and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
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- Ιάνθη Βηθεσδά Θεοδοσίου
- 6 χρόνια πριν
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1 FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu Xiang, Ruiting Liu, and Xigeng Zhou* Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai , People s Republic of China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai , People s Republic of China xgzhou@fudan.edu.cn; Tel: (+86) Supporting Information Contents General methods.. S2 Characterization data... S5 References S10 Copies of NMR Spectra for 3a-3o, 5q and 5q...S11 X-ray Structure of 3b and 5q... S30 S1
2 General Methods Unless otherwise noted, all manipulations were performed in air. All iron salts (Purity: 99.0%) were purchased from commercial sources (Aladdin Reagents Company) and used without further purification. NMR spectra were recorded at 400 MHz for 1 H NMR, 100 MHz for 13 C NMR using CDCl 3 as solvent with TMS as the internal standard. MS and HRMS determinations were carried out in EI mode. All reactions were monitored by TLC. Flash column chromatography was carried out using mesh silica gel. Typical Procedure for the Disproportionation of Allylic Alcohols Using FeCl 3 6H 2 O as Catalyst To a toluene (1 ml) of allylic alcohol 1a (105 mg, 0.5 mmol) was added 5 mol % FeCl 3 6H 2 O (7 mg, mmol) and then the mixture was stirred at 80 o C. After completion of the reaction, the solvent was removed under reduced pressure. The residue was purified by a flash chromatography using petroleum ether/ethyl acetate as the eluent (V/V: 100/1). Typical Procedure for the Allylic Reduction of Allylic Alcohols 1a with Benzyl Alcohol Using FeCl 3 6H 2 O as Catalyst To a mixture of allylic alcohol 1a (105 mg, 0.5 mmol) and benzyl alcohol (0.2 ml, 2.0 mmol) in toluene (1 ml) was added 5 mol % FeCl 3 6H 2 O (7 mg, mmol) and the reaction mixture was stirred at 80 o C. After completion of the reaction, the mixture was quenched with saturated NH 4 Cl solution and the aqueous layer was extracted with ethyl acetate (3 10 ml). The combined organic layer was dried over Na 2 SO 4. After filtration and removal of solvent in vacuum, the crude product was purified with flash chromatography using petroleum ether/ethyl acetate as the eluent (V/V: 100/1). General Procedure for the Allylic Reduction of Allylic Derivatives with Benzyl Alcohol Using FeCl 3 6H 2 O as Catalyst S2
3 To a mixture of allylic derivatives 2 (0.5 mmol) and benzyl alcohol (2.0 mmol) in toluene (1 ml) was added 5 mol % FeCl 3 6H 2 O (7 mg, mmol) and then the reaction mixture was stirred at 80 o C. After completion of the reaction, the mixture was quenched with saturated NH 4 Cl solution and the aqueous layer was extracted with ethyl acetate (3 10 ml). The combined organic layer was dried over Na 2 SO 4. After filtration and removal of solvents under reduced pressure, the crude product was purified with flash chromatography. The Procedure for the Allylic Reduction of 1,3-Diphenylprop-2-en-1-ol-d with Benzyl Alcohol-d Using Anhydrous FeCl 3 as Catalyst. To a mixture of 1,3-diphenylprop-2-en-1-ol-d (105.5 mg, 0.5 mmol) and benzyl alcohol-d (0.5 ml) under argon atmosphere was added 5 mol % anhydrous FeCl 3 (4 mg, mmol) and then the reaction mixture was stirred at 80 o C. After completion of the reaction, the mixture was quenched with saturated NH 4 Cl solution and the aqueous layer was extracted with ethyl acetate (3 10 ml). The organic layers were combined and dried over Na 2 SO 4. After filtration and removal of solvent under reduced pressure, the crude product was purified with flash chromatography. The reduction product 3a was obtained in 92% yield. The Procedure for the Allylic Reduction of 1,3-Diphenylprop-2-en-1-ol with α,α-dideuteriobenzyl Alcohol Using Anhydrous FeCl 3 as Catalyst. To a mixture of 1,3-diphenylprop-2-en-1-ol (105 mg, 0.5 mmol) and α,α-dideuteriobenzyl alcohol (220 mg, 2.0 mmol) in toluene (1 ml) was added 5 mol % anhydrous FeCl 3 (4 mg, mmol) and then the reaction mixture was stirred at 80 o C. After completion of the reaction, the mixture was quenched with saturated NH 4 Cl solution and the aqueous layer was extracted with ethyl acetate (3 10 ml). The organic layers were combined and dried over Na 2 SO 4. After filtration and removal of solvent under reduced pressure, the crude product was purified with flash chromatography. The reduction product 3a was obtained in 90% yield. S3
4 The procedure for the reduction of 5q (5q') using anhydrous FeCl 3 as catalyst. To allylic benzyl ether 5q (0.3 mmol) in toluene (1.0 ml) was added 5 mol % anhydrous FeCl 3 (2.5 mg, mmol) and then the reaction mixture was stirred at 80 o C. After completion of the reaction, the mixture was quenched with saturated NH 4 Cl solution and the aqueous layer was extracted with ethyl acetate (3 10 ml). The combined organic layer was dried over Na 2 SO 4. After filtration and removal of solvent under reduced pressure, the crude product was purified with flash chromatography. The reduction products 3q and 3 q' were obtained. S4
5 Characterization Data 3a 1 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 6.41 (d, J = Hz, 1H), (m, 1H), 3.50 (d, J = 6.40 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.4, 137.7, 131.3, 129.5, 128.9, 128.8, 127.4, 126.5, 126.4, MS (EI) m/z: 194 (100) [M + ], 179 (43), 115 (49), 91 (16). 3a 2 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 6.45 (d, J = Hz, 1H), (m, 1H), 3.52 (d, J = 6.88 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.3, 137.6, 131.2, 129.3, 128.8, 128.6, 127.3, 126.3, 126.3, 39.2 (t, J = Hz, CHD). MS (EI) m/z: 195 (100) [M + ], 179 (42), 116 (48), 92 (14). 3b 3 1 H NMR (400 MHz, CDCl 3 ) δ (d, J = 8.24 Hz, 2H), (m, 6H), 6.38 (d, J = Hz, 1H), (m, 1H), 3.46 (d, J = 6.88 Hz, 2H), 2.30 (s, 3H), 2.29 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 137.4, 136.9, 135.8, 135.0, 130.9, 129.4, 129.4, 128.8, 128.7, 126.2, 39.1, 21.3, MS (EI) m/z: 222 (84) [M + ], 207 (100), 192 (27), 129 (40), 115 (50). 3c 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 7H), 6.57 (d, J = Hz, 1H), (m, 1H), 3.53 (d, J = 6.88 Hz, 2H), 2.33 (s, 3H), 2.28 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 138.5, 136.9, 136.5, 135.2, 130.4, 130.3, 130.0, 129.3, 129.1, 127.2, 126.5, 126.3, 126.2, 125.7, 37.4, 20.0, MS (EI) m/z: 222 (100) S5
6 [M + ], 207 (82), 192 (29), 129 (52), 115 (67), 104 (70). HRMS (EI) calcd for C 17 H 18 : , found: d 4 1 H NMR (400 MHz, CDCl 3 ) δ (m, 4H), (m, 4H), 6.37 (d, J = Hz, 1H), (m, 1H), 3.79 (s, 6H), 3.46 (d, J = 6.88 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.9, 158.1, 132.6, 130.4, 130.2, 129.7, 128.5, 127.6, 127.3, 114.0, 55.4, MS (EI) m/z: 254 (100) [M + ], 239 (15), 223 (48), 145 (27), 115 (22). 3e 5 1 H NMR (400 MHz, CDCl 3 ) δ (m, 6H), 7.14 (d, J = 8.24 Hz, 2H), 6.36 (d, J = Hz, 1H), (m, 1H), 3.48 (d, J = 6.40 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 138.3, 135.8, 132.9, 132.2, 130.3, 130.1, 129.4, 128.8, 128.7, 127.4, MS (EI) m/z: 262 (50) [M + ], 227 (100), 192 (65), 149 (43), 115 (72). HRMS (EI) calcd for C 15 H 12 Cl 2 : , found: f/3f 1,3 1 H NMR (400 MHz, CDCl 3 ) δ (m, 9H), (m, 2H), 3.50 (d, J = 5.96 Hz, 1.1H), 3.46 (d, J = 5.96 Hz, 0.9H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.0, 138.7, 137.4, 136.1, 132.8, 132.1, 131.6, 130.2, 130.0, 128.8, 128.8, 128.7, 127.5, 127.4, 126.5, 126.3, 39.5, MS (EI) m/z: 228 (78) [M + ], 193 (100), 178 (43), 115 (90). 3g/3g 3,6 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), 3.48 (d, J = 5.96 Hz, 2H), 2.32 (s, 2H), 2.31 (s, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 138.9, 137.2, 136.9, 136.1, 135.9, 134.6, 132.7, 132.0, 131.4, 130.4, 130.1, 129.7, 129.3, 128.7, S6
7 128.7, 127.6, 127.4, 126.2, 39.0, 38.7, 21.3, MS (EI) m/z: 242 (100) [M + ], 227 (60), 207 (63), 192 (57), 115 (70). 3h/3h 1,6 1 H NMR (400 MHz, CDCl 3 ) δ (m, 9H), (m, 2H), 3.49 (d, J = 6.88 Hz, 0.7H), 3.47 (d, J = 6.88 Hz, 1.3H), 2.30 (s, 2H), 2.28 (s, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.6, 137.7, 137.3, 137.0, 135.9, 134.9, 131.1, 131.1, 129.7, 129.4, 128.9, 128.8, 128.7, 128.4, 127.3, 126.3, 126.3, 39.6, 39.2, 21.4, MS (EI) m/z: 208 (100) [M + ], 193 (95), 178 (30), 115 (74), 91 (36). 3i/3i 1 1 H NMR (400 MHz, CDCl 3 ) δ (m, 9H), 6.64 (d, J = Hz, 0.5H), (m, 1.5H), 3.54 (d, J = 6.88 Hz, 1H), 3.48 (d, J = 5.04 Hz, 1H), 2.31 (s, 1.5H), 2.30 (s, 1.5H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.5, 138.5, 137.8, 136.8, 136.6, 135.3, 131.1, 130.7, 130.5, 130.4,, 129.5, 129.2, 128.9, 128.7, 127.3, 126.6, 126.4, 126.4, 126.3, 125.8, 39.9, 37.1, 20.1, MS (EI) m/z: 208 (100) [M + ], 193 (80), 178 (34), 115 (76). 3j/3j 1,7 1 H NMR (400 MHz, CDCl 3 ) δ (m, 7H), 6.84 (d, J = 8.68 Hz, 2H), (m, 2H), 3.76 (s, 3H), 3.50 (d, J = 6.88 Hz, 0.3H), 3.46 (d, J = 6.44 Hz, 1.7H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.2, 132.3, 130.8, 129.8, 129.8, 128.8, 128.6, 127.4, 127.2, 126.2, 114.0, 55.4, MS (EI) m/z: 224 (100) [M + ], 209 (18), 193 (31), 178 (16), 115 (44). 3k 8 1 H NMR (400 MHz, CDCl 3 ) δ (m, 7H), (m, 2H), 6.43 (d, J = S7
8 16.04 Hz, 1H), (m, 1H), 3.84 (s, 3H), 3.53 (d, J =5.96 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 137.7, 130.6, 129.8, 128.9, 128.6, 128.4, 127.4, 126.8, 126.0, 120.5, 110.3, 55.4, MS (EI) m/z: 224 (100) [M + ], 209 (26), 193 (50), 115 (46), 91 (38). 3l/3l 1 1 H NMR (400 MHz, CDCl 3 ) δ (m, 7H), (m, 2H), (m, 2), 3.49 (d, J = 6.88 Hz, 1.1H), 3.46 (d, J = 6.40 Hz, 0.9H). 13 C NMR (100 MHz, CDCl 3 ) δ 163.2, 162.7, 160.7, 160.2, 140.0, 137.3, 135.7, 135.7, 133.6, 133.5, 131.2, 130.0, 129.9, 129.8, 129.0, 128.9, 128.9, 128.6, 128.5, 128.5, 127.5, 127.4, 127.2, 126.2, 126.1, 115.4, 115.3, 115.2, 115.1, 39.2, MS (EI) m/z: 212 (40) [M + ], 193 (20), 105 (100), 91 (50). 3m/3m 1 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 7H), (m, 2H), (m, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 140.9, 139.5, 137.1, 132.1, 131.9, 129.7, 129.0, 128.9, 128.7, 128.6, 128.5, 128.5, 128.4, 128.3, 127.8, 127.3, 126.3, 126.2, 126.1, 125.7, 125.6, 125.5, 125.4, 125.4, 125.4, 125.3, 123.0, 122.9, 39.3, MS (EI) m/z: 262 (100) [M + ], 212 (84), 193 (61), 178 (26), 115 (63). 3n/3n 1 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 1H), (m, 6H), (m, 2H), 3.60 (d, J = 6.40 Hz, 0.5H), 3.55 (d, J = 5.52 Hz, 1.5H). 13 C NMR (100 MHz, CDCl 3 ) δ 148.6, 139.4, 139.3, 135.1, 132.9, 132.6, 132.1, 129.5, 128.9, 128.9, 128.8, 128.7, 128.5, 127.7, 126.6, 126.4, 123.6, 121.8, 121.5, 120.8, 39.4, MS (EI) m/z: 239 (81) [M + ], 222 (70), 192 (100), 178 (28), 115 (51). S8
9 3o/3o 4 1 H NMR (400 MHz, CDCl 3 ) δ 8.12 (d, J = 8.24 Hz, 2H), (m, 7H), (m, 2H), 3.63 (d, J = 6.40 Hz, 0.3H), 3.59 (d, J = 6.40 Hz, 1.7H). 13 C NMR (100 MHz, CDCl 3 ) δ 146.7, 144.1, 139.1, 134.7, 129.5, 128.8, 126.7, 126.6, 126.3, 124.1, 123.9, MS (EI) m/z: 239 (100) [M + ], 222 (37), 192 (80), 178 (44), 115 (70). 3p/3p 1 H NMR (400 MHz, CDCl 3 ) δ 8.11 (d, J = 8.72 Hz, 2H), 7.42 (d, J = 8.72 Hz, 2H), 7.14 (d, J = 8.68 Hz, 2H), 6.86 (d, J = 8.68 Hz, 2H), (m, 1H), 6.44 (d, J = Hz, 1H), 3.78 (s, 3H), 3.52 (d, J = 6.44 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.4, 146.6, 144.1, 135.2, 131.1, 129.8, 128.9, 126.6, 124.0, 114.2, 55.4, MS (EI) m/z: 269 (100) [M + ], 238 (12), 222 (29), 192 (20), 178 (32), 121 (41). HRMS (EI) calcd for C 16 H 15 NO 3 : , found: q/3q 1 H NMR (400 MHz, CDCl 3 ) δ 8.14 (d, J = 8.72 Hz, 2H), 7.45 (d, J = 8.72 Hz, 2H), (m, 4H), (m, 2H), 3.55 (d, J = 6.40 Hz, 2H), 2.34 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 146.6, 144.1, 136.2,136.0, 135.0, 129.4, 129.0, 128.7, 126.6, 124.1, 39.1, MS (EI) m/z: 253 (100) [M + ], 238 (48), 222 (10), 192 (70), 115 (50), 105 (24). HRMS (EI) calcd for C 16 H 15 NO 2 : , found: q 1 H NMR (CDCl 3, 400 MHz) δ 8.20 (d, J = 9.16 Hz, 2H), 7.59 (d, J = 8.68 Hz, 2H), (m, 4H), 7.12 (d, J = 7.80 Hz, 2H), 6.64 (d, J = Hz, 1H), (dd, J = 7.80 Hz, Hz, 1H), 5.07 (d, J = 7.36 Hz, 1H), (dd, J = Hz, 2H), 2.32 (s, 3H). S9
10 5q 1 H NMR (CDCl 3, 400 MHz) δ 8.12 (d, J = 8.72 Hz, 2H), 7.45 (d, J = 8.68 Hz, 2H), (m, 5H), 7.20 (d, J = 8.24 Hz, 2H), 6.68 (d, J = Hz, 1H), (dd, J = 5.96 Hz, Hz, 1H), 5.02 (d, J = 5.96 Hz, 1H), (dd, J = Hz, 2H), 2.36 (s, 3H). References: 1. Tsukamoto, H.; Uchiyama, T.; Suzuki, T.; Kondo, Y. Org. Biomol. Chem. 2008, 6, Hayashi, T.; Ito, H.; Kumada, M. Tetrahedron Lett. 1982, 23, Dey, R.; Chattopadhyay, K.; Ranu, B. C. J. Org. Chem. 2008, 73, Shen, Y. C.; Yao, J. Z. J. Org. Chem. 1996, 61, Moreno-Maiias, M.; Pajuelo, F.; Pleixats, R. J. Org. Chem. 1995, 60, Narahashi, H.; Shimizu, I.; Yamamoto, A. J. Organomet. Chem. 2008, 693, Manabe, K.; Nakada, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2005, 347, Nishibayashi, Y.; Yamanashi, M.; Takagi, Y.; Hidai, M. Chem. Commun. 1997, 859. S10
11 Copies of NMR Spectra for 3a-3q, 5q and 5q` 3a (Table 3 entry 1) S11
12 3a (Scheme 3) S12
13 3b (Table 3, entry 2) S13
14 3c (Table 3, entry 3) S14
15 3d (Table 3, entry 4) S15
16 3e (Table 3, entry 5) S16
17 3f (Table 3, entry 6) S17
18 3g (Table 3, entry 7) S18
19 3h (Table 3, entry 8) S19
20 3i (Table 3, entry 9) S20
21 3j (Table 3, entry 10) 3k (Table 3, entry 11) S21
22 S22
23 3l (Table 3, entry 12) S23
24 3m (Table 3, entry 13) S24
25 3n (Table 3, entry 14) S25
26 3o (Table 3, entry 15) S26
27 3p (Table 3, entry 16) S27
28 3q (Table 3, entry 17) S28
29 5q (Scheme 3) 5q' (Scheme 3) S29
30 Figure 1. The Single-crystal X-ray Structure of 3b Figure 2. X-ray structure of 5q S30
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