Supporting Materials
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Carbonylative Coupling of Aryl Tosylates/triflates with Arylboronic Acids under CO Atmosphere Cheng Yi Hao, Dan Wang, Ya Wei Li, Lin Lin Dong, Ying Jin, Xiu Rong Zhang, Sheng Chang, Zhu, Heyun * College of Pharmacy, JiLin Medical University, JiLin , JiLin, PR China Corresponding author. Tel.: address: jmu_changsheng@126.com Supporting Materials Content General.. 2 Preparation and Characterization of Starting Materials. 2 Typical procedure for the product.. 3 Characterization data of the product... 4
2 General Starting materials were purchased from common commercial sources and all solvents were purified and dried according to standard methods prior to use. 1 H NMR spectra were recorded on a 400 M Hz spectrometer using tetramethylsilane (TMS) as internal standard. Proton chemical shifts are reported in parts per million (ppm) relative to TMS. Multiplicities are reported as: singlet (s), doublet (d), triplet (t) and multiplet (m). 13 C NMR spectra were recorded at 100 MHz using TMS as internal standard. HRMS (EI) data were collected on High Resolution mass spectrometer (ion trap). Other substrates and catalysts were commercially available and used without additional purification. Typical procedure for the product Typical procedure for carbonylative coupling with aryl tosylates Pd(TFA) O 2 dppe B(OH) 2 OTs R 1 R 2 CO (1 atm) DMA, 80 o C R 1 R 2 A mixture of arylboronic acids (0.6 mmol), aryl tosylates (0.5 mmol), Pd(TFA) 2 (5 mol%), and dppe (10 mol%) was stirred at 80 o C for 6 h in DMA (1 ml) under CO (1 atm). Afterwards, 1 ml water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et 2 O (2 ml) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO 2 column to afford the desired product(ethyl acetate/hexane). Typical procedure for carbonylative coupling with aryl triflates
3 O Pd(TFA) 2 S-phos B(OH) 2 OTf R 1 R 2 CO (1 atm) R 1 R 2 MTBE, 80 o C A mixture of arylboronic acids (0.6 mmol), aryl triflates (0.5 mmol), Pd(TFA) 2 (5 mol%), and S-phos (10 mol%) was stirred at 80 o C for 6 h in MTBE (1 ml) under CO (1 atm). Afterwards, the solution was filtered through a filter paper and the organic phase was evaporated under reduced pressure. The residue was purified on a SiO 2 column to afford the desired product(ethyl acetate/hexane). Typical procedure for the synthesis of Oxybenzone with aryl tosylates A mixture of 2,4-dimethoxy-phenylboronic acids (0.6 mmol), phenyl 4- methylbenzenesulfonate (0.5 mmol), Pd(TFA) 2 (5 mol%), and dppe (10 mol%) was stirred at 80 o C for 6 h in DMA (1 ml) under CO (1 atm). Afterwards, 1 ml water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et 2 O (2 ml) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO 2 column to afford the coupling product (93%). The purificative product was then treated by the the solution of AlCl 3 (1 mmol) in CH 2 Cl 2 (2 ml), and the mixture was stirred at room temperature for 12h. The reaction residue was then washed by HCl (1 mol/l), NaCl saturation and dried by anhydrous Na 2 SO 4. The organic phase was combined and evaporated under reduced pressure, and the residue was purified on a SiO 2 column to afford Oxybenzone (87%). Typical procedure for the synthesis of Oxybenzone with aryl triflates A mixture of 2,4-dimethoxy-phenylboronic acids (0.6 mmol), phenyl trifluoromethanesulfonate (0.5 mmol), Pd(TFA) 2 (5 mol%), and S-phos (10 mol%) was stirred at 80 o C for 6 h in MTBE (1 ml) under CO (1 atm). Afterwards, the solution was filtered through a filter paper and the organic phase was evaporated
4 under reduced pressure. The residue was purified on a SiO 2 column to afford the desired product (95%). The purificative product was then treated by the the solution of AlCl 3 (1 mmol) in CH 2 Cl 2 (2 ml), and the mixture was stirred at room temperature for 12h. The reaction residue was then washed by HCl (1 mol/l), NaCl saturation and dried by anhydrous Na 2 SO 4. The organic phase was combined and evaporated under reduced pressure, and the residue was purified on a SiO 2 column to afford Oxybenzone (88%). Typical procedure for the synthesis of Ketoprofen with aryl tosylates A mixture of 2-(3-boronophenyl)propanoic acid (0.6 mmol), phenyl 4- methylbenzenesulfonate (0.5 mmol), Pd(TFA) 2 (5 mol%), and dppe (10 mol%) was stirred at 80 o C for 6 h in DMA (1 ml) under CO (1 atm). Afterwards, 1 ml water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et 2 O (2 ml) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO 2 column to afford Ketoprofen (83%). Typical procedure for the synthesis of Ketoprofen with aryl triflates A mixture of 2-(3-boronophenyl)propanoic acid (0.6 mmol), phenyl trifluoromethanesulfonate (0.5 mmol), Pd(TFA) 2 (5 mol%), and S-phos (10 mol%) was stirred at 80 o C for 6 h in MTBE (1 ml) under CO (1 atm). Afterwards, the solution was filtered through a filter paper and the organic phase was evaporated under reduced pressure. The residue was purified on a SiO 2 column to afford Ketoprofen (86%). Characterization data of the product
5 (1) benzophenone m.p o C (lit. 2 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.80 ( d, J = 8.0 Hz, 4 H ), 7.59 ( t, J = 8.0 Hz, 2 H ), 7.46 ( t, J = 7.6 Hz, 4 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 196.7, 137.7, 132.5, 130.2, HRMS (EI) Calcd for C 13 H 10 O (M + ) , Found (2) 4-benzyloxy-benzophenone (T5-1) m.p o C (lit. 1 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.84 ( d, J = 8.0
6 Hz, 2 H ), 7.77 ( t, J = 7.6 Hz, 2 H ), 7.55 ( t, J = 7.6 Hz, 1 H ), ( m, 7 H ), 7.04 ( d, J = 8.4 Hz, 2 H ), 5.15 ( s, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.3, 162.2, 138.1, 136.2, 132.4, 131.8, 130.4, 129.8, 128.7, 128.3, 128.2, 127.4, 114.3, HRMS (EI) Calcd for C 20 H 16 O 2 (M + ) , Found (3) 4-methoxy-benzophenone (T5-2) m.p o C (lit. 4 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.83 ( d, J = 8.4 Hz, 2 H ), 7.74 ( t, J = 8.0 Hz, 2 H ), 7.57 ( t, J = 7.6 Hz, 1 H ), 7.45 ( t, J = 7.6 Hz, 2 H ), 6.97 ( d, J = 8.4 Hz, 2 H ), 3.87 ( s, 3 H ). 13 C NMR ( 100 MHz,
7 CDCl 3 ) δ 195.5, 163.1, 138.3, 132.4, 131.9, 130.2, 129.7, 128.3, 113.4, HRMS (EI) Calcd for C 14 H 12 O 2 (M + ) , Found (4) 4-benzoylbenzonitrile (T5-3) m.p o C (lit. 2 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.89 ( t, J = 8.4 Hz, 2 H ), ( m, 4 H ), 7.64 ( t, J = 7.6 Hz, 1 H ), 7.51 ( t, J = 7.2 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.2, 141.3, 136.3, 133.4, 132.2, 130.4, 130.1, 128.7, 118.1, HRMS (EI) Calcd for C 14 H 9 NO (M + ) , Found
8 (5) 4-trifluoromethyl-benzophenone (T5-4) m.p o C (lit. 1 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.91 ( d, J = 8.0 Hz, 2 H ), 7.82 ( d, J = 7.6 Hz, 2 H ), 7.76 ( d, J = 8.0 Hz, 2 H ), 7.62 ( t, J = 7.2 Hz, 1 H ), 7.52 ( t, J = 7.6 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.6, 140.8, 136.8, ( dd, J 1 = 64.2 Hz, J 2 = 32.2 Hz ), 133.2, ( d, J = 3.9 Hz ), 128.6, ( dd, J 1 = 7.2 Hz, J 2 = 3.6 Hz ), ( d, J = Hz ). HRMS (EI) Calcd for C 14 H 9 F 3 O (M + ) , Found
9 (6) 4-nitrobenzophenone (T5-5) m.p o C (lit. 1 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 8.35 ( d, J = 7.6 Hz, 2 H ), 7.94 ( d, J = 7.6 Hz, 2 H ), 7.82 ( d, J = 7.6 Hz, 2 H ), 7.65 ( t, J = 7.6 Hz, 1 H ), 7.52 ( t, J = 7.6 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 194.8, 149.9, 142.9, 136.3, 133.5, 130.8, 130.2, 128.7, HRMS (EI) Calcd for C 13 H 9 NO 3 (M + ) , Found
10 (7) 4-fluorobenzophenone (T5-6) m.p o C (lit. 3 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.85 ( dd, J 1 = 8.2 Hz, J 2 = 5.2 Hz, 2 H ), 7.76 ( d, J = 7.6 Hz, 2 H ), 7.58 ( t, J = 7.2 Hz, 1 H ), 7.49 ( t, J = 7.6 Hz, 2 H ), 7.17 ( t, J = 8.0 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.4, (d, J = 248 Hz), 137.5, 133.8, 132.8(d, J = 9.2 Hz), 132.6, 129.9, 128.4, (d, J = 20 Hz). HRMS (EI) Calcd for C 13 H 9 FO (M + ) , Found
11 (8) 4-chloro-benzophenone (T5-7) m.p o C (lit. 2 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.78 ( d, J = 8.4 Hz, 4 H ), 7.59 ( t, J = 7.6 Hz, 1 H ), 7.47 ( t, J = 7.6 Hz, 2 H ), 6.95 ( d, J = 8.8 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.2, 161.1, 137.9, 133.4, 132.3, 129.9, 129.4, 128.4, HRMS (EI) Calcd for C 13 H 9 ClO (M + ) , Found
12 (9) 4-bromobenzophenone (T5-8) m.p o C (lit. 4 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ (m, 4 H ), 7.54 ( t, J = 7.2 Hz, 1 H ), 7.43 ( t, J = 7.2 Hz, 2 H ), 6.66 ( d, J = 8.0 Hz, 2 H ). 13 C NMR (100 MHz, CDCl 3 ) δ 195.5, 151.0, 138.9, 132.9, 131.5, 129.6, 128.2, 127.4, HRMS (EI) Calcd for C 13 H 9 BrO (M + ) , Found
13 (10) 3,5-difluorobenzophenone (T5-9) m.p o C (lit. 3 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.80 ( d, J = 7.2 Hz, 2 H ), 7.64 ( t, J = 7.2 Hz, 1 H ), 7.52 ( t, J = 7.6 Hz, 2 H ), 7.32 ( dd, J 1 = 7.2 Hz, J 2 = 2.4 Hz, 2 H ), 7.05 ( tt, J 1 = 8.4 Hz, J 2 = 2.4 Hz, 1 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ , ( dd, J 1 = 250 Hz, J 2 = 11.7 Hz ), ( t, J = 7.2 Hz ), , , , , ( dd, J 1 = 18.3 Hz, J 2 = 7.3 Hz ), ( t, J = 25.1 Hz ). HRMS (EI) Calcd for C 13 H 8 F 2 O (M + ) , Found
14 (11) 2,5-difluorobenzophenone (T5-10) m.p o C (lit. 3 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.83 ( d, J = 8.4 Hz, 2 H ), 7.63 ( tt, J 1 = 7.2 Hz, J 2 = 1.6 Hz, 1 H ), 7.49 ( d, J = 7.6 Hz, 2 H ), ( m, 2 H ), ( m, 1 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 192.1, 159.7, (d, J = 253 Hz), 136.8, 133.8, 129.9, 128.7, ( dd, J 1 = 16.8 Hz, J 2 = 6.4 Hz ), ( dd, J 1 = 23.2 Hz, J 2 = 8.6 Hz ), ( dd, J 1 = 24.0 Hz, J 2 = 8.0 Hz ), ( dd, J 1 = 18.2 Hz, J 2 = 7.2 Hz ), ( dd, J 1 = 25.2 Hz, J 2 = 3.2 Hz ). HRMS (EI) Calcd for C 13 H 8 F 2 O (M + ) , Found
15 (12) 3,4-dichlorobenzophenone (T5-11) m.p o C (lit. 4 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.91 ( s, 1 H ), 7.77 ( d, J = 7.6 Hz, 2 H ), 7.64 ( t, J = 8.0 Hz, 2 H ), 7.59 ( d, J = 8.4 Hz, 1 H ), 7.52 ( t, J = 7.6 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 194.3, 137.3, 137.1, 136.7, 133.1, 131.9, 130.5, 129.9, 129.1, HRMS (EI) Calcd for C 13 H 8 Cl 2 O (M + ) , Found
16 (13) 2-bromo-benzophenone (T5-12) m.p o C (lit. mp 42 C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.63 ( d, J = 7.2 Hz, 2 H ), 7.51 ( t, J = 7.2 Hz, 1 H ), ( m, 3 H ), 7.28 ( t, J = 8.4 Hz, 1 H ), 6.72 ( d, J = 8.4 Hz, 1 H ), 6.59 ( t, J = 8.0 Hz, 1 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 199.1, 150.9, 140.2, 134.7, 134.3, 131.1, 129.2, 128.2, 118.2, 117.1, HRMS (EI) Calcd for C 13 H 9 BrO (M + ) , Found
17 (14) 2-benzoylbenzonitrile (T5-13) m.p o C (lit. mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ8.06 ( d, J = 7.6 Hz, 1 H ), ( m, 3 H ), 7.54 ( dd, J 1 = 14.0 Hz, J 2 = 7.2 Hz, 2 H ), ( m, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.2, 170.9, 142.6, 136.9, 133.3, 133.2, 130.9, 129.6, 129.5, 128.5, 127.9, HRMS (EI) Calcd for C 14 H 9 NO (M + ) , Found
18 (15) 2,3,4,5,6-pentamethyl-benzophenone (T5-14) m.p o C (lit. 7 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.83 ( d, J = 7.2 Hz, 2 H ), 7.56 ( t, J = 7.2 Hz, 1 H ), 7.42 ( t, J = 7.6 Hz, 2 H ), 2.27 ( s, 3 H ), 2.22 ( s, 6 H ), 2.02 ( s, 6 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 202.1, 137.7, 135.6, 133.5, 132.9, 129.6, 129.1, 128.8, 17.6, 16.7, HRMS (EI) Calcd for C 18 H 20 O (M + ) , Found
19 (16) 2,3,4,5,6-perfluoro-benzophenone (T5-15) m.p o C (lit. 8 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.87 ( d, J = 7.6 Hz, 2 H ), 7.71 ( t, J = 7.6 Hz, 1 H ), 7.56 ( t, J = 7.2 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 185.4, 135.9, 135.1, 129.8, HRMS (EI) Calcd for C 13 H 5 F 5 O (M + ) , Found
20 (17) 4-benzoylpyridine (T5-16) m.p o C (lit. 9 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.78 ( d, J = 8.4 Hz, 4 H ), 7.57 ( t, J = 7.6 Hz, 1 H ), 7.47 ( t, J = 7.6 Hz, 2 H ), 6.88 ( d, J = 8.4 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.1, 161.0, 137.9, 133.2, 132.3, 129.9, 129.3, 128.3, HRMS (EI) Calcd for C 12 H 9 NO (M + ) , Found
21 (18) 3-Benzoylpyridine (T5-17) m.p o C (lit. 11 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 8.98 ( s, 1 H ), 8.80 ( d, J = 5.2 Hz, 1 H ), 8.12 ( d, J = 8.0 Hz, 1 H ), ( m, 6 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 194.7, 152.8, 150.8, 137.1, 136.5, 133.1, 133.0, 130.0, 128.5, HRMS (EI) Calcd for C 12 H 9 NO (M + ) , Found
22 (19) 2-benzoylpyridine (T5-18) m.p o C (lit. 9 mp 42 C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 8.72 ( d, J = 4.8 Hz, 1 H ), ( m, 3 H ), 7.89 ( t, J = 7.6 Hz, 1 H ), 7.59 ( d, J = 7.6 Hz, 1 H ), 7.49 ( t, J = 7.6 Hz, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ , , , , , , , , , HRMS (EI) Calcd for C 12 H 9 NO (M + ) , Found
23 (20) 3,5-bis(trifluoromethyl)benzophenone (T6-5) m.p o C (lit. 14 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 8.24 ( s, 2 H ), 8.11 ( s, 1 H ), 7.81 ( d, J = 7.6 Hz, 2 H ), 7.68 ( t, J = 8.0 Hz, 1 H ), 7.54 ( d, J = 7.6 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 193.6, 139.4, 136.0, 133.7, ( dd, J 1 = 65.2 Hz, J 2 = 32.6 Hz ), 130.0, 129.9, 128.9, ( t, J = 4.0 Hz ), 124.3, ( q, J = 269 Hz ). HRMS (EI) Calcd for C 15 H 8 F 6 O (M + ) , Found
24 (21) 4-methylbenzophenone (T6-6) m.p o C (lit. 1 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.80 ( d, J = 6.8 Hz, 2 H ), 7.74 ( d, J = 7.6 Hz, 2 H ), 7.57 ( t, J = 7.2 Hz, 1 H ), 7.48 ( t, J = 7.6 Hz, 2 H ), 7.28 ( d, J = 8.0 Hz, 2 H ), 2.47 ( s, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 196.6, 143.3, 137.9, 134.9, 132.2, 130.4, 129.9, 129.0, 128.3, HRMS (EI) Calcd for C 14 H 12 O (M + ) , Found
25 (22) 3,4-dimethylbenzophenone (T6-7) m.p o C (lit. 4 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.81 ( d, J = 8.0 Hz, 2 H ), 7.65 ( s, 1 H ), ( m, 2 H ), 7.48 ( t, J = 7.6 Hz, 2 H ), 7.24 ( t, J = 8.0 Hz, 1 H ), 2.37 ( s, 3 H ), 2.34 ( s, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 196.9, 141.9, 138.2, 136.7, 135.3, 132.2, 131.4, 129.9, 129.4, 128.2, 128.0, 20.1, HRMS (EI) Calcd for C 15 H 14 O (M + ) , Found
26 (23) 2-methylbenzophenone (T6-8) 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.82 ( d, J = 8.0 Hz, 2 H ), 7.60 ( t, J = 7.6 Hz, 1 H ), 7.48 ( t, J = 7.6 Hz, 2 H ), 7.42 ( t, J = 7.6 Hz, 1 H ), ( m, 3 H ), 2.35 (s, 3H). 13 C NMR ( 100 MHz, CDCl 3 ) δ 198.7, 138.7, 137.8, 136.8, 133.2, 131.0, 130.3, 130.2, 128.5, 128.4, 125.2, HRMS (EI) Calcd for C 14 H 12 O (M + ) , Found
27 (24) 3-chloro-benzophenone (T6-10) m.p o C (lit. 5 mp 84 C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.81 ( d, J = 7.6 Hz, 2 H ), 7.57 ( t, J = 7.6 Hz, 1 H ), 7.45 ( t, J = 7.6 Hz, 2 H ), 7.24 ( t, J = 8.0 Hz, 1 H ), 7.13 ( d, J = 7.2 Hz, 2 H ), 6.88 ( d, J = 8.4 Hz, 1 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.1, 146.6, 138.7, 137.8, 132.4, 130.1, 129.1, 128.3, 120.7, 119.1, HRMS (EI) Calcd for C 13 H 9 ClO (M + ) , Found
28 (25) 2-chlorobenzophenone (T6-11) m.p o C (lit. 2 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.81 ( d, J = 8.4 Hz, 2 H ), 7.61 ( t, J = 7.6 Hz, 1 H ), ( m, 4 H ), ( m, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.7, 138.7, 136.5, 133.7, 131.4, 131.2, 130.1, 129.2, 128.7, HRMS (EI) Calcd for C 13 H 9 ClO (M + ) , Found
29 (26) 4-hydroxy-benzophenone (T6-12) m.p o C (lit. 9 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.81 ( br, 1 H ), 7.78 ( d, J = 8.4 Hz, 4 H ), 7.59 ( t, J = 7.2 Hz, 1 H ), 7.47 ( t, J = 7.2 Hz, 2 H ), 6.84 ( d, J = 8.8 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.1, 161.0, 137.9, 133.3, 132.2, 129.9, 129.3, 128.4, HRMS (EI) Calcd for C 13 H 10 O 2 (M + ) , Found
30 (27) 4-aminobenzophenone (T6-13) m.p o C (lit. 5 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ (m, 4 H ), 7.53 ( t, J = 7.2 Hz, 1 H ), 7.45 ( t, J = 7.2 Hz, 2 H ), 6.67 ( d, J = 8.0 Hz, 2 H ), 4.28 ( br, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 195.5, 150.9, 138.9, 132.8, 131.5, 129.6, 128.2, 127.4, HRMS (EI) Calcd for C 13 H 11 NO (M + ) , Found
31 (28) 3-aminobenzophenone (T6-14) m.p o C (lit. 10 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ7.79 ( d, J = 7.6 Hz, 2 H ), 7.58 ( t, J = 7.6 Hz, 1 H ), 7.46 ( t, J = 7.6 Hz, 2 H ), 7.22 ( t, J = 8.0 Hz, 1 H ), 7.13 ( d, J = 7.2 Hz, 2 H ), 6.87 ( d, J = 8.8 Hz, 1 H ), 3.75 ( br, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 197.1, 146.6, 138.7, 137.8, 132.4, 130.1, 129.1, 128.3, 120.6, 119.1, HRMS (EI) Calcd for C 13 H 11 NO (M + ) , Found
32 (29) 2-aminobenzophenone (T6-15) m.p o C (lit. 11 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.64 ( d, J = 7.2 Hz, 2 H ), 7.51 ( t, J = 7.6 Hz, 1 H ), ( m, 3 H ), 7.27 ( t, J = 8.4 Hz, 1 H ), 6.72 ( d, J = 8.4 Hz, 1 H ), 6.58 ( t, J = 8.0 Hz, 1 H ), 6.01 (br, 2H). 13 C NMR ( 100 MHz, CDCl 3 ) δ 199.2, 150.9, 140.2, 134.7, 134.3, 131.1, 129.2, 128.2, 118.2, 117.1, HRMS (EI) Calcd for C 13 H 11 NO (M + ) , Found
33 (30) 2-benzoylthiophene (T6-17) m.p o C (lit. 11 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 7.85 ( t, J = 7.6 Hz, 2 H ), 7.72 ( d, J = 5.6 Hz, 1 H ), 7.65 ( d, J = 4.8 Hz, 1 H ), 7.58 ( t, J = 7.2 Hz, 1 H ), 7.49 ( t, J = 7.2 Hz, 2 H ), 7.15 ( t, J = 4.8 Hz, 1 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 188.3, 143.6, 138.2, 134.9, 134.3, 132.3, 129.2, 128.5, HRMS (EI) Calcd for C 11 H 8 OS (M + ) , Found
34 (31) Phenyl(pyrimidin-5-yl)methanone (T6-18) m.p o C (lit. 10 mp C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 8.24 ( s, 2 H ), 8.11 ( s, 1 H ), 7.80 ( d, J = 7.6 Hz, 2 H ), 7.67 ( t, J = 7.6 Hz, 1 H ), 7.56 ( d, J = 7.6 Hz, 2 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 193.7, 139.5, 135.8, 133.7, 131.6, 130.1, 125.6, 124.0, HRMS (EI) Calcd for C 11 H 8 N 2 O (M + ) , Found
35 (32) Oxybenzone m.p o C (lit. 12 mp 66 C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ ( s, 1 H ), ( m, 2 H ), 7.65 ( t, J = 7.2 Hz, 1 H ), ( m, 3 H ), 6.51 ( d, J = 2.4 Hz, 1 H ), 6.40 ( dd, J = 9.2 Hz, 2.4 Hz, 1 H ), 3.85 ( s, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 200.0, 166.4, 166.2, 138.3, 135.3, 131.5, 128.9, 128.3, 113.1, 107.4, 101.4, HRMS (EI) Calcd for C 14 H 12 O 3 (M + ) , Found
36 (33) Ketoprofen m.p o C (lit. 13 mp 94 C); 1 H NMR ( 400 MHz, CDCl 3, TMS ) δ 9.89 ( s, 1 H ), ( m, 3 H ), 7.68 ( d, J = 7.6 Hz, 1 H ), ( m, 2 H ), ( m, 3 H ), 3.82 ( q, J = 7.2 Hz, 1 H ), 1.55 ( d, J = 7.2 Hz, 3 H ). 13 C NMR ( 100 MHz, CDCl 3 ) δ 196.6, 180.2, 140.1, 137.9, 137.4, 132.6, 131.7, 130.1, 129.4, 129.3, 128.6, 128.3, 45.2, HRMS (EI) Calcd for C 16 H 14 O 3 (M + ) , Found
37 Reference 1. Qin, W.; Yasuike, S.; Kakusawa, N.; Kurita, J. J. Organomet. Chem. 2008, 693(17), Liu, G.; Cai, M. Catal. Commun. 2007, 8(3), Rao, M. L. N.; Venkatesh, V.; Banerjee, D. Tetrahedron 2007, 63(52), Jin, T.-S.; Yang, M.-N.; Feng, G.-L.; Li, T.-S. Synth. Commun. 2004, 34(3), Clark, M. T.; Hendley, E. C.; Neville, O. K. J. Am. Chem. Soc. 1955, 77, Yi, W.-B.; Cai, C. J. Fluor. Chem. 2005, 126, Fuson, R. C.; McKusick, B. C.; Mills, J. J. Org. Chem. 1946, 11, Barbour, A. K.; Buxton, M. W.; Coe, P. L.; Stephens, R.; Tatlow, J. C. J. Chem. Soc. 1961, Maerten, E.; Sauthier, M.; Mortreux, A.; Castanet, Y. Tetrahedron 2006, 63(3), 682.
38 10. Ebert, G. W.; Rieke, R. D. J. Org. Chem. 1988, 53, Cai, M.; Zheng, G.; Zha, L.; Peng, J. Eur. J. Org. Chem. 2009, (10), Jeon, H.-K.; Sarma, S. N.; Kim, Y.-J.; Ryu, J.-C. Toxicology 2008, 248(10), Aziz, H.-Y.; Eslam. P.; Mohammad, D.-J. Bull. Korean Chem. Soc. 2008, 29(4), 833.
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