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1 Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2016 Supporting Information Fangyi Li, Changgui Zhao, and Jian Wang* Department of Pharmacology and Pharmaceutical Sciences, School of dicine, Tsinghua University, Beijing, , China. Contents: 1. General Information S2 2. Experimental Procedure S3 3. MR Spectra S22
2 1. General Information Unless otherwise stated, all commercial reagents were used as received. Reactions were conducted in dry glassware using anhydrous solvents (pass through activated alumina columns). Reaction temperatures were controlled using IKAmag temperature modulator, and unless stated otherwise, reactions were performed at room temperature (rt, approximately, 24 o C). Thin-layer chromatography (TLC) was conducted on plates (GF254) supplied by Yantai Chemicals (China) and visualized using a combination of UV, anisaldehyde, iodine, and potassium permanganate staining. Silica gel ( mesh) supplied by Tsingdao aiyang Chemicals (China) was used for flash column chromatography. 1, 13 C and 19 F MR spectra were recorded on Bruker spectrometers (400 Mz). Chemical shifts were reported in parts per million (ppm), and the residual solvent peak was used as an internal reference: proton (chloroform δ 7.26), carbon (chloroform δ 77.16) or tetramethylsilane (TMS δ 0.00) was used as a reference. Multiplicity was indicated as follows: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), dd (doublet of doublet), bs (broad singlet). Coupling constants were reported in ertz (z). All high resolution mass spectra were obtained from the Tsinghua University Mass Spectrometry Facility. S2
3 2. Experimental Procedure The C precatalyst C (0.02 mmol), KC 3 (0.04 mmol) and compound 1a (0.2 mmol) were placed in an oven-dried Schlenk tube equipped with a magnetic stir bar. The tube was closed with a septum, evacuated and refilled with argon. Dry TF (4.0 ml) were added. The reaction mixture stirred at room temperature till the starting material was completely consumed (monitored by TLC or GC-MS). The mixture was concentrated under reduced pressure and purified by flash chromatography eluted with hexane/etac = 10:1 to afford the corresponding desired product 2a as white solid (33 mg, 87% yield). 1-Acetyl-4-phenylazet-2(1)-one (2a): 33mg, 87% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.96 (d, J = 6 z, 1), (m, 3), 6.52 (s, 1), 2.50 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , 21.94; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z t Bu 4-Phenyl-1-pivaloylazet-2(1)-one (2b): 35mg, 77% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.01 (d, J = 7.2 z, 2), (m, 3), 6.51 (s, 1), 1.42 (s, 9); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , 38.70, 27.82; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z S3
4 Ph 1-Benzoyl-4-phenylazet-2(1)-one (2c): 41mg, 83% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.35 (d, J = 8 z, 2), 8.09 (d, J = 6.8 z, 2), (m, 1), (m, 5), 6.59 (s, 1); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , ; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z Acetyl-4-(p-tolyl)azet-2(1)-one (2d): 31 mg, 78% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.89 (d, J = 8.4 z, 2), 7.30 (d, J = 8.4 z, 2), 6.49 (s, 1), 2.50 (s, 3), 2.44 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , 21.91, 21.66; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z F 1-Acetyl-4-(4-fluorophenyl)azet-2(1)-one (2e): 36 mg, 87% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.98 (t, J = 7.6 z, 2), 7.15 (t J = 8.4 z, 2), 6.46 (s, 1), 2.49 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , (d, J = 252 z), , , (d, J = 3.1 z), (d, J = 8.9 z), (d, J = 21.8 z), , 21.93; 19 F MR (376 Mz, CDCl 3 ) δ (ppm): ; RMS (ESI) exact mass calculated for [M+a] + (C 11 8 F 2 a) requires m/z , S4
5 found m/z Cl 1-Acetyl-4-(4-chlorophenyl)azet-2(1)-one (2f): 37 mg, 84% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.91 (d, J = 8.4 z, 2), 7.44 (d, J = 8.4 z, 2), 6.49 (s, 1), 2.49 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , 21.94; RMS (ESI) exact mass calculated for [M+a] + (C 11 8 Cl 2 a) requires m/z , found m/z C 2 thyl 4-(1-acetyl-4-oxo-1,4-dihydroazet-2-yl)benzoate (2g): 40 mg, 81% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.26 (d, J = 8.4 z, 2), 8.03 (d, J = 8.4 z, 2), 6.58 (s, 1), 3.95 (s, 3), 2.51 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , 52.56, 21.97; RMS (ESI) exact mass calculated for [M+a] + (C a 4 a) requires m/z , found m/z CF 3 1-Acetyl-4-(4-(trifluoromethyl)phenyl)azet-2(1)-one (2h): 45 mg, 88% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.08 (d, J = 8 z, 2), 7.73 (d J = 8 z, 2), 6.58 (s, 1), 2.52 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , (q, J = 32.6 z), , S5
6 (q, J = 3.7 z), (q, J = z), , 21.96; 19 F MR (376 Mz, CDCl 3 ) δ (ppm): 63.02; RMS (ESI) exact mass calculated for [M+] + (C 12 9 F 3 2 ) requires m/z , found m/z Acetyl-4-(4-nitrophenyl)azet-2(1)-one (2i): 38 mg, 83% yield; White solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.33 (d, J = 8.4 z, 2), 8.14 (d, J = 8.8 z, 2), 6.63 (s, 1), 2.53 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , 22.01; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z Ph 4-([1,1'-Biphenyl]-4-yl)-1-acetylazet-2(1)-one (2j): 44 mg, 84% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.05 (d, J = 8.4 z, 2), 7.71 (d, J = 8.4 z, 2), 7.64 (d, J = 7.2 z, 2), 7.48 (t, J = 7.2 z, 2), (m, 1), 6.56 (s, 1), 2.51 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , , 21.95;; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z S6
7 1-Acetyl-4-(m-tolyl)azet-2(1)-one (2k): 31 mg, 78% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): (m, 2), (m, 2), 6.49 (s, 1), 2.49 (s, 3), 2.42 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 21.90, 21.56; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z Acetyl-4-(3-methoxyphenyl)azet-2(1)-one (2l): 32 mg, 73% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): (m, 2), 7.37 (t, J = 8.4 z, 1), (m, 1), 6.49 (s, 1), 3.86 (s, 3), 2.48 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 55.52, 21.90; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z ; Cl 1-Acetyl-4-(3-chlorophenyl)azet-2(1)-one (2m): 40 mg, 91% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.99 (t, J = 2 z, 1), 7.81 (dt, J 1 = 7.6 z, J 2 = 1.2 z, 1), (m, 1) 7.41 ( t, J = 7.6 z, 1), 6.51 (s, 1), 2.50 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 21.96; RMS (ESI) exact mass calculated for [M+] + (C 11 9 Cl 2 ) requires m/z , found m/z ; Br 1-Acetyl-4-(3-bromophenyl)azet-2(1)-one (2n): 43 mg, 80% yield; white solid; 1 MR (400 Mz, S7
8 CDCl 3 ) δ (ppm): 8.14 (s, 1), 7.85 (d, J = 8 z, 1), 7.63 (d, J = 8 z, 1),7.34 (t, J = 8 z, 1), 6.50 (s, 1), 2.50 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 21.94; RMS (ESI) exact mass calculated for [M+a] + (C 11 8 Br 2 a) requires m/z , found m/z CF 3 1-Acetyl-4-(3-(trifluoromethyl)phenyl)azet-2(1)-one (2o): 44 mg, 86% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.26 (s, 1), 8.11 (d, J = 7.6 z, 1), 7.76 (d, J = 7.6 z, 1), 7.61 (t, J = 7.6 z, 1), 6.57 (s, 1), 2.52 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , (q, J = 32.6 z), , , (q, J = 3.5 z), (q, J = 3.8 z), (q, J = z), , 21.92; 19 F MR (376 Mz, CDCl 3 ) δ (ppm): 62.94; RMS (ESI) exact mass calculated for [M+a] + (C 12 8 F 3 2 a) requires m/z , found m/z C 3-(1-Acetyl-4-oxo-1,4-dihydroazet-2-yl)benzonitrile (2p): 33 mg, 79% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.32 (s, 1), 8.15 (d, J = 8 z, 1), 7.79 (d, J = 7.6 z, 1), 7.61 (t, J = 8 z, 1), 6.55 (s, 1), 2.52 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , 21.98; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z S8
9 1-Acetyl-4-(naphthalen-1-yl)azet-2(1)-one (2q): 30 mg, 63% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): (m, 1), 7.97 (d, J = 8 z, 1), (m, 1), 7.67 (d, J = 7.2 z, 1), (m, 3), 6.45 (s, 1), 2.55 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , , , , 29.84; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z acetyl-4-(naphthalen-2-yl)azet-2(1)-one (2r): 41 mg, 86% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.60 (s, 1), 7.96 (d, J = 7.6 z, 1), 7.90 (brs, 2), 7.87 (d, J = 7.6 z, 1), 7.56 (m, 2), 6.63 (s, 1), 2.53 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , , , , 21.96; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z Ts 1-Acetyl-4-(1-tosyl-1-indol-3-yl)azet-2(1)-one (2s): 52 mg, 69% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.42 (s, 1), 8.02 (d, J = 8 z, 1), 7.93 (d, J = 7.6 z, 1), 7.84 (d, J = 8.4z, 2), (m, 2), 7.26 (d, J = 8 z, 2), 6.49 (s, 1), 2.49 (s, 3), 2.35 (s, 3); 13 C MR S9
10 (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , , , , , , 21.85, 21.75; RMS (ESI) exact mass calculated for [M+a] + (C Sa) requires m/z , found m/z Ts 1-Acetyl-4-(1-tosyl-1-pyrrol-2-yl)azet-2(1)-one (2t): 43 mg,65% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.71 (d, J = 8.4 z, 2), (m, 1), 7.30 (d, J = 8 z, 2), (m, 1), 6.41 (s, 1), 6.37 (t, J = 3.6 z, 1), 2.42 (s, 3), 2.29 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , , , 21.83, 21.48; RMS (ESI) exact mass calculated for [M+a] + (C Sa) requires m/z , found m/z Acetyl-4-((3r,5r,7r)-adamantan-1-yl)azet-2(1)-one (2u): 37 mg, 76% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 5.90 (s, 1), 2.38 (s, 3), 2.07 (brs, 3), (m, 12); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , 39.51, 38.77, 36.60, 28.15, RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z S10
11 1-Acetyl-3,4-dihydronaphtho[1,2-b]azet-2(1)-one (2v): 13 mg, 31% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 8.07 (d, J = 7.2 z, 1), (m, 2), 7.22 (d, J = 7.2 z, 1), 2.92 (t, J = 8 z, 2), 2.77 (t, J = 8 z, 2), 2.46 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 26.85, 21.69, 19.69; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z acetyl-1-indeno[1,2-b]azet-2(3)-one (2w): 15 mg, 38% yield; white solid; 1 MR (400 Mz, CDCl 3 ) δ (ppm): 7.89 (d, J = 7.2 z, 1), 7.60 (d, J = 7.6 z, 1), (m, 2), 3.80 (s, 2), 2.55 (s, 3); 13 C MR (100 Mz, CDCl 3 ) δ (ppm): , , , , , , , , , , 33.15, 21.91; RMS (ESI) exact mass calculated for [M+a] + (C a) requires m/z , found m/z S11
12 3. MR Spectra: 1-Acetyl-4-phenylazet-2(1)-one (2a): S12
13 4-Phenyl-1-pivaloylazet-2(1)-one (2b): t Bu S13
14 t Bu 1-Benzoyl-4-phenylazet-2(1)-one (2c): Ph S14
15 Ph 1-Acetyl-4-(p-tolyl)azet-2(1)-one (2d): S15
16 1-Acetyl-4-(4-fluorophenyl)azet-2(1)-one (2e): F S16
17 F F 1-Acetyl-4-(4-chlorophenyl)azet-2(1)-one (2f): S17
18 Cl Cl thyl 4-(1-acetyl-4-oxo-1,4-dihydroazet-2-yl)benzoate (2g): S18
19 C 2 C 2 1-Acetyl-4-(4-(trifluoromethyl)phenyl)azet-2(1)-one (2h) S19
20 CF 3 CF 3 S20
21 CF 3 1-Acetyl-4-(4-nitrophenyl)azet-2(1)-one (2i): 2 S21
22 2 4-([1,1'-biphenyl]-4-yl)-1-acetylazet-2(1)-one (2j): Ph S22
23 Ph 1-Acetyl-4-(m-tolyl)azet-2(1)-one (2k): S23
24 1-Acetyl-4-(3-methoxyphenyl)azet-2(1)-one (2l) S24
25 1-Acetyl-4-(3-chlorophenyl)azet-2(1)-one (2m): F Cl S25
26 Cl 1-Acetyl-4-(3-bromophenyl)azet-2(1)-one (2n): Br S26
27 Br 1-Acetyl-4-(3-(trifluoromethyl)phenyl)azet-2(1)-one (2o): CF 3 S27
28 CF 3 CF 3 3-(1-Acetyl-4-oxo-1,4-dihydroazet-2-yl)benzonitrile (2p): S28
29 C C 1-Acetyl-4-(naphthalen-1-yl)azet-2(1)-one (2q) S29
30 1-Acetyl-4-(naphthalen-2-yl)azet-2(1)-one (2r) S30
31 1-Acetyl-4-(1-tosyl-1-indol-3-yl)azet-2(1)-one (2s): S31
32 Ts Ts 1-Acetyl-4-(1-tosyl-1-pyrrol-2-yl)azet-2(1)-one (2t): S32
33 Ts Ts 1-Acetyl-4-((1s,3s)-adamantan-1-yl)azet-2(1)-one (2u) S33
34 1-Acetyl-3,4-dihydronaphtho[1,2-b]azet-2(1)-one (2v): S34
35 1-Acetyl-1-indeno[1,2-b]azet-2(3)-one (2w): S35
36 S36
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