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7 An organomanganate and an organozincate have been used in the iron-catalyzed cross-coupling of aryl electrophiles; see ref. 2h.
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11
Typical Experimental Procedure A (Table 2); 5-Phenyl-1-(trimethylsilyl)pent-1-yne: In a dry reaction vessel, a mixture of ZnCl2·TMEDA (379 mg, 1.5 mmol) and PhMgBr (0.93 M solution in THF, 3.22 mL, 3.0 mmol) was stirred for 1 h. To the resulting suspension was added 5-iodo-1-(trimethylsilyl)pent-1-yne (266 mg, 1.0 mmol), and then FeCl3 (0.1 M solution in THF, 0.5 mL, 0.05 mmol) at 0 °C. The reaction mixture was stirred at 50 °C for 0.5 h. After quenching with a saturated aqueous solution of NH4Cl, the mixture was filtered through a pad of Florisil®, and concentrated in vacuo. Purification by silica gel chromatography afforded 5-phenyl-1-(trimethylsilyl)pent-1-yne (201 mg, 93%); FTIR (neat): 2958 (w), 2902 (w), 2175 (w), 1478 (w), 1451 (s), 1395 (w), 1366 (s), 1268 (w), 1167 (w), 997 (s) cm-1; 1H NMR (500 MHz, CDCl3): δ = 7.31-7.25 (m, 3 H), 7.21-7.17 (m, 2 H), 2.72 (t, J = 7.6 Hz, 2 H), 2.24 (t, J = 7.1 Hz, 2 H), 1.84 (tt, J = 7.6, 7.1 Hz, 2 H), 0.16 (s, 9 H); 13C NMR (125 MHz, CDCl3): δ = 141.3, 128.2 (2 C), 128.0 (2 C), 125.5, 106.8, 87.4, 34.5, 30.0, 19.1, 0.0 (3 C); HRMS (EI, 70 eV): m/z calcd for C14H20Si [M]+, 216.1334; found, 216.1305; Anal. Calcd for C14H20Si: C, 77.71; H, 9.32. Found: C, 77.53; H, 9.13.
12
Typical Experimental Procedure B (Table 3); 4-(4-Cyanophenyl)-
N
-(benzyloxycarbonyl)piperidine: In a dry reaction vessel, a mixture of ArZnBr (0.48 M solution in THF, 4.2 mL, 2.0 mmol) and Me3SiCH2MgCl (1.1 M solution in Et2O, 1.8 mL, 2.0 mmol) was stirred at 0 °C for 1 h. To the resulting solution was added TMEDA (0.30 mL, 2.0 mmol), 4-bromo-N-(benzyloxycarbonyl)piperidine (298 mg, 1.0 mmol), and then FeCl3 (0.1 M solution in THF, 0.5 mL, 0.05 mmol) at 0 °C. The reaction mixture was stirred at 30 °C for 6 h. After quenching with a saturated aqueous solution of NH4Cl, the mixture was filtered through a pad of Florisil®, and concentrated in vacuo. Purification by silica gel chromatography afforded 4-(4-cyanophenyl)-N-(benzyloxycarbonyl)piperidine (253 mg, 79%); FTIR (neat): 3014 (w), 2943 (w), 2923 (w), 2856 (w), 2227 (m), 1688 (s), 1466 (m), 1455 (m), 1436 (m), 1273 (w), 1218 (s), 1125 (m), 1057 (m), 1009 (m), 917 (w), 838 (m), 760 (s), 702 (s) cm-1; 1H NMR (500 MHz, CDCl3): δ = 7.59 (d, J = 8.6 Hz, 2 H), 7.39-7.26 (m, 7 H), 5.16 (br s, 2 H), 4.35 (br s, 2 H), 2.89 (br s, 2 H), 1.90-1.78 (m, 2 H), 1.70-1.58 (m, 2 H); 13C NMR (125 MHz, CDCl3): δ = 155.2, 150.8, 136.7, 132.4 (2 C), 128.5 (2 C), 128.0, 127.9 (2 C), 127.6 (2 C), 118.8, 110.3, 67.2, 44.3 (2 C), 42.7, 32.6 (2 C); Anal. Calcd for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 74.80; H, 6.42; N, 8.54.
13
Wakabayashi K.
Yorimitsu H.
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