Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2
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1 Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with β-nitroalkenes Jing Zheng, Dahai Wang, and Sunliang Cui* College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang , China Contents 1. General Information S2 2. Typical Synthesis Procedure of 3a S2-S3 3. Characterization of 3 and 6 S3-S27 4. Radical Scavenger Test S27-S28 5. Copies of NMR Spectra S29-S80 S1
2 1. General Information: Infrared spectra were obtained on a FTIR spectrometer. 1 H NMR and 13 C NMR spectra were recorded on BRUKER AVANCE III 500 or BRUKER AVANCE III 400 spectrometer. CDCl 3 were used as solvent. Chemical shifts were referenced relative to residual solvent. The following abbreviations are used to describe peak patterns where appropriate: br = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dq = double quartet. Coupling constants (J) are reported in Hertz (Hz). HRMS were performed on Waters GCT Premier Time of Flight Mass Spectrometer (EI). Melting points were measured with micro melting point apparatus. Fe(acac) 3, PhSiH 3, EtOH were commercial available, and nitroalkenes were prepared from aldehydes and nitromethane. The following alkenes were commercially available: 2-methyl-2-propen-1-ol (2c, and precursor of 2a), 3-Chloro-2-methylpropene (precursor of 2b), 3-methyl-3-buten-1-ol (2d), N-(tert-Butoxycarbonyl)-4-piperidone (precursor of 2e), 3,3-dimethylallylbromide (precursor of 2f), but-3-enenitrile (2g), 4-allylanisole (2h), allyltrimethylsilane (2i), cyclohexene (2j), 1-methyl-1-cyclohexene (2k), bicyclo[2.2.1]hept-2-ene (2l), (S)-(-)-β-Citronellol (2m), L-Menthol (precursor to 2n). 2. Typical Procedure for Synthesis of 3a: S2
3 1a NO 2 + OBn 2a (10 mol %) Fe(acac) 3 PhSiH 3 (2 equiv) EtOH, 60 o C 3a OBn A Schlenk tube containing β-nitrostyrene 1a (30 mg, 0.2 mmol), Fe(acac) 3 (7.2 mg, 10 mol %) were evacuated and purged with Argon three times. Afterwards, (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), PhSiH 3 (43.2 mg, 0.4 mmol) and 2 ml EtOH was added via syringe. The solution was kept at 60 o C for 8 h. Then the solution was diluted with CH 2 Cl 2 and transferred to a round bottom flask. Silica gel was added to the flask and volatiles were evaporated under vacuum. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent to give 3a as a pale yellow liquid (48mg, 90% yield). 3. Characterization of 3 and 6: (E)-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)benzene (3a) Prepared following the Typical Procedure in 90% yield as a pale yellow liquid (48 mg, mmol) for 3a, from β-nitrostyrene 1a (30 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. S3
4 Ph OBn 3a Pale yellow liquid; R f = 0.46 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 400MHz), δ: (m, 6H), (m, 3H), (m, 1H), 6.38 (d, J = 16.4 Hz, 1H), 6.29 (d, J = 16.4 Hz, 1H), 4.55 (s, 2H), 3.29 (s, 2H), 1.16 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 138.9, 138.1, 138.0, 128.6, 128.4, 127.6, 127.5, 127.0, 126.9, 126.3, 79.5, 73.4, 38.0, 24.8; IR (film) v: 3060, 3028, 2960, 2925, 2855, 1692, 1647, 1547, 1202, 1098, 1024, 739, 694 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 22 O (M + ): ; Found: (E)-(3,3-dimethyl-4-phenoxybut-1-en-1-yl)benzene (3b) Prepared following the Typical Procedure in 84% yield as a pale yellow liquid (42 mg, mmol) for 3b, from β-nitrostyrene 1a (30 mg, 0.2 mmol), ((2-methylallyl)oxy)benzene 2b (59.2 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using petroleum ether as eluent. Ph OPh 3b Pale yellow liquid; R f = 0.52 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 4H), (m, S4
5 1H), (m, 3H), 6.47 (d, J = 16.0 Hz, 1H), 6.37 (d, J = 16.0 Hz, 1H), 3.78 (s, 2H), 1.28 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 159.5, 137.8, 137.2, 129.5, 128.6, 127.5, 127.2, 126.3, 120.7, 114.8, 76.6, 37.7, 24.7; IR (film) v: 3065, 3031, 2959, 2924, 2858, 1595, 1530, 1496, 1296, 1077, 1043, 920, 881, 825 cm -1 ; HRMS (EI) (m/z): calcd for C 18 H 20 O (M + ): ; Found: (E)-2,2-dimethyl-4-phenylbut-3-en-1-ol (3c) Prepared following the Typical Procedure in 70% yield as a yellow liquid (24.6 mg, mmol) for 3c, from β-nitrostyrene 1a (30 mg, 0.2 mmol), 2-methyl-2-propen-1-ol 2c (28.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:10) as eluent. Yellow liquid; R f = 0.15 (EtOAc/Petroleum ether 1:10); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.42 (d, J = 16.4 Hz, 1H), 6.18 (d, J = 16.4 Hz, 1H), 3.43 (s, 2H), 1.14 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 137.4, 136.9, 128.8, 128.7, 127.4, 126.3, 71.8, 39.0, 24.0; IR (film) v: 3456, 3065, 2963, 2860, 1547, 1460, 1390, 1370, 1266, 1135, 1074, 971, 740, 701, 604 cm -1 ; HRMS (EI) (m/z): S5
6 calcd for C 12 H 16 O (M + ): ; Found: (E)-3,3-dimethyl-5-phenylpent-4-en-1-ol (3d) Prepared following the Typical Procedure in 67% yield as a yellow liquid (24 mg, mmol) for 3d, from β-nitrostyrene 1a (30 mg, 0.2 mmol), 3-methyl-3-buten-1-ol 2d (33.6 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:10) as eluent. Yellow liquid; R f = 0.15 (EtOAc/Petroleum ether 1:10); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.32 (d, J = 16.4 Hz, 1H), 6.23 (d, J = 16.4 Hz, 1H), 3.69 (t, J = 7.2 Hz, 2H), 1.72 (t, J = 7.2 Hz, 2H), 1.15 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 140.1, 137.7, 128.7, 127.2, , , 60.3, 45.7, 35.6, 27.7; IR (film) v: 3540, 3026, 2957, 2925, 2857, 1726, 1692, 1647, 1528, 1532, 1462, 1391, 1371, 1132, 972, 788 cm -1 ; HRMS (EI) (m/z): calcd for C 13 H 18 O (M + ): ; Found: tert-butyl (E)-4-methyl-4-styrylpiperidine-1-carboxylate (3e) Prepared following the Typical Procedure in 42% yield as a yellow S6
7 liquid (25 mg, mmol) for 3e, from β-nitrostyrene 1a (30 mg, 0.2 mmol), tert-butyl 4-methylenepiperidine-1-carboxylate 2e (78.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:20) as eluent. Ph N Boc 3e Pale yellow liquid; R f = 0.25 (EtOAc/Petroleum ether 1:20); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.35 (d, J = 16.4 Hz, 1H), 6.17 (d, J = 16.4 Hz, 1H), (m, 2H), (m, 2H), (m, 4H), 1.46 (s, 9H), 1.13(s, 3H); 13 C NMR (CDCl 3, 100MHz), δ: 155.1, 138.7, 137.7, 128.7, 127.4, 127.3, 126.1, 79.4, 37.0, 34.9, 29.8, 28.6, 27.0; IR (film) v: 2965, 2856, 2361, 1947, 1720, 1601, 1365, 1251, 1108, 1023, 969, 911 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 27 NO 2 (M + ): ; Found: (E)-(3,3-dimethyl-5-phenoxypent-1-en-1-yl)benzene (3f) Prepared following the Typical Procedure in 62% yield as a yellow liquid (33 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), ((3-methylbut-2-en-1-yl)oxy)benzene 2f (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at S7
8 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. Ph OPh 3f Pale yellow liquid; R f = 0.45 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 500MHz), δ: (m, 2H), (m, 2H), (m, 2H), (m, 1H), 6.92 (t, 1H), (m, 2H), 6.35 (d, J = 16.0 Hz, 1H), 6.25 (d, J = 16.0 Hz, 1H), 4.00 (t, J = 7.0 Hz, 2H), 1.94 (t, J = 7.0 Hz, 2H), 1.21 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 159.0, 139.7, 137.8, 129.5, 128.7, 127.1, 126.5, 126.2, 120.6, 114.6, 65.2, 41.8, 35.6, 27.8; IR (film) v: 3063, 3029, 2958, 2929, 2870, 1595, 1532, 1496, 1296, 1078, 1031, 783, 749, 691, 644 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 22 O (M + ): ; Found: (E)-3-methyl-5-phenylpent-4-enenitrile (3g) Prepared following the Typical Procedure in 56% yield as a pale yellow liquid (19 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), but-3-enenitrile 2g (26.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using petroleum ether as eluent. S8
9 Pale yellow liquid; R f = 0.36 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 500MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.49 (d, J = 16.0 Hz, 1H), 6.13 (dd, J 1 = 15.5 Hz, J 2 = 7.5 Hz, 1H), (m, 1H), (m, 2H), 1.29 (d, J = 7.0 Hz, 3H); 13 C NMR (CDCl 3, 100MHz), δ: 136.7, 131.6, 130.8, 128.7, 127.8, 126.5, 118.6, 34.2, 25.1, 19.9; IR (film) v: 3060, 3027, 2964, 2924, 2856, 1692, 1547, 1458, 1461, 1390, 1371, 1073, 791, 739 cm -1 ; HRMS (EI) (m/z): calcd for C 12 H 13 N (M + ): ; Found: (E)-1-methoxy-4-(2-methyl-4-phenylbut-3-en-1-yl)benzene (3h) Prepared following the Typical Procedure in 72% yield as a pale yellow liquid (36 mg, mmol) for 3h, from β-nitrostyrene 1a (30 mg, 0.2 mmol), 1-allyl-4-methoxybenzene 2h (59.2 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:50) as eluent. Pale yellow liquid; R f = 0.32 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 400MHz), δ: (m, 4H), (m, 1H), 7.10 (d, J = S9
10 8.4 Hz, 2H), 6.83 (d, J = 8.4 Hz, 2H), 6.32 (d, J = 16.0 Hz, 1H), 6.19 (dd, J 1 = 16.0 Hz, J 2 = 6.8 Hz, 1H), 3.80 (s, 3H), (m, 1H), (m, 2H), 1.09 (d, J = 6.4 Hz, 3H); 13 C NMR (CDCl 3, 100MHz), δ: 157.9, 138.0, 136.2, 132.7, 130.3, 128.6, 128.3, 127.0, 126.1, 113.7, 55.4, 42.8, 39.1, 19.9; IR (film) v: 3027, 2959, 2923, 2845, 1611, 1549, 1511, 1299, 1246, 1178, 1076, 907, 833, 747 cm -1 ; HRMS (EI) (m/z): calcd for C 18 H 20 O (M + ): ; Found: (E)-trimethyl(2-methyl-4-phenylbut-3-en-1-yl)silane (3i) Prepared following the Typical Procedure in 45% yield as a pale yellow liquid (19.6 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), allyltrimethylsilane 2i (45.6 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. Ph 3i TMS Pale yellow liquid; R f = 0.42 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.32 (d, J = 16.0 Hz, 1H), 6.12 (dd, J 1 = 16.0 Hz, J 2 = 8.0 Hz, 1H), (m, 1H), 1.12 (d, J = 6.8 Hz, 3H), (m, 2H), 0.02 (s, 9H); 13 C NMR (CDCl 3, 100MHz), δ: 139.2, 138.1, 128.6, 126.8, 126.7, S10
11 126.1, 34.1, 25.6, 24.6, 0.47; IR (film) v: 2925, 2856, 1641, 1498, 1458, 1374, 1254, 1174, 845, 748, 699 cm -1 ; HRMS (EI) (m/z): calcd for C 14 H 22 Si (M + ): ; Found: (E)-(2-cyclohexylvinyl)benzene (3j) Prepared following the Typical Procedure in 42% yield as a white liquid (15.6 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), cyclohexene 2j (32.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using petroleum ether as eluent. Ph 3j White liquid; R f = 0.7 (Petroleum ether); 1 H NMR (CDCl 3, 500MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.34 (d, J = 16.5 Hz, 1H), 6.18 (dd, J 1 = 16.0 Hz, J 2 = 7.0 Hz, 1H), (m, 1H), (m, 4H), (m, 1H), (m, 2H), (m, 2H), (m, 1H); 13 C NMR (CDCl 3, 100MHz), δ: 138.2, 137.0, 128.6, 127.3, 126.9, 126.1, 41.3, 33.1, 26.3, 26.2; IR (film) v: 3066, 3032, 2924, 2853, 1623, 1607, 1547, 1532, 1179, 1108, 1027, 921, 873, 751 cm -1 ; HRMS (EI) (m/z): calcd for C 14 H 18 (M + ): ; Found: (E)-(2-(1-methylcyclohexyl)vinyl)benzene (3k) Prepared following S11
12 the Typical Procedure in 45% yield as a white liquid (18 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), 1-methylcyclohex-1-ene 2k (38.4 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using petroleum ether as eluent. Ph 3k White liquid; R f = 0.72 (Petroleum ether); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.32 (d, J = 16.4 Hz, 1H), 6.21 (d, J = 16.4 Hz, 1H), (m, 2H), (m, 3H), (m, 4H), 1.07 (s, 3H), (m, 1H); 13 C NMR (CDCl 3, 100MHz), δ: 141.2, 138.4, 128.6, 126.8, , , 38.1, 36.3, 29.9, 26.5, 22.6; IR (film) v: 3061, 3026, 2925, 2854, 1495, 1433, 1073, 1025, 744, 692, 602 cm -1 ; HRMS (EI) (m/z): calcd for C 15 H 20 (M + ): ; Found: ((E)-styryl)bicyclo[2.2.1]heptane (3l) Prepared following the Typical Procedure in 50% yield as a white liquid (20 mg, mmol) for 3f, from β-nitrostyrene 1a (30 mg, 0.2 mmol), bicyclo[2.2.1]hept-2-ene 2l (37.6 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The S12
13 purification was performed by flash column chromatography on silica gel using petroleum ether as eluent. White liquid; R f = 0.42 (Petroleum ether); 1 H NMR (CDCl 3, 500MHz), δ: (m, 2H), (m, 2H), (m, 1H), 6.30 (d, J = 16.0 Hz, 1H), 6.13 (dd, J 1 = 16.0 Hz, J 2 = 8.0 Hz, 1H), (m, 2H), 2.15 (d, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3, 100MHz), δ: 138.1, 136.6, 128.6, 127.4, 126.8, 126.1, 45.6, 42.8, 38.1, 36.8, 36.0, 29.9, 29.2; IR (film) v: 3060, 3027, 2951, 2867, 1605, 1498, 1452, 965, 746, 697 cm -1 ; HRMS (EI) (m/z): calcd for C 15 H 18 (M + ): ; Found: (E)-1-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-4-methylbenzene (6a) Prepared following the Typical Procedure in 80% yield as a pale yellow liquid (45 mg, mmol) for 6a, from (E)-1-methyl-4-(2-nitrovinyl)benzene 1b (33 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. S13
14 OBn Me 6a Pale yellow liquid; R f = 0.39 (EtOAc/Petroleum ether 1:100) 1 H NMR (CDCl 3, 400MHz), δ: (m, 4H), (m, 3H), 7.03 (d, J = 7.6 Hz, 2H), 6.27 (d, J = 16.4 Hz, 1H), 6.16 (d, J = 16.4 Hz, 1H), 4.47 (s, 2H), 3.21 (s, 2H), 2.25 (s, 3H), 1.08 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 139.0, 137.1, 136.7, 135.2, 129.3, 128.4, , , 126.7, 126.1, 79.5, 73.4, 37.9, 24.8, 21.3; IR (film) v: 3028, 2961, 2926, 2861, 1692, 1645, 1548, 1459, 1101, 1025, 969, 800, 737, 698 cm -1 ; HRMS (EI) (m/z): calcd for C 20 H 24 O (M + ): ; Found: (E)-1-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene (6b) Prepared following the Typical Procedure as a pale yellow liquid (31mg, 53% yield). Prepared following the Typical Procedure in 53% yield as a pale yellow liquid (31 mg, mmol) for 6b, from (E)-1-methoxy-4-(2-nitrovinyl)benzene 1c (36 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:50) as eluent. S14
15 Pale yellow liquid; R f = 0.34 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 500MHz), δ: (m, 4H), (m, 3H), 6.84 (d, J = 8.5 Hz, 2H), 6.32 (d, J = 16.0 Hz, 1H), 6.15 (d, J = 16.0 Hz, 1H), 4.55 (s, 2H), 3.81 (s, 3H), 3.28 (s, 2H), 1.15 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 158.8, 139.0, 136.0, 130.8, 128.4, 127.6, 127.5, 127.3, 126.2, 114.0, 79.6, 73.4, 55.4, 37.9, 24.8; IR (film) v: 3030, 2959, 2861, 1547, 1510, 1364, 1290, 1247, 1180, 1098, 1033, 909, 853, 812 cm -1 ; HRMS (EI) (m/z): calcd for C 20 H 24 O 2 (M + ): ; Found: (E)-4-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-N,N-dimethylanili ne (6c) Prepared following the Typical Procedure in 50% yield as a pale yellow liquid (31 mg, mmol) for 6c, from (E)-N,N-dimethyl-4-(2-nitrovinyl)aniline 1d (38 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:20) as eluent. S15
16 Pale yellow liquid; R f = 0.38 (EtOAc/Petroleum ether 1:20); 1 H NMR (CDCl 3, 400MHz), δ: (m, 4H), (m, 3H), 6.67 (d, J = 8.8 Hz, 2H), 6.28 (d, J = 16.4 Hz, 1H), 6.07 (d, J = 16.4 Hz, 1H), 4.54 (s, 2H), 3.26 (s, 2H), 2.93 (s, 6H), 1.13 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 149.9, 139.1, 134.0, 128.4, 127.5, 127.4, 127.1, 126.8, 126.6, 112.8, 79.8, 73.4, 40.8, 37.8, 24.9; IR (film) v: 3028, 2962, 2927, 2858, 1610, 1521, 1452, 1354, 1164, 1103, 847, 806, 738 cm -1 ; HRMS (EI) (m/z): calcd for C 21 H 27 NO (M + ): ; Found: (E)-1-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-4-fluorobenzene (6d) Prepared following the Typical Procedure in 87% yield as a pale yellow liquid (49 mg, mmol) for 6d, from (E)-1-fluoro-4-(2-nitrovinyl)benzene 1e (34 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. S16
17 OBn F 6d Pale yellow liquid; R f = 0.32 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 400MHz), δ: (m, 7H), (m, 2H), 6.26 (d, J = 16.4 Hz, 1H), 6.12 (d, J = 16.4 Hz, 1H), 4.47 (s, 2H), 3.21 (s, 2H), 1.07 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ:162.1 (d, J = Hz), 138.9, (d, J = 2.0 Hz), (d, J = 3.0 Hz), (d, J = 62.0 Hz), 127.7, , , 125.8, (d, J = 21.0 Hz), 79.4, 73.4, 37.9, 24.8; IR (film) v: 3035, 2963, 2928, 2859, 1644, 1566, 1548, 1510, 1227, 1099, 968, 812, 736, 697 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 21 FO (M + ): ; Found: (E)-1-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-4-bromobenzene (6e) Prepared following the Typical Procedure in 58% yield as a pale yellow liquid (40 mg, mmol) for 6e, from (E)-1-bromo-4-(2-nitrovinyl)benzene 1f (45 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:50) as eluent. S17
18 Pale yellow liquid; R f = 0.28 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 500MHz), δ: 7.41 (d, J = 8.5 Hz, 2H), (m, 4H), (m, 1H), 7.22 (d, J = 8.5 Hz, 2H), 6.31 (d, J = 16.5 Hz, 1H), 6.27 (d, J = 16.0 Hz, 1H), 4.54 (s, 2H), 3.28 (s, 2H), 1.14 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 139.0, 138.9, 137.0, 131.6, 128.5, 127.8, 127.6, 125.9, 120.6, 79.3, 73.4, 38.1, 24.7; IR (film) v: 3030, 2959, 2925, 2858, 1547, 1532, 1460, 1308, 1249, 1198, 1016, 968, 909, 852, 806 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 21 BrO (M + ): ; Found: (E)-1-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-2-chlorobenzene (6f) Prepared following the Typical Procedure in 53% yield as a pale yellow liquid (32 mg, mmol) for 6f, from (E)-1-chloro-2-(2-nitrovinyl)benzene 1g (37 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:100) as eluent. S18
19 Pale yellow liquid; R f = 0.41 (EtOAc/Petroleum ether 1:100); 1 H NMR (CDCl 3, 400MHz), δ: (m, 1H), (m, 5H), (m, 1H), (m, 1H), (m, 1H), 6.79 (d, J = 16.4 Hz, 1H), 6.29 (d, J = 16.4 Hz, 1H), 4.56 (s, 2H), 3.32 (s, 2H), 1.19 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 141.0, 138.9, 136.1, 133.0, 129.7, 128.4, 128.1, 127.5, , , 123.4, 79.4, 73.4, 38.4, 24.7; IR (film) v: 3062, 3030, 2961, 2926, 2857, 1496, 1464, 1100, 1029, 744, 696 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 21 ClO (M + ): ; Found: (E)-2-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)phenol (6g) Prepared following the Typical Procedure in 50% yield as a pale yellow liquid (28 mg, mmol) for 6g, from (E)-2-(2-nitrovinyl)phenol 1h (33 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:5) as eluent. S19
20 Yellow liquid; R f = 0.42 (EtOAc/Petroleum ether 1:5); 1 H NMR (CDCl 3, 400MHz), δ: (m, 4H), (m, 2H), (m, 1H), 6.87 (t, J = 7.6 Hz, 1H), 6.80 (d, J = 8.0 Hz, 1H), 6.57 (d, J = 16.4 Hz, 1H), 6.19 (d, J = 16.4 Hz, 1H), 4.55 (s, 2H), 3.31 (s, 2H), 1.17 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 153.0, 140.6, 138.7, 128.5, 128.2, , , 127.5, 125.3, 121.5, 120.7, 115.9, 79.5, 73.5, 38.3, 24.6; IR (film) v: 3261, 3062, 3030, 2926, 1872, 1649, 1549, 1365, 1161, 942 cm -1 ; HRMS (EI) (m/z): calcd for C 19 H 22 O 2 (M + ): ; Found: (E)-4-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-1,2-dimethoxybenz ene (6h) Prepared following the Typical Procedure in 53% yield as a pale yellow liquid (34 mg, mmol) for 6h, from (E)-1,2-dimethoxy-4-(2-nitrovinyl)benzene 1i (42 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:40) as eluent. S20
21 Pale yellow liquid; R f = 0.26 (EtOAc/Petroleum ether 1:40); 1 H NMR (CDCl 3, 400MHz), δ: (m, 5H), (m, 2H), 6.81 (d, J = 8.0 Hz, 1H), 6.32 (d, J = 16.4 Hz, 1H), 6.15 (d, J = 16.4 Hz, 1H), 4.56 (s, 2H), 3.91 (s, 3H), 3.88 (s, 3H), 3.29 (s, 2H), 1.16 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 149.1, 148.4, 139.0, 136.2, 131.1, 128.4, , , 126.6, 119.2, 111.2, 108.7, 79.6, 73.4, 56.0, 55.9, 37.9, 24.8; IR (film) v: 3058, 3029, 959, 2929, 2856, 1692, 1646, 1593, 1512, 1263, 1141, 1100, 1029, 967, 738, 701 cm -1 ; HRMS (EI) (m/z): calcd for C 21 H 26 O 3 (M + ): ; Found: (E)-2-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)furan (6i) Prepared following the Typical Procedure in 53% yield as a pale yellow liquid (39 mg, mmol) for 6i, from (E)-2-(2-nitrovinyl)furan 1j (28 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:50) as eluent. S21
22 Pale yellow liquid; R f = 0.46 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 500MHz), δ: (m, 6H), (m, 1H), 6.25 (d, J = 16.5 Hz, 1H), 6.21 (d, J = 16.0 Hz, 1H), 6.16 (d, J = 3.0 Hz, 1H), 4.54 (s, 2H), 3.27 (s, 2H), 1.13 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 153.5, 141.4, 138.9, 137.0, 128.4, 127.6, 127.5, 116.0, 111.3, 106.7, 79.3, 73.4, 37.9, 24.6; IR (film) v: 3060, 3033, 2964, 2926, 2859, 1625, 1461, 1366, 1269, 1203, 1101, 1022, 803, 740, 703 cm -1 ; HRMS (EI) (m/z): calcd for C 17 H 20 O 2 (M + ): ; Found: (E)-2-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)thiophene (6j) Prepared following the Typical Procedure in 78% yield as a pale yellow liquid (42 mg, mmol) for 6j, from (E)-2-(2-nitrovinyl)thiophene 1k (31 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:50) as eluent. S22
23 Pale yellow liquid; R f = 0.46 (EtOAc/Petroleum ether 1:50); 1 H NMR (CDCl 3, 500MHz), δ: (m, 4H), (m, 1H), 7.10 (d, J = 5.0 Hz, 1H), (m, 1H), (m, 1H), 6.51 (d, J = 16.5 Hz, 1H), 6.14 (d, J = 16.0 Hz, 1H), 4.55 (s, 2H), 3.27 (s, 2H), 1.14 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 143.5, 138.9, 138.0, 128.4, 127.6, 127.5, 127.4, 124.7, 123.4, 120.5, 79.2, 73.4, 38.0, 24.7; IR (film) v: 3063, 2959, 2924, 1640, 1607, 1457, 1420, 1259, 1201, 911, 800 cm -1 ; HRMS (EI) (m/z): calcd for C 17 H 20 OS (M + ): ; Found: (E)-3-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)pyridine (6k) Prepared following the Typical Procedure in 48% yield as a yellow liquid (25.6 mg, mmol) for 6k, from (E)-3-(2-nitrovinyl)pyridine 1l (30 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:5) as eluent. S23
24 Yellow liquid; R f = 0.28 (EtOAc/Petroleum ether 1:5); 1 H NMR (CDCl 3, 400MHz), δ: 8.50 (d, J = 5.6 Hz, 2H), 7.68 (d, J = 8.0 Hz, 1H), (m, 4H), (m, 1H), (m, 1H), (m, 2H), 4.54 (s, 2H), 3.29 (s, 2H), 1.16 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 148.3, 148.1, 140.6, 138.8, 133.6, 132.7, 128.4, , , , , 79.2, 73.4, 38.2, 24.6; IR (film) v: 3030, 2962, 2927, 2859, 1568, 1532, 1100, 1025, 916, 737, 707 cm -1 ; HRMS (EI) (m/z): calcd for C 18 H 21 NO (M + ): ; Found: (E)-3-(4-(benzyloxy)-3,3-dimethylbut-1-en-1-yl)-1-tosyl-1H-indole (6l) Prepared following the Typical Procedure in 43% yield as a yellow liquid (39 mg, mmol) for 6l, from (E)-3-(2-nitrovinyl)-1-tosyl-1H-indole 1m (69 mg, 0.2 mmol), (((2-methylallyl)oxy)methyl)benzene 2a (64.8 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:5) as eluent. S24
25 OBn N Ts 6l Yellow liquid; R f = 0.36 (EtOAc/Petroleum ether 1:5); 1 H NMR (CDCl 3, 400MHz), δ: 7.91 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.4 Hz, 2H), 7.63 (d, J = 8.4 Hz, 1H), 7.46 (s, 1H), (m, 7H), 7.11 (d, J = 8.0 Hz, 2H), 6.35 (d, J = 16.4 Hz, 1H), 6.27 (d, J = 16.4 Hz, 1H), 4.47 (s, 2H), 3.22 (s, 2H), 2.23 (s, 3H), 1.09 (s, 6H); 13 C NMR (CDCl 3, 100MHz), δ: 145.0, 139.7, 138.9, 135.6, 135.3, 130.0, 129.5, 128.4, 127.6, 127.0, 124.9, 123.4, 123.1, 121.2, 120.6, 117.4, 113.8, 79.4, 73.4, 38.3, 24.7, 21.7; IR (film) v: 3057, 2962, 2925, 2857, 1548, 1450, 1370, 1269, 1175, 1124, 1096, 1025, 741, 704, 578 cm -1 ; HRMS (EI) (m/z): calcd for C 28 H 29 NO 3 S (M + ): ; Found: (S,E)-7-(3,4-dimethoxyphenyl)-3,5,5-trimethylhept-6-en-1-ol (6m) Prepared following the Typical Procedure in 54% yield as a yellow liquid (34 mg, mmol) for 6m, from (E)-1,2-dimethoxy-4-(2-nitrovinyl)benzene 1i (42 mg, 0.2 mmol), (S)-(-)-β-Citronellol 2m (62 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:3) as eluent. S25
26 Pale yellow liquid; R f = 0.26 (EtOAc/Petroleum ether 1:3); 1 H NMR (CDCl 3, 400MHz), δ: (m, 2H), 6.81 (d, J = 8.0 Hz, 1H), 6.20 (d, J = 16.0 Hz, 1H), 6.03 (d, J = 16.4 Hz, 1H), 3.91 (s, 3H), 3.87 (s, 3H), (m, 2H), 1.60 (s, 1H), (m, 9H), 1.08 (s, 6H), 0.87 (d, J = 6.4 Hz, 3H); 13 C NMR (CDCl 3, 100MHz), δ: 149.1, 148.3, 139.1, 131.4, 125.4, 118.9, 111.3, 108.8, 61.4, 56.1, 56.0, 43.7, 40.1, 38.0, 36.4, 29.6, 27.48, 27.45, 22.2, 19.8; IR (film) v: 3460, 2935, 1593, 1546, 1513, 1413, 1262, 1143, 1089, 1027, 969, 863, 805 cm -1 ; HRMS (EI) (m/z): calcd for C 20 H 32 O 3 (M + ): ; Found: ((E)-4-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-3,3-dim ethylbut-1-en-1-yl)pyridine (6n) Prepared following the Typical Procedure in 63% yield as a yellow liquid (40 mg, mmol) for 6n, from (E)-3-(2-nitrovinyl)pyridine 1l (30 mg, 0.2 mmol), (1S,2R,4R)-1-isopropyl-4-methyl-2-((2-methylallyl)oxy)cyclohexane 2n (83 mg, 0.4 mmol), Fe(acac) 3 (7.2 mg, 10 mol %), PhSiH 3 (43.2 mg, 0.4 mmol) in 2 ml EtOH for 8 h at 60 o C. The purification was performed by flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:5) as eluent. S26
27 Pale yellow liquid; R f = 0.28 (EtOAc/Petroleum ether 1:5); 1 H NMR (CDCl 3, 400MHz), δ: 8.55 (s, 1H), 8.41 (d, J = 4.0 Hz, 1H), 7.66 (dt, J 1 = 8.0 Hz, J 2 = 1.6 Hz, 1H), 7.21 (dd, J 1 = 7.6 Hz, J 2 = 4.8 Hz,, 1H), 6.37 (d, J = 16.4 Hz, 1H), 6.32 (d, J = 16.4 Hz, 1H), 3.46 (d, J = 8.4 Hz, 1H), 3.06 (d, J = 8.8 Hz, 1H), 2.99 (td, J 1 = 10.4 Hz, J 2 = 4.0 Hz, 1H), (m, 1H), (m, 1H), 1.87 (s, 1H), (m, 2H), (m, 2H), 1.13 (s, 3H), 1.12 (s, 3H), (m, 1H), 0.90 (d, J = 6.4 Hz, 3H), 0.86 (d, J = 7.2 Hz, 3H), (m, 1H), 0.72 (d, J = 6.8 Hz, 3H); 13 C NMR (CDCl 3, 100MHz), δ: 148.3, 148.0, 141.1, 133.7, 132.6, 123.5, 123.3, 79.9, 77.8, 48.4, 40.3, 38.3, 34.8, 31.7, 25.8, 24.7, 24.6, 23.5, 22.5, 21.1, 16.3; IR (film) v: 3029, 2954, 2922, 2866, 1676, 1646, 1565, 1462, 1421, 1371, 1313, 1236, 1179, 1099, 1018, 922, 849 cm -1 ; HRMS (EI) (m/z): calcd for C 21 H 33 NO (M + ): ; Found: Radical Scavenger Test A Schlenk tube containing (E)-(2-nitrovinyl)benzene (15 mg, 0.1 S27
28 mmol), Fe(acac) 3 (3.56 mg, 10 mol %), TEMPO (31 mg, 0.2 mmol) were evacuated and purged with Argon three times. Afterwards, (((2-methylallyl)oxy)methyl)benzene (32.4 mg, 0.2 mmol), PhSiH 3 (21.6 mg, 0.2 mmol) and 1 ml EtOH was added via syringe. The solution was kept at 60 o C for 8 h. The conversion was very low (< 10%). Replacing TEMPO with BHT gave the same result. S28
29 S29
30 S30
31 Ph OPh 3b CDCl 3, 400MHz S31
32 Ph OPh 3b CDCl 3,100MHz S32
33 S33
34 S34
35 S35
36 S36
37 Ph N 3e CDCl 3, 400MHz Boc S37
38 Ph N 3e CDCl 3, 100MHz Boc S38
39 S39
40 S40
41 S41
42 S42
43 S43
44 S44
45 S45
46 S46
47 S47
48 S48
49 S49
50 S50
51 S51
52 S52
53 OBn Me 6a CDCl 3, 400MHz S53
54 OBn Me 6a CDCl 3, 100MHz S54
55 S55
56 S56
57 OBn Me 2 N 6c CDCl 3, 400MHz S57
58 OBn Me 2 N 6c CDCl 3, 100MHz S58
59 S59
60 S60
61 S61
62 S62
63 S63
64 S64
65 S65
66 S66
67 S67
68 S68
69 S69
70 S70
71 OBn S 6j CDCl 3, 500MHz S71
72 OBn S 6j CDCl 3, 100MHz S72
73 S73
74 S74
75 f1 (ppm) S75
76 S76
77 S77
78 S78
79 S79
80 S80
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