Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
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1 Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi Ye, Zhicheng Liu, and Gangguo Zhu* Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua , P. R. China Contents General Information Synthesis and Characterization of 1 General Procedure for Synthesis of 3 Characterization of 3 Derivatization of Products to 5 and 6 References Copies of NMR Spectra Decomposition Experiment S2-S3 S3-S6 S7 S7-S17 S18-S19 S19 S20-S70 S71 S1
2 General Information: 1 H, 13 C and 19 F NMR spectra were recorded on 600 or 400 spectrometer using CDCl 3 as the solvent. Chemical shifts were referenced relative to residual solvent signal (CDCl 3 : 1 H NMR: δ 7.26 ppm, 13 C NMR: δ ppm). The following abbreviations are used to describe peak patterns where appropriate: br = broad, s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet. Coupling constants (J) are reported in Hertz (Hz). HRMS were performed on a TF MS apparatus (ESI). Melting points were measured with micro melting point apparatus. Unless otherwise noted, materials obtained from commercial suppliers were used directly without further purification. 2-(3-Arylpropioloyl)benzaldehydes 1 1 were prepared in our own way. CH 1a t Bu CH 1b Me CH 1c CH 1d CH 1e Me CH 1f Me CH 1g Me Me CH 1h Me Me Me CH 1i Ph CH 1j F CH 1k Cl CH 1l CH 1m S F CH 1n S F CH 1o t Bu Cl CH 1p t Bu S2
3 Synthesis and Characterization of 1: 1 In a 100 ml flask with a stir-bar was charged with o-bromobenzaldehyde (20 mmol) and p-tsh (2 mmol). MeH (40 ml) and trimethyl orthoformate (50 mmol) were added and the solution was heated to 70 o C for 3-8 hours. Aqueous NaHC 3 solution (3 mmol) was then added and most of the THF was evaporated. The solution was extracted with ethyl acetate (20 ml * 3). The combined organic layer was dried over anhydrous Na 2 S 4, concentrated to afford the o-bromoacetal product (4.6 g, 100% yield), which was used in the next step without further purification. S3
4 To a 50 ml flask charged with o-bromoacetal (20 mmol) was added anhydrous THF (20 ml), and cooled to -78 o C. n-buli (24 mmol, 2.5 M in hexane) was then added over 30 min to the solution and the reaction was kept at -78 o C for another 1 h. Next, DMF (60 mmol) was added to the reaction solution over 20 min. The combined organic layer was then warmed to RT and kept for 1 h. The solution was then quenched with saturated aqueous NH 4 Cl (20 ml), extracted with ethyl acetate (30 ml * 3). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na 2 S 4. Then it was concentrated and the residue was subject to flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:10) as eluent to give the aldehyde product (2.9 g, 80% yield). To a 50 ml two-necked flask charged with phenylacetylene/phenylbromoacetylene (6 mmol) was evacuated and backfilled with Argon. Then anhydrous THF (20 ml) was added and cooled to -78 o C. n-buli (6 mmol, 2.5 M in hexane) was then added in 30 min to the solution and the reaction was kept at -78 o C for another 1 h. The above aldehyde (5 mmol) was added and the mixture was allowed to warmed to RT and kept for 1h. The solution was then quenched with saturated aqueous NH 4 Cl (20 ml), extracted with ethyl acetate (30 ml * 3). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na 2 S 4. Then it was concentrated and the residue was used in the next step without further purification. To a 100 ml flask charged with the above secondary alcohol (4 mmol) was added anhydrous DCM (30 ml) and Mn 2 (40 mmol). The solution was kept vigorously stirring at room temperature for 10 h. Afterwards, the solution was filtered by diatomite and the filtrate was concentrated. The residue was diluted with THF (20 ml) and aqueous HCl solution (20 ml, 2 N). Afterwards, the solution was kept stirring at RT for 3 h. The residue was extracted with ethyl acetate (30 ml* 2), washed with saturated NaCl, dried over anhydrous Na 2 S 4. Then it was concentrated and the residue was subject to flash column chromatography on silica gel using ethyl acetate/petroleum ether (v/v, 1:10) as eluent to give product 2-(3-phenylpropioloyl)benzaldehyde 1a (0.73 g, 78% yield for the above two steps). S4
5 For selected characterization of substrates 1, see: 2-(3-(4-(tert-butyl)phenyl)propioloyl)benzaldehyde (1a). Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ (s, 1H), 8.31 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz 1H), 7.93 (d, J = 7.8 Hz, 1H), (m, 2H), 7.62 (d, J = 8.4 Hz, 2H), 7.45(d, J = 8.4 Hz, 2H), 1.34 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 192.3, 178.5, 155.3, 138.7, 137.5, 133.4, 133.3, 132.9, 132.0, 128.5, 126.0, 116.6, 95.4, 87.7, 35.3, 31.1; HRMS (ESI) (m/z): calcd for C 20 H 18 2 ([M+H] + ), ; found (3-(2,6-dimethylphenyl)propioloyl)benzaldehyde (1d). White solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ (s, 1H), 8.35 (d, J = 7.2 Hz, 1H), 7.95 (dd, J = 7.2 Hz, 1H), (m, 2H), (m, 4H), 7.28 (t, J = 7.2 Hz, 1H), 7.12 (d, J = 7.6 Hz, 2H), 2.56 (s, 6H); 13 C NMR (100MHz, CDCl 3 ) δ 192.2, 178.5, 143.1, 138.9, 137.5, 133.3, 132.9, 131.8, 130.9, 128.6, 127.4, 119.6, 95.9, 92.6; HRMS (ESI) (m/z): calcd for C 18 H 14 2 ([M+H] + ), ; found (3-(4-methoxyphenyl)propioloyl)benzaldehyde (1e). Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ (s, 1H), 8.28 (d, J = 7.2 Hz, 1H), 7.89 (d, J = 6.6 Hz, 1H), (m, 4H), 6.91 (d, J = 7.8 Hz, 2H), 3.84 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 192.3, 178.4, 162.2, 138.8, 137.4, 135.5, 133.2, 132.8, 131.9, 128.4, 114.6, 111.3, 96.1, 87.9, 55.6; HRMS (ESI) (m/z): calcd for C 17 H 12 3 ([M+H] + ), ; found S5
6 2-(3-(3-phenoxyphenyl)propioloyl)benzaldehyde (1i). Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ (s, 1H), 8.28 (dd, J 1 = 7.2 Hz, J 2 = 1.8 Hz 1H), 7.92 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), (m, 4H), 7.26 (s, 1H), (m, 2H), 7.03 (dd, J 1 = 8.4 Hz, J 2 = 1.2 Hz, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 192.1, 178.4, 157.8, 156.2, 138.3, 137.5, 133.6, 132.9, 132.1, 130.2, 128.6, 127.9, 124.3, 121.8, 121.0, 119.5, 93.6, 87.6; HRMS (ESI) (m/z): calcd for C 22 H 14 3 ([M+H] + ), ; found (3-(4-fluorophenyl)propioloyl)benzaldehyde (1j). White solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ (s, 1H), 8.27 (d, J = 7.8 Hz, 1H), 7.90 (d, J = 6.6 Hz, 1H), (m, 4H), 7.11 (t, J = 8.4 Hz, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 192.1, 178.3, (d, J = Hz), 138.4, 137.5, 135.7, 133.5, 132.9, 128.6, 116.5, 115.7; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 16 H 9 F 2 ([M+H] + ), ; found (3-(4-(tert-butyl)phenyl)-1-methoxyprop-2-yn-1-yl)benzaldehyde (1aa). Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ (s, 1H), 7.92 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz 1H), 7.83 (d, J = 7.8 Hz, 1H), 7.62 (dt, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 7.52 (dt, J 1 = 7.2 Hz, J 2 = 0.6 Hz, 1H) 7.40 (m, 2H), 7.34 (m, 2H), 5.97 (s, 1H), 3.57 (s, 3H), 1.30 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 192.2, 152.2, 140.4, 134.0, 133.8, 131.6, 131.4, 129.0, 128.8, 125.5, 119.3, 89.1, 85.6, 70.7, 56.8, 34.9, 31.3; HRMS (ESI) (m/z): calcd for C 21 H 22 2 ([M+H] + ), ; found S6
7 General Procedure for Synthesis of 3: To a solution of 1a (58 mg, 0.2 mmol) and 2e (126.4 mg, 0.4 mmol) in 2 ml of dry MeCN was added CuBr (5.7 mg, 0.04 mmol) and K 2 C 3 (27.6 mg, 0.2 mmol) under a N 2 atmosphere. After stirring at 60 o C for 10 h, the reaction mixture was cooled to room temperature and concentrated. Column purification on silica gel using ethyl acetate/petroleum ether (v/v = 1:10) as the eluent gave the desired product 3a as a yellow oil (45.8 mg, 64% yield). Characterization of Products 3: 2-(4-(tert-butyl)phenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3a): Starting from 1a (290 mg, 1.0 mmol) and following the general procedure, 222 mg (62% yield) of 3a was obtained as a yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.19 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), 8.12 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), 7.48 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 8.4 Hz, 2H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 183.8, 180.9, 153.0, 149.5, 134.7, 134.4, (q, J = 27.2 Hz), 131.8, 131.3, (q, J = 1.5 Hz), 128.1, 127.1, 126.6, 124.8, (q, J = Hz), 34.9, 31.2; 19 F NMR (565MHz, CDCl 3 ) δ 56.20; HRMS (ESI) (m/z): calcd for C 21 H 17 F 3 2 ([M+H] + ), ; found S7
8 2-(p-tolyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3b): mg, 61% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.19 (dd, J 1 = 7.8 Hz, J 2 = 1.8 Hz, 1H), (m, 1H), (m, 2H), 7.28 (d, J = 7.8 Hz, 1H), 7.14 (d, J = 7.8 Hz, 1H), 2.43 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 183.8, 181.0, 149.6, 140.1, 134.8, 134.5, (q, J = 27.2 Hz), 131.9, 131.4, (q, J = 1.5 Hz), 128.7, 128.3, 127.1, 126.7, (q, J = Hz), 21.6; 19 F NMR (565MHz, CDCl 3 ) δ CF 3 3c 2-(o-tolyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3c): 41.1 mg, 65% yield; Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.23 (dd, J 1 = 7.2 Hz, J 2 = 0.6 Hz, 1H), 8.12 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), (m, 1H), (m, 2H), 7.02 (d, J = 7.2 Hz, 1H), 2.15 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 183.4, 180.7, 150.3, (q, J = 1.5 Hz), 134.9, 134.7, (q, J = 27.2 Hz), 132.0, 131.8, 131.4, 130.0, 129.5, (q, J = 3.0 Hz), 127.2, 127.0, 125.5, (q, J = Hz), 20.1; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 18 H 11 F 3 2 ([M+H] + ), ; found (2,6-dimethylphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3d): 41.6 mg, 63% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.27 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz 1H), 8.16 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 7.90 (dt, J = 1.8 Hz, 1H), 7.86 (dt, J = 1.8 Hz, 1H), 7.28 (d, J = 7.8 Hz, 1H), 7.4 (d, J = 7.8 Hz, 2H), 2.12 (s, 6H); 13 C NMR (151MHz, CDCl 3 ) δ 183.2, 180.4, 150.1, 135.0, 134.7, 134.3, 132.0, 131.6, 131.5, 129.0, 127.5, 127.3, 127.2, 127.0, (q, J = Hz), 20.2; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 19 H 13 F 3 2 ([M+H] + ), ; found S8
9 2-(4-methoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3e): mg, 60% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.18 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 8.13 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), 7.21 (d, J = 9.0 Hz, 2H), 6.99 (d, J = 7.8 Hz, 2H), 3.87 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 184.0, 181.1, 161.2, 149.0, 134.8, 134.5, (q, J = 28.7 Hz), 131.4, (q, J = 1.5 Hz), 130.7, 127.2, 126.7, 123.3, (q, J = Hz), 113.6, 55.5; 19 F NMR (565MHz, CDCl 3 ) δ (2-methoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3f): 43.1 mg, 65% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.20 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), 8.12 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), (m, 1H), (m, 2H), 6.98 (d, J = 8.4 Hz, 1H), 3.76 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 183.0, 180.8, 156.4, 147.7, 134.6, 134.4, (q, J = 27.2 Hz), 132.0, 131.7, 131.2, 129.4, 127.1, 126.8, (q, J = Hz), 121.1, 120.3, 110.8, 55.8; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 18 H 11 F 3 3 ([M+H] + ), ; found (3,4-dimethoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3g): 41.2 mg, 57% yield; Red oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.17 (dd, J 1 = 7.8 Hz, J 2 = 1.8 Hz, 1H), 8.11 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), 6.94 (d, J = 8.4 Hz, S9
10 1H), 6.84 (dd, J 1 = 8.4 Hz, J 2 = 2.4 Hz, 1H), 6.79 (d, J = 1.8 Hz, 1H), 3.94 (s, 3H), 3.89 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 183.8, 181.1, 150.7, 148.5, 134.8, 134.5, (q, J = 27.2 Hz), 131.9, 131.4, 127.2, 126.7, 123.5, 122.6, (q, J = Hz), 112.7, 110.6, 56.08, 56.02; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 19 H 13 F 3 4 ([M+H] + ), ; found (trifluoromethyl)-3-(3,4,5-trimethoxyphenyl)naphthalene-1,4-dione (3h): 49.4 mg, 62% yield; Red solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.17 (dd, J 1 = 7.8 Hz, J 2 = 1.8 Hz, 1H), 8.11 (dd, J 1 = 7.2 Hz, J 2 = 1.8 Hz, 1H), (m, 2H), 6.46 (s, 2H), 3.91 (s, 3H), 3.85 (s, 6H); 13 C NMR (151MHz, CDCl 3 ) δ 183.6, 180.9, 152.9, 149.3, 139.4, 134.9, 134.7, (q, J = 27.2 Hz), 131.8, 131.3, 127.2, 126.8, 126.4, (q, J = Hz), 106.6, 61.1, 56.3; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 20 H 15 F 3 5 ([M+H] + ), ; found (3-phenoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3i): 47.2 mg, 60% yield; Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.18 (dd, J 1 = 7.8 Hz, J 2 = 1.8 Hz, 1H), 8.12 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), 7.42 (t, J = 7.8 Hz, 1H), (m, 2H), (m, 2H), 7.06 (d, J = 7.8 Hz, 2H), 6.95 (d, J = 7.8 Hz, 1H), 6.87 (t, J = 1.8 Hz, 1H); 13 C NMR (151MHz, CDCl 3 ) δ 183.4, 180.7, 157.0, 156.8, 148.8, 135.0, 134.7, 133.1, 132.8, 131.8, 131.3, 130.0, 129.5, 127.2, 126.9, 123.8, 123.4, (q, J = Hz), 119.9, 119.3, 119.0; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 23 H 13 F 3 3 ([M+H] + ), ; found S10
11 CF 3 3j F 2-(4-fluorophenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3j): 36.4 mg, 57% yield; Yellow solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ 8.21 (dd, J 1 = 7.6 Hz, J 2 = 1.6 Hz, 1H), 8.14 (dd, J 1 = 6.8 Hz, J 2 = 2.0 Hz, 1H), (m, 2H), (m, 2H), (m, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 183.6, 180.7, (d, J = Hz), 148.5, 135.0, 134.7, (q, J = 27.2 Hz), 131.9, 131.3, 131.0, 127.1, 126.9, (q, J = Hz), 115.4, 115.3; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 17 H 8 F 4 2 ([M+H] + ), ; found (4-chlorophenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3k): 36.9 mg, 55% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.19 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz 1H), 8.12 (dd, J 1 = 7.2 Hz, J 2 = 1.6 Hz, 1H), (m, 2H), (m, 2H), (m, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 183.4, 180.6, 148.3, 136.2, 135.1, 134.8, (q, J = 27.2 Hz), 131.8, 131.2, 130.2, 129.6, 128.4, 127.2, 126.9, (q, J = Hz); 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 17 H 8 ClF 3 2 ([M+H] + ), ; found phenyl-3-(trifluoromethyl)naphthalene-1,4-dione (3l): 34.4 mg, 57% yield; Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.20 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 8.12 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), (m, 2H), (m, 3H), (m, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 183.7, 180.9, 149.5, 134.9, 134.6, (q, J = 27.2 Hz), 131.9, 131.4, 131.3, 129.8, (q, J = 1.6 Hz), 128.0, 127.2, 126.8, S11
12 (q, J = Hz); 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 17 H 9 F 3 2 ([M+H] + ), ; found (thiophen-2-yl)-3-(trifluoromethyl)naphthalene-1,4-dione (3m): 25.8 mg, 42% yield; Yellow oil; 1 H NMR (600MHz, CDCl 3 ) δ 8.19 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 8.15 (dd, J 1 = 7.2 Hz, J 2 = 1.8 Hz, 1H), (m, 3H), 7.35 (d, J = 4.2 Hz, 1H), (m, 1H); 13 C NMR (151MHz, CDCl 3 ) δ 183.3, 180.8, 143.2, 135.1, 134.6, 133.8, 133.4, 131.9, (q, J = 27.2 Hz), 131.1, 129.8, 127.3, 127.1, 126.8, (q, J = Hz); 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 15 H 7 F 3 2 S ([M+H] + ), ; found fluoro-2-(thiophen-2-yl)-3-(trifluoromethyl)naphthalene-1,4-dione (3n): 25.4 mg, 39% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.23 (dd, J 1 = 9.0 Hz, J 2 = 5.4 Hz, 1H), (m, 2H), (m, 1H), 7.35 (d, J = 3.6 Hz, 1H), (m, 1H); 13 C NMR (151MHz, CDCl 3 ) δ 182.4, 179.5, (d, J = Hz), 143.3, 133.9, 133.6, (q, J = 3.02 Hz), (q, J = 28.7 Hz), 130.2, 129.5, 128.5, 127.2, (d, J = 22.6 Hz), (q, J = Hz), (d, J = 24.2 Hz); 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 15 H 6 F 4 2 S ([M+H] + ), ; found (4-(tert-butyl)phenyl)-6-fluoro-3-(trifluoromethyl)naphthalene-1,4-dione (3o): 45.0 mg, 60% yield; Yellow solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ 8.24 (dd, J 1 = 8.8 Hz, J 2 = 5.2 Hz, 1H), 7.76 (dd, J 1 = 8.0 Hz, J 2 = 2.4 Hz, 1H), S12
13 (m, 3H), 7.17 (d, J = 8.4 Hz, 2H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 183.0, 179.8, (d, J = Hz), 153.4, 149.7, (d, J = 9.1 Hz), (q, J = 28.7 Hz), (d, J = 9.1 Hz), (q, J = 1.5 Hz), 128.5, 127.9, 125.0, (d, J = 22.7 Hz), (q, J = Hz), (d, J = 22.7 Hz), 35.0, 31.3; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 21 H 16 F 4 2 ([M+H] + ), ; found (4-(tert-butyl)phenyl)-6-chloro-2-(trifluoromethyl)naphthalene-1,4-dione (3p): 50.9 mg, 65% yield; Yellow oil; 1 H NMR (400MHz, CDCl 3 ) δ 8.14 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.78 (dd, J 1 = 8.4 Hz, J 2 = 2.4 Hz, 1H), 7.48 (d, J = 8.4 Hz, 2H), 7.17 (d, J = 8.4 Hz, 2H), 1.37 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 183.0, 180.1, 153.4, 149.6, 141.7, 134.9, (q, J = 27.2 Hz), 132.5, 130.1, 128.8, 128.6, 127.8, 127.1, 125.0, (q, J = Hz), 35.0, 31.3; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 21 H 16 ClF 3 2 ([M+H] + ), ; found (4-(tert-butyl)phenyl)-7-(trifluoromethyl)naphtho[2,3-d][1,3]dioxole-5,8-dione (3q): 37.8 mg, 47% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 7.53 (s, 1H), 7.47 (s, 1H), (m, 2H), 7.45 (d, J = 9.0 Hz, 2H), 7.15 (d, J = 8.4 Hz, 2H), 6.17 (s, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 182.7, 180.0, 153.3, 153.0, 149.2, 133.3, (q, J = 27.2 Hz), 129.1, (q, J = 1.5 Hz), 128.5, 126.0, 124.9, (q, J = Hz), 106.3, 106.0, 103.0, 35.0, 31.4; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 22 H 17 F 3 4 ([M+H] + ), ; found S13
14 6-fluoro-2-(o-tolyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3r): 42.0 mg, 63% yield; Yellow solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ 8.30 (dd, J 1 = 8.4 Hz, J 2 = 4.8 Hz, 1H),7.78 (dd, J 1 = 8.4 Hz, J 2 = 2.8 Hz, 1H), 7.54 (dt, J 1 = 8.0 Hz, J 2 = 2.4 Hz, 1H), 7.40 (dt, J 1 = 7.6 Hz, J 2 = 0.8 Hz, 1H), (m, 2H), 7.04 (d, J = 7.2 Hz, 1H), 2.17 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 182.5, 179.4, (d, J = Hz), 150.4, 135.0, (d, J = 7.6 Hz), (q, J = 27.2 Hz), 131.4, 130.5, 130.4, 130.1, 129.6, 128.5, (q, J = 1.5 Hz), 125.6, (d, J = 22.6 Hz), (q, J = Hz), (d, J = 2.3 Hz), 20.0; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 18 H 10 F 4 2 ([M+H] + ), ; found fluoro-3-(o-tolyl)-2-(trifluoromethyl)naphthalene-1,4-dione (3s): 36.8 mg, 55% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.09 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 2H), 7.05 (dd, J 1 = 7.8 Hz, J 2 = 0.6 Hz, 1H), 2.19 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 180.9, (d, J = 3.0 Hz), (d, J = Hz), 151.2, (d, J = 9.1 Hz), 135.1, 133.5, (q, J = 28.7 Hz), 131.4, 130.0, 129.6, 127.6, 125.5, (d, J = 21.1 Hz), 123.3, (q, J = Hz), (d, J = 6.0 Hz), 20.1; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 18 H 10 F 4 2 ([M+H] + ), ; found CF 3 Cl 3t S14
15 6-chloro-3-(o-tolyl)-2-(trifluoromethyl)naphthalene-1,4-dione (3t): 49 mg, 70% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.16 (dd, J 1 = 8.4 Hz, J 2 = 0.6 Hz, 1H), 8.07 (d, J = 2.4 Hz, 1H), 7.80 (dd, J 1 = 8.4 Hz, J 2 = 1.8 Hz, 1H), 7.38 (dt, J 1 = 7.8 Hz, J 2 = 1.8 Hz, 1H), 7.29 (m, 2H), 7.01 (dd, J 1 = 7.2 Hz, J 2 = 1.2 Hz, 1H), 2.14 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 182.1, 179.6, (d, J = Hz), 156.4, 147.9, (d, J = 8.3 Hz), (q, J = 28.1 Hz), 182.4, 179.7, 150.2, 141.8, 135.0, (q, J = 27.2 Hz), 132.5, 131.4, 131.0, 130.1, 129.6, 128.8, 127.5, 127.1, 126.4, 125.6, (q, J = Hz), 20.0; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 18 H 10 ClF 3 2 ([M+H] + ), ; found (p-tolyl)-2,6-bis(trifluoromethyl)naphthalene-1,4-dione (3u): 43.7 mg, 57% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.40 (s, 1H), 8.33 (d, J = 8.4 Hz, 1H), 8.08 (dd, J 1 = 7.8 Hz, J 2 = 1.2 Hz, 1H), 7.29 (d, J = 7.8 Hz, 2H), 7.14 (d, J = 7.8 Hz, 2H), 2.45 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 182.7, 180.0, 150.0, 140.6, (q, J = 33.2 Hz), 134.0, (q, J = 28.7 Hz), 131.8, (q, J = 4.5 Hz), 130.0, (q, J = 3.0 Hz), , , (q, J = 3.0 Hz), 124.0, 122.1, (q, J = Hz), 21.6; 19 F NMR (565MHz, CDCl 3 ) δ -55.3, -63.4; HRMS (ESI) (m/z): calcd for C 19 H 10 F 6 2 ([M+H] + ), ; found fluoro-3-(2-methoxyphenyl)-2-(trifluoromethyl)naphthalene-1,4-dione (3v): 40.6 mg, 58% yield; Yellow solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.24 (dd, J 1 = 8.4 Hz, J 2 = 4.8 Hz, 1H), 7.75 (dd, J 1 = 8.4 Hz, J 2 = 2.4 Hz, 1H), (m, 2H), (m, 2H), 6.98 (d, J = 8.4 Hz, 1H), 3.76 (s, 3H); 13 C NMR S15
16 (151MHz, CDCl 3 ) δ 182.1, 179.6, (d, J = Hz), 156.4, 147.9, (d, J = 8.3 Hz), (q, J = 28.1 Hz), 131.4, (d, J = 9.1 Hz), 129.4, 128.6, (d, J = 22.7 Hz), (q, J = Hz), 120.8, 120.4, (d, J = 23.6 Hz), 110.8, 55.8; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 18 H 10 F 4 3 ([M+H] + ), ; found fluoro-2-(2-methoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3w): 42 mg, 60% yield; Yellow solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ 8.16 (dd, J 1 = 8.8 Hz, J 2 = 5.2 Hz, 1H), 7.83 (dd, J 1 = 8.4 Hz, J 2 = 2.4 Hz, 1H), (m, 2H), (m, 2H), 6.98 (d, J = 8.4 Hz, 1H), 3.76 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 181.7, 179.8, (d, J = Hz), 156.4, 148.0, (d, J = 7.6 Hz), (q, J = 27.2 Hz), 131.3, (d, J = 9.1 Hz), 129.4, 128.3, (d, J = 22.7 Hz), (q, J = Hz), 120.8, 120.3, (d, J = 24.2 Hz), 110.8, 55.8; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 18 H 10 F 4 3 ([M+H] + ), ; found chloro-2-(4-methoxyphenyl)-3-(trifluoromethyl)naphthalene-1,4-dione (3x): 38.1 mg, 52% yield; Yellow solid; Mp: o C; 1 H NMR (400MHz, CDCl 3 ) δ 8.14 (d, J = 2.0 Hz, 1H), 8.08 (d, J = 8.4 Hz, 1H), 7.74 (dd, J 1 = 8.4 Hz, J 2 = 2.0 Hz, 1H), 7.20 (d, J = 8.4 Hz, 2H), 6.99 (d, J = 8.8 Hz, 2H), 3.88 (s, 3H); 13 C NMR (151MHz, CDCl 3 ) δ 182.9, 179.9, 161.3, 149.2, 141.9, 134.5, 132.9, (q, J = 27.2 Hz), 131.0, 129.5, 128.9, 126.6, 122.8, (q, J = Hz), 113.5, 55.4; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 18 H 10 ClF 3 3 ([M+H] + ), ; found S16
17 6-chloro-2-(trifluoromethyl)-3-(3,4,5-trimethoxyphenyl)naphthalene-1,4-dione (3y): 61.3 mg, 72% yield; Red solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.14 (d, J = 8.4 Hz, 1H), 8.08 (d, J = 8.4 Hz, 1H), 7.80 (dd, J 1 = 8.4 Hz, J 2 = 1.8 Hz, 1H), 6.45 (s, 2H), 3.93 (s, 3H), 3.66 (s, 6H); 13 C NMR (151MHz, CDCl 3 ) δ 182.8, 180.0, 153.0, 149.3, 141.8, 139.7, 135.1, (q, J = 28.7 Hz), 132.4, 130.1, 128.6, 127.1, 126.0, (q, J = Hz), 106.7, 61.4, 56.4; 19 F NMR (565MHz, CDCl 3 ) δ , ; HRMS (ESI) (m/z): calcd for C 20 H 14 ClF 3 5 ([M+H] + ), ; found methoxy-2-(trifluoromethyl)-3-(3,4,5-trimethoxyphenyl)naphthalene-1,4-dione (3z): 39.6 mg, 47% yield; Red solid; Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 8.12 (d, J = 9.0 Hz, 1H), 7.51 (d, J = 9.0 Hz, 1H), 7.29 (dd, J 1 = 9.0 Hz, J 2 = 5.0 Hz, 1H), 6.45 (s, 2H), 3.96 (s, 3H), 3.92 (s, 3H), 3.86 (s, 6H); 13 C NMR (151MHz, CDCl 3 ) δ 183.9, 179.9, 164.7, 153.0, 149.9, 139.4, 133.3, (d, J = 27.2 Hz), 129.4, 126.6, 125.4, (q, J = Hz), 121.6, 110.2, 106.6, 61.1, 56.3, 56.2; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 21 H 17 F 3 6 ([M+H] + ), ; found S17
18 Derivatization of naphthoquinone 3a: 3 To a solution of naphthoquinone 3a (71.6 mg, 0.2 mmol) in 5 ml of EtH was added Na 2 C 3 (318 mg, 1.5 equiv), and H 2 2 (30%, 1.5 equiv). After stirring at 45 o C for 2 h, the reaction mixture was diluted with CH 2 Cl 2 and filtered by a short pad of silica gel. Column chromatography on silica gel using ethyl acetate/petroleum ether (v/v = 1:5) as the eluent gave product 4 (60 mg, 80% yield) as a yellow oil. 1 H NMR (600MHz, CDCl 3 ) δ 8.06 (dd, J 1 = 7.2 Hz, J 2 = 1.8 Hz, 1H), (m, 1H), (m, 2H), (m, 2H), 7.40 (dd, J 1 = 8.4 Hz, J 2 = 1.8 Hz, 1H), 7.26 (d, J = 7.8 Hz, 1H ), 1.36 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 188.7, 179.5, 186.6, 152.9, (d, J = 12.1 Hz), 132.0, 131.6, 127.9, 127.8, 127.4, 125.7, 125.2, 124.4, (q, J = Hz), 68.6, 64.1 (q, J = 33.2 Hz), 35.0, 31.4; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 21 H 17 F 3 3 ([M+H] + ), ; found To a solution of 3a (71.6 mg, 0.2 mmol) in 2 ml of DCM was added DIBAL-H (0.5 ml, 1.2 M in hexane) at -78 o C. After stirring at -78 o C for 30 mins, the reaction mixture was quenched by aqueous solution of Rochelle s salt (2 ml), then extracted with DCM, washed with brine and dried over Na 2 S 4. Column chromatography on silica gel using ethyl acetate/petroleum ether (v/v = 1:2) as eluent gave product 5 (52.5 mg, 70%) as a white solid. Mp: o C; 1 H NMR (600MHz, CDCl 3 ) δ 7.48 (d, J = 7.2 Hz, 1H), (m, 5H), 7.21 (d, J = 8.4 Hz, 2H), 5.34 (s, 1H), 5.09 (s, 1H), 1.35 (s, 9H); 13 C NMR (151MHz, CDCl 3 ) δ 149.0, 136.0, 134.5, 129.0, 128.9, 128.8, S18
19 128.75, 128.7, 128.5, (q, J = 1.5 Hz), 125.4, (q, J = Hz), 71.2, 64.9, 34.8, 31.4; 19 F NMR (565MHz, CDCl 3 ) δ ; HRMS (ESI) (m/z): calcd for C 21 H 21 F 3 2 ([M+H] + ), ; found Reference: [1] Wang, D.; Ye, X.; Shi, X. rg. Lett. 2010, 12, [2] Wang, X.; Ye, Y.; Ji, G.; Xu, Y.; Zhang, S.; Feng, J.; Zhang, Y.; Wang, J. rg. Lett. 2013, 15, [3] Claessens, S.; Habonimana, P.; Kimpe, N. D. rg. Biomol. Chem. 2010, 8, S19
20 NMR Spectra S20
21 S21
22 S22
23 S23
24 1j CH F S24
25 S25
26 S26
27 S27
28 CF 3 3b CF 3 3b S28
29 CF 3 3b S29
30 S30
31 S31
32 S32
33 CF 3 3e Me CF 3 3e Me S33
34 S34
35 CF 3 3f S35
36 S36
37 S37
38 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 CF 3 3q t Bu S51
52 S52
53 S53
54 S54
55 S55
56 S56
57 CF 3 F 3 C 3u S57
58 S58
59 CF 3 F 3v S59
60 S60
61 S61
62 Cl CF 3 3x Me S62
63 Cl 3y CF 3 Me Me Me S63
64 S64
65 Me 3z CF 3 Me Me Me Me 3z CF 3 Me Me Me S65
66 S66
67 CF 3 4 t Bu S67
68 S68
69 19 F NMR of the radical trapping experiments with PhCF 3 as the internal standard TEMP (2.0 equiv) CH 1a + standard conditions 3a + N I CF 3 t Bu 2e CF 3 0% 6, 16% ( 19 F NMR) S69
70 19 F NMR of the radical trapping experiments with PhCF 3 as the internal standard CH 1a + t Bu 2e Ph (2.0 equiv) 1' standard conditions I CF 3 3a 0% + CF 3 7, 43% ( 19 F NMR) S70
71 Decomposition experiment percent /% t/h Figure S1. Monitoring the decomposition reaction of product 3s by GC with naphthalene as the internal standard under standard reaction conditions at indicated time. H F 8 ([M-H] - ) calcd for C 17 H 10 F 3, Figure S2. bservation of the decomposition product 8 by HRMS. S71
Hualong Ding, Songlin Bai, Ping Lu,* Yanguang Wang*
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