. I. Keller, J. Am. Chem. Soc. 2006, 128, [4] B. Tao, D. W. Boykin, J. Org. Chem. 2004, 69, [5] S. Zhu, S. Shi, S. W. Gerritz, M. J. Sofia, J. Comb. Chem. 2003, 5, [6] S. B. Waghmode, S. R. Borhade, Ind. J. Chem. 2010, 49B, [7] Y. Endo, K. Shudo, T. Okamoto, J. Am. Chem. Soc., 1982, 104, [8] D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, [9] Q. J. Zhou, K. Worm, R. E. Dolle, J. Org. Chem. 2004, 69, [10] L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 2005, 70, [11] M. E. Mowery, P. DeShong, J. Org. Chem. 1999, 64, [12] U. Grether, H. Waldmann, Chem. Eur. J. 2001, 7, [13] B. Tao, D. W. Boykin, J. Org. Chem. 2004, 69, [14] Y. Hatanaka, K. Goda, Y. Okahara, T. Hiyama, Tetrahedron 1994, 50, [15] Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, [16] S. Paul, J. H. Clark, Green Chem. 2003, 5, [17] D. J. Sinclair, M. S. Sherburn, J. Org. Chem. 2005, 70,
![[7] Y. Endo, K. Shudo, T. Okamoto, J. Am. Chem. Soc., 1982, 104, 6393-6397. [8] D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170-7173. [9] Q. J. Zhou, K. Worm, R.](/docs-images/50/20254583/images/page_16.jpg "E. Dolle, J. Org. Chem. 2004, 69, 5147-5149. [10] L. Liu, Y. Zhang, Y. Wang, J. Org. Chem. 2005, 70, 6122-6125. [11] M. E. Mowery, P. DeShong, J. Org. Chem. 1999, 64, 3266-3270. [12] U. Grether, H.")
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Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
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