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

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