Supporting Information
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- Ἀβειρὼν Γιαννακόπουλος
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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 15 Supporting Information For Visible-light-induced photocatalytic oxytrifluoromethylation of -allylamides for the synthesis of -containing oxazolines and benzoxazines Qiao-Hui Deng, a Jia-Rong Chen,* a Qiang Wei, a Quan-Qing Zhao, a Liang-Qiu Lu a and Wen-Jing Xiao* a,b [a] Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China ormal University, 152 Luoyu Road, Wuhan, Hubei 4379, China [b] State Key Laboratory of Applied rganic Chemistry Lanzhou University, Lanzhou 73, China chenjiarong@mail.ccnu.edu.cn; wxiao@mail.ccnu.edu.cn S1
2 Table of Contents 1. General Information 2. Materials 3. Detailed ptimization of Reaction Conditions 4. Time Profile of otocatalytic xytrifluoromethylation of 1a with 2a 5. Crystal Structure of 5f 6. Preparation and Date of Substrates 7. General Procedures and Data of Products 8. Copies of 1 H MR, 13 C MR Spectra and 19 F MR S2
3 1. General Information 1 H MR, 13 C MR and 19 F MR spectra were recorded on /6 MHz spectrophotometers. Chemical shifts (δ) are reported in parts per million (ppm) relative to residual solvent signals (CDCl 3, 7.26 ppm for 1 H MR, CDCl 3, 77. ppm for 13 C MR). Data are reported as follows: chemical shift (δ), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublets, dt = doublet of triplets, m = multiplet, br = broad signal), coupling constants (Hz). Mass spectra were measured on MS spectrometer (EI) or LC/MS/MS (ESI-MS). HRMS was recorded on Bruker ultraflextreme MALDI-TF/TF mass spectrometer. 2. Materials Unless otherwise noted, materials were purchased from commercial suppliers and used without further purification. All the solvents were treated according to general methods. 1 Flash column chromatography was performed using -3 mesh silica gel. The -allylamides were prepared according to literature procedures from commercially available substrates. 2,3 References 1 D. D. Perrin, W. L. F.Armarego, Purification of Laboratory Chemicals, 4th ed.; Pergamon Press, xford, A. Jaganathan, A. Garzan, D. C. Whitehead, R. J. Staples and B. Borhan, Angew. Chem. Int. Ed., 11, 5, Y.-M. Wang, J. Wu, C. Hoong, V. Rauniyar and F. D. Toste, J. Am. Chem. Soc., 12, 134, S3
4 3. Detailed ptimization of Reaction Conditions Table S1. Studies of the effect of photocatalysts a entry Catalyst t (h) yield (%) b 1 Ru(bpy) 3 Cl. 2 6H Ir(ppy) 2 (dtbbpy)pf Ir(dF( )ppy) 2 (dtbbpy)pf fac-ir(ppy) EosinY 5 6 Ir(ppy) 2 (bpy)pf Ru(bpm) 3 (BArF) ,4,6-triphenylpyrylium tetrafluoroborate 5 9 Ru(bpy) 3 (PF 6 ) a Reaction conditions: 1a (.1 mmol), 2a (.11 mmol), catalyst (5 mol%), a 2 HP 4 (.2 mmol) in CH 3 C (1. ml) under Ar with 3 W blue LEDs irradiation at room temperature. b GC yield using biphenyl as an internal standard. S4
5 Table S2. Studies of the effect of solvents a entry solvent t (h) yield (%) b 1 CH 3 C DMF DMS CH 2 Cl CHCl DCE EtH 5 8 Toluene 5 9 THF Et 2 24 a Reaction conditions: 1a (.1 mmol), 2a (.11 mmol), Ru(bpy) 3 (PF 6 ) 2 (5 mol%), a 2 HP 4 (.2 mmol) in the solvent (1. ml) under Ar with 3 W blue LEDs irradiation at room temperature. b GC yield using biphenyl as an internal standard. S5
6 Table S3. Studies of the effect of bases a entry base t (h) yield (%) b 1 a 2 HP ahc K 2 C Cs 2 C ah t BuK 5 7 K 2 HP a Reaction conditions: 1a (.1 mmol), 2a (.11 mmol), Ru(bpy) 3 (PF 6 ) 2 (5 mol%), Base (.2 mmol) in the CH 3 C (1. ml) under Ar with 3 W blue LEDs irradiation at room temperature. b GC yield using biphenyl as an internal standard. S6
7 4. Time profile of photocatalytic oxytrifluoromethylation of 1a with 2a The oxytrifluoromethylation of 1a was performed with/without visible light irradiation. The time profile is shown in Figure S1. As a result, continuous irradiation of visible light is essential for efficient reaction. Furthermore, the result of this experiment suggests that radical chain propagation mechanism isn t main component in this reaction. 1 visible light irradiation dark Yield (%) 6 dark dark dark Time (min) Figure S1. S7
8 5. Crystal Structure of 5f Figure S2. 6. Spectral Data of Substrates 2,4,6-Trimethyl--(2-phenylallyl)benzamide (1f) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.48 (d, J = 7.2 Hz, 2H), 7.35 (t, J = 7.4 Hz, 2H), 7.3 (s, 1H), 6.77 (s, 2H), 5.63 (br s, 1H), 5.48 (s, 1H), 5.34 (s, 1H), 4.56 (d, J = 5.6 Hz, 2H), 2.23 (s, 3H), 2.13 (s, 6H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 17.2, 144.4, 138.2, 138.2, 134.6, 134.1, 128.4, 128., 128., 126.2, 114.6, 43.3,.9, 18.9; HRMS (ESI): calculated for [C 19 H 21 +a] + requires , found (2-phenylallyl)furan-2-carboxamide (1g) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.48 (d, J = Hz, 2H), 7.39 (s, 1H), 7.36 (t, J = 7.4 Hz, 2H), 7.3 (t, J = 7.3 Hz, 1H), 7.12 (d, J = 3. Hz, 1H), 6.48 (s, 1H), 6.45 (br s, 1H), 5.52 (s, 1H), 5.31 (s, 1H), 4.5 (d, J = 5.8 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 158.1, 147.6, 143.9, 143.8, 138.2, 128.4, 128., 125.9, 114.2, 113.8, 112., 42.6; HRMS (ESI): calculated for [C 14 H a] + requires , found (2-(4-methoxyphenyl)allyl)benzamide (1j) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.71 (d, J = 7.6 Hz, 2H), 7.48 (t, J = 7.3 Hz, 1H), (m, 4H), 6.89 (d, J = Hz, 2H), 6.17 (br s, 1H), 5.45 (s, 1H), 5.23 (s, 1H), 4.52 (d, J = 5.5 Hz, 2H), 3.81 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 167.3, 159.4, 143.4, 134.3, 131.3,.6, 128.4, 127.1, 126.8, 113.8, 112.2, 55.1, S8
9 43.7; HRMS (ESI): calculated for [C 17 H a] + requires , found Me 1k H -(2-(3-methoxyphenyl)allyl)benzamide (1k) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) (m, 2H), 7.48 (t, J = 7.4 Hz, 1H), 7. (t, J = 7.6 Hz, 2H), (m, 1H), 7.7 (d, J = 7.7 Hz, 1H), 7.2 (s, 1H), (m, 1H), 6.23 (br s, 1H), 5.52 (s, 1H), 5.32 (s, 1H), 4.53 (d, J = 5.5 Hz, 2H), 3.81 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 167.3, 159.6, 144., 139.8, 134.3, 131.4, 129.4, 128.4, 126.8, 118.4, 113.8, 11, 111.7, 55.1, 4; HRMS (ESI): calculated for [C 17 H a] + requires , found n H -(2-(naphthalen-2-yl)allyl)benzamide (1n) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.92 (s, 1H), (m, 3H), 7.71 (d, J = 8.2 Hz, 2H), 7.64 (d, J = Hz, 1H), (m, 3H), 7.38 (t, J = Hz, 2H), 6.26 (br s, 1H), 5.67 (s, 1H), 5.43 (s, 1H), 4.66 (d, J = 5.4 Hz, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 167.4, 143.8, 135.5, 134.2, 133.2, 132.9, 131.3, 128.4, 128.2, 128., 127.4, 126.9, 126.2, 126.1, 124.8, 124.1, 114.2, 43.6; HRMS (ESI): calculated for [C H 17 +a] + requires 31.12, found q H -(3-phenylbut-3-en-1-yl)benzamide (1q) 2 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.65 (d, J = 8. Hz, 2H), (m, 3H), 7. (t, J = 7.6 Hz, 2H), 7.36 (t, J = 7.6 Hz, 2H), 7.31 (d, J = 7.2 Hz, 1H), 6.16 (br s, 1H), 5.43 (s, 1H), 5.19 (s, 1H), 9 (q, J = 6.3 Hz, 2H), 2.86 (t, J = 6.6 Hz, 2H); 13 C MR ( MHz, CDCl 3 ) δ (ppm) 16, 145.4,., 134.4, 131.3, 12, 128.4, 127.7, 126.7, 126., 114.3, 38.7, 34.8; HRMS (ESI): calculated for [C 17 H 17 +a] + requires , found Cl 4c H -(4-chloro-2-(1-phenylvinyl)phenyl)benzamide (4c) 3 : 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.47 (d, J = 8.8 Hz, 1H), 7.73 (br s, 1H), 7.44 (t, J = 7.4 Hz, 1H), (m, 6H), 7.34 (d, J = 2.4 Hz, 1H), 7.3 (t, J = 7.8 Hz, 2H), 7.23 (d, J = 8. Hz, 2H), 5.93 (s, 1H), 5.45 (s, 1H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 164.9, 145.2, 138.2, 134.4, 134.1, 133.1, 131.7,.2, 129.2, 129., 128.8, 12, 126.7, 126.6, 122.2, 11, 19.7; HRMS (ESI): calculated for [C 21 H 16 Cl+a] + requires , found General Procedures and Data of Products Conditions A: To a 1 ml schlenk tube equipped with a magnetic stir bar were added substrate 1 or 4 (.3 mmol, 1. equiv), Umemoto s reagent 2 (.33 mmol, 1.1 equiv), Ru(bpy) 3 (PF 6 ) 2 (.15 mmol,.5 equiv), ahc 3 (.6 mmol, 2. equiv) and dry CH 3 C (3. ml) under Ar. The resulting mixture was degassed via freeze-pump-thaw procedure (3 times). Then the reaction mixture was stirred under irradiation with the 3 W blue LEDs. The reaction was monitored via TLC (petroleum ether : ethyl acetate). Upon consumption of the starting materials, the solvent was evaporated under reduced pressure, the residue was purified by flash chromatography on silica gel (petroleum ether : ethyl acetate = 4:1) to give the desired product 3 S9
10 or 5. Conditions B: To a 1 ml schlenk tube equipped with a magnetic stir bar were added substrate 1 or 4 (.3 mmol, 1. equiv), BrCH(C 2 Et) 2 2b (.6 mmol 2. equiv), Ru(bpy) 3 Cl. 2 6H 2 (.3 mmol,.1 equiv), 4-methoxy-,-diphenylaniline (.6 mmol, 2. equiv), 4 Å MS (1 mg), a 2 HP 4 (.6 mmol, 2. equiv) and dry CH 3 C (3. ml) under Ar. The resulting mixture was degassed via freeze-pump-thaw procedure (3 times). Then the reaction mixture was stirred under irradiation with the 3 W blue LEDs. The reaction was monitored via TLC (petroleum ether : ethyl acetate). Upon consumption of the starting materials, the solvent was evaporated under reduced pressure, the residue was purified by flash chromatography on silica gel (petroleum ether : ethyl acetate = 5:1) to give the desired product 3 or 5. 3a 2,5-Diphenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3a): Colorless oil, 88% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) (d, J = 7.3 Hz, 2H), 3 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), (m, 4H), (m, 1H), 4.39 (d, J = 14.8 Hz, 1H), 4.23 (d, J = 14.9 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.9, 14, 131.7, 128.7, 12, 128.2, 127.9, 127.3, (q, J = Hz) 124.3, 84.6, 68.2, 44.2 (q, J = 26.9 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3438, 365, 2938, 1655, 145, 1377, 1349, 1262, 1133, 184, 696 cm -1 ; HRMS (ESI): calculated for [C 17 H 14 F 3 +a] + requires 328.9, found b Me 2-(4-Methoxyphenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3b): Colorless oil, 91% yield. 1 H MR ( MHz, CDCl 3 ) δ (ppm) 7.99 (d, J = 8.6 Hz, 2H), 7.38 (m, 4H), 7.31 (m, 1H), 6.96 (d, J = 8.6 Hz, 2H), 4.35 (d, J = 14.7 Hz, 1H), 4.18 (d, J = 14.7 Hz, 1H), 3.85 (s, 3H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.7, 162.3, 142.6,., 128.6, 127.8, (q, J = Hz), 124.3, 119.7, 113.8, 84.4, 68.2, 55.3, 44.1 (q, J = 27.3 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) -69 (s, 3F); IR (in KBr): 3441, 2936, 1654, 169, 1514, 135, 1259, 1169, 1133, 178, 13, 913, 841, 744, 72 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 2 +a] + requires , found c Me 5-enyl-2-(p-tolyl)-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3c): White solid, 89% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.94 (d, J = 8.1 Hz, 2H), (m, 4H), (m, 1H), (m, 2H), 4.36 (d, J = 14.7 Hz, 1H), 4. (d, J = 14.7 Hz, 1H), (m, 2H), 2.41 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 163., 142.6, 142.1, 129.2, 128.6, 128.2, 127.9, (q, J = Hz) 124.5, 124.3, 84.5, 68.1, 44.1 (q, J = 27.1 Hz), 2; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3425, 2927, 1654, 1377, 1349, 1262, 1133, 179, 913, 745, 676 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 +a] + requires , found d Br 2-(4-Bromophenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole(3d): Colorless S1
11 oil, 95% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.91 (d, J = Hz, 2H), 7.6 (d, J = Hz, 2H), (m, 4H), (m, 1H), 4.38 (d, J = 14.9, 1H), 4.21 (d, J = 14.9 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162., 142.3, 131.7, 129.7, 128.7, 128., 126.4, 126.2, (q, J = Hz), 124.2, 84.9, 68.1,44.1 (q, J = 2 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3424, 2928, 1656, 1593, 1488, 1398, 1377, 1348, 1262, 1134, 179, 111, 837, 727, 73 cm -1 ; HRMS (ESI): calculated for [C 17 H 13 BrF 3 +H] + requires 384.5, found (4-itrophenyl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3e): White Solid, 69% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.32 (d, J = 8.4 Hz, 3e 2H), 8.22 (d, J = Hz, 2H), (m, 4H), 7.35 (t, J = 6.8 Hz, 1H), 4.47 (d, J = 15.5 Hz, 1H), 4.3 (d, J = 15.4 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 161., 149.6, 142.1, 133., 129.2, 128.9, 128.2, (q, J = Hz), 124.1, 123.7, 85.5, 68.1, 44.2 (q, J = 27.2 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3438, 2973, 1655, 163, 161, 1526, 1378, 1343, 1261, 1133, 181, 143, 911, 867, 742, 73 cm -1 ; HRMS (ESI): calculated for [C 17 H 13 F H] + requires , found f 2-Mesityl-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3f): Colorless oil, 75% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) (m, 4H), 7.33 (s, 1H), 6.9 (s, 2H), 4.42 (d, J = 14.6 Hz, 1H), 4.35 (d, J = 14.7 Hz, 1H), (m, 2H), 2.3 (s, 3H), 2.29 (s, 6H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 163.3, 14, 13, 137., 128.6, 128.3, 127.9, 125.5, (q, J = Hz) 124.6, 84.2, 68.1, 45. (q, J = 27.1 Hz), 21.1, 19.7; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3425, 2925, 167, 1376, 126, 1131, 162, 136, 744, 73 cm -1, HRMS (ESI): calculated for [C H F 3 +a] + requires , found g 2-(Furan-2-yl)-5-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3g): Colorless oil, 45% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.6 (d, J =.9 Hz, 1H), (m, 4H), (m, 1H), 7.1 (d, J = 3.4 Hz, 1H), 4 (dd, J = 3.4 Hz, J = 1.8 Hz, 1H), 4.39 (d, J = 14.9 Hz, 1H), 4.23 (d, J = 14.9 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 155.2, 145.6, 14, 142., 128.7, 128.1, (q, J = Hz), 124.3, 114.9, 111.6, 85., 67.7, 44. (q, J = 27. Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3435, 293, 1678, 1483, 1378, 1261, 1, 193, 75, 71 cm -1 ; HRMS (ESI): calculated for [C 15 H 12 F 3 2 +a] + requires , found h 5-enyl-2-(pyridin-2-yl)-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3h): Colorless oil, 94% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 9.26 (s, 1H), (m, 1H), 8.31 (d, J = 7.9 Hz, 1H), (m, 5H), (m, 1H), 4.44 (d, J = 15. Hz, 1H), 4.26 (d, J = 15.1 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 16.8, 152.2, 149.3, 142.2, 135.5, 128.7, 128.1, (q, J = 2.4 Hz), 124.1, 123.4, 123.3, 85., 67.8, 44.1 (q, J = 27. Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3441, 2925, 1659, 1592, 1379, 1352, 1261, 1129, 183, 121, 75 cm -1 ; HRMS S11
12 (ESI): calculated for [C 16 H 13 F 3 2 +H] + requires , found enyl-5-(p-tolyl)-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3i): Colorless oil, 94% Me 3i yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.8 (d, J = 7.3 Hz, 2H), 2 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.7 Hz, 2H), 7.31 (d, J = 7.9 Hz, 2H), 7. (d, J = 7.9 Hz, 2H), 4.38 (d, J = 14.8 Hz, 1H), 4.22 (d, J = 14.8 Hz, 1H), (m, 2H), 2.35 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.8, 139.6, 137.6, 131.6, 129.3, 128.4, 128.2, 127.4, (q, J = Hz), 124.2, 84.6, 68.1,44.1 (q, J = 27.2 Hz),.9; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) -67 (s, 3F); IR (in KBr): 32, 2975, 2928, 1655, 1451, 1377, 135, 1263, 1134, 186, 127, 911, 741, 696 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 +a] + requires , found (4-Methoxyphenyl)-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3j): Me 3j Colorless oil, 81% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.4 (d, J = 7.4 Hz, 2H), 3 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.33 (d, J = 8.7 Hz, 2H), 6.91 (d, J =8.8 Hz, 2H), 4.36 (d, J = 14.7 Hz, 1H), 4.21 (d, J = 14.8 Hz, 1H), 3.81 (s, 3H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.8, 159.2, 134.5, 131.6, 128.4, 128.2, 127.4, 125.6, (q, J = Hz), 114., 84.5, 68., 55.2, 44.2 (q, J = 27. Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3431, 2968, 1655, 1614, 1515, 1377, 1349, 1259, 1179, 1134, 184, 13, 912, 744, 696 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 2 +a] + requires , found Me 5-(3-Methoxyphenyl)-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3k): Colorless oil, 92% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.4 (d, J = 7.8 Hz, 2H), 3 3k (t, J = 7.3 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.32 (t, J = 7.9 Hz, 1H), (m, 2H), 6.85 (d, J = 8.3 Hz, 1H), 4.37 (d, J = 14.9 Hz, 1H), 4.21 (d, J = 14.9 Hz, 1H), 3.82 (s, 3H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.8, 159.8, 144.2, 131.6, 129.8, 128.4, 128.2, 127.3, (q, J = Hz), 116.6, 112.6, 11.8, 84.5, 68.2, 55.2, 44.1 (q, J = 27. Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 34, 2942, 1656, 167, 1585, 1491, 1377, 1349, 1264, 1231, 1129, 185, 158, 126, 911, 745, 695 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 2 +a] + requires , found (4-Chlorophenyl)-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3l): Colorless Cl oil, 94% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.3 (d, J = 7.9 Hz, 2H), 4 (t, J = 7.4 3l Hz, 1H), 7.47 (t, J = 7.7 Hz, 2H), (m, 4H), 4.37 (d, J = 14.8 Hz, 1H), 4.18 (d, J = 14.8 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.7,.9, 133.8, 131.8, 128.9, 12, 128.2, 127., 125.8, (q, J = Hz), 84.2, 68.3, 44.1 (q, J = 27.2 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) -65 (s, 3F); IR (in KBr): 3446, 2937, 1656, 1494, 1377, 1349, 1261, 1133, 186, 165, 122, 99, 744, 695 cm -1 ; HRMS (ESI): calculated for [C 17 H 13 ClF 3 +H] + requires 3.75, found (Furan-2-yl)-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3m): Colorless oil, 3m S12
13 48% yield. 1 H MR ( MHz, CDCl 3 ) δ (ppm) 7.96 (d, J = 7.2 Hz, 2H), (m, 4H), 6.43 (d, J = 3.3 Hz, 1H), 6.37 (m, 1H), 4.43 (d, J = 15.3 Hz, 1H), 4.28 (d, J = 15.3 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.6, 152.2, 143.4, 131.7, 128.4, 128.2, 127., (q, J = 276. Hz), 1, 17.4,.3, 64., 41. (q, J = 27.8 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3434, 2948, 1655, 8, 1371, 1348, 126, 1132, 192, 126, 913, 743, 696 cm -1 ; HRMS (ESI): calculated for [C 15 H 12 F 3 2 +H] + requires , found n 5-(aphthalen-2-yl)-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3n): Colorless oil, 71% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.11 (d, J = 7.1 Hz, 2H), (m, 2H), (m, 2H), 2 (t, J = 7.4 Hz, 1H), 7.44 (m, 4H), 7.42 (d, J = 8.6 Hz, 1H), 4.43 (d, J = 14.9 Hz, 1H), 4.29 (d, J = 14.8 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.9, 139.6, 133., 132.7, 131.7, 128.8, 12, 128.3, 128.2, 127.6, 127.3, 126.6, 126.4, (q, J = Hz), 123.1, 122.3, 84.8, 68.2, 44.1 (q, J = 27.4 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) - 65 (s, 3F); IR (in KBr): 3444, 361, 2932, 1655, 1377, 1264, 1138, 184, 91, 747, 695, 477 cm -1 ; HRMS (ESI): calculated for [C 21 H 16 F 3 +a] + requires , found o 5-Methyl-2-phenyl-5-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole (3o): Colorless oil, 35% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.93 (d, J = 7.2 Hz, 2H), 7.49 (t, J = 7.2 Hz, 1H), 7.42 (t, J = Hz, 2H), 4.1 (d, J = 14.8 Hz, 1H), 3.85 (d, J = 14.9 Hz, 1H), (m, 2H), 1.6 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.8, 13, 128.3, 128.1, 12, (q, J = 276. Hz) 81.8, 66.3, 43.1 (q, J = 27.4 Hz), 25.3; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) -62. (s, 3F); IR (in KBr): 343, 2976, 2877, 1651, 1452, 1378, 135, 127, 12, 1167, 118, 185, 162, 126, 911, 779, 741, 695 cm -1 ; HRMS (ESI): calculated for [C 12 H 12 F 3 +a] + requires , found p 2,5-Diphenyl-5-(1,1,1-trifluoropropan-2-yl)-4,5-dihydrooxazole (3p): Colorless oil, 7% yield, dr = 1.1:1. 1 H MR ( MHz, CDCl 3 ) δ (ppm) major + minor: 1 H MR ( MHz, CDCl 3 ) δ (ppm) 8.3 (m, 4H), (m, 2H), (m, 6H), (m, 6H), (m, 2H), 4.6 (d, J = 15.2 Hz, 1H), 4.49 (d, J = 15.2 Hz, 1H), 4.35 (d, J = 15.1 Hz, 1H), 4.28 (d, J = 15.1 Hz, 1H), (m, 2H), 1.28 (d, J = 7. Hz, 3H), 1. (d, J = 7.1 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 162.9, 162.6, 14, 141.9, 131.6, 13, 128.6, 12, 128.4, 128.2, 128.1, 127.9, 127.8, 127.4, 127.2, 127. (q, J = 267. Hz), (q, J = 264. Hz), 125.2, 125., 87.8, 8, 67.1, 65.7, 4 (q, J = 24. Hz), 46.7 (q, J = 24.5 Hz), 1.4, 9.1; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F), (s, 3F); IR (in KBr): 3424, 2973, 1658, 1451, 1348, 1267, 1175, 11, 184, 147, 913, 745, 696 cm -1 ; calculated for [C 18 H 16 F 3 +H] + requires , found q 2,6-Diphenyl-6-(2,2,2-trifluoroethyl)-5,6-dihydro-4H-1,3-oxazine (3q): Colorless oil, 78% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.11 (m, 2H), (m, 3H), (m, 2H), (m, 3H), (m, 1H), (m, 1H), (m, 2H), 2.39 S13
14 2.35 (m, 1H), (m, 1H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 154.3, 141.1, 133.1,.8, 128.8, 128.2, 128., 127., 125. (q, J = Hz), 124.4, 77.4, 45.8 (q, J = 26.3 Hz),., 31.3; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) -6.7 (s, 3F); IR (in KBr): 3432, 364, 2931, 1659, 1448, 1379, 1262, 1126, 169, 911, 699 cm -1 ; HRMS (ESI): calculated for [C 18 H 16 F 3 +a] + requires , found Et 2 C C 2 Et 3r Diethyl 2-((2,5-diphenyl-4,5-dihydrooxazol-5-yl)methyl)malonate (3r): Brown oil, 82% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.99 (d, J = 7.7 Hz, 2H), 1 (d, J = 7.1 Hz, 1H), 7.45 (t, J = Hz, 2H), (m, 4H), 7.3 (d, J = 5.9 Hz, 1H), 4.27 (d, J = 14.8 Hz, 1H), 4.17 (d, J = 15. Hz, 1H), (m, 3H), (m, 1H), 3.43 (t, J = 6.3 Hz, 1H), 2.78 (d, J = 6.4 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H), 1.8 (t, J = 7.1 Hz, 3H), 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 169., 168.9, 162.6, 142.9, 131.4, 128.6, 128.3, 128.1, 127.6, 12, 124.7, 87.8, 6, 6 (overlap), 48.2, 39.8, 13.8, 13.7; IR (in KBr): 3429, 2977, 2932, 1733, 1653, 1633, 1448, 137, 1268, 1151, 15, 126, 778, 697 cm -1 ; HRMS (ESI): calculated for [C 23 H a] + requires , found Me Et 2 C C 2 Et 3s Diethyl 2-((2-phenyl-5-(p-tolyl)-4,5-dihydrooxazol-5-yl)methyl)malonate (3s): Brown oil, 85% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.98 (d, J = 7.6 Hz, 2H), (t, J = Hz, 1H), 7.44 (t, J = 7.6 Hz, 2H), 7.27 (d, J = 5.5 Hz, 2H), 7.18 (d, J = 7.9 Hz, 2H), 4.23 (d, J = 14.6 Hz, 1H), (m, 2H), (m, 2H), (m, 1H), 3.41 (t, J = 6.4 Hz, 1H), 2.75 (d, J = 6.4 Hz, 2H), 2.34 (s, 3H), 1.16 (t, J = 7.1 Hz, 3H), 1.9 (t, J = 7.1 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 169., 168.8, 162.6, 139.8, 137.2, 131.3, 129.2, 128.2, 128., 12, 124.5, 87.8, 68.4, 61.4 (overlap), 48.1, 39.7,.8, 13.7, 13.6; IR (in KBr): 2982, 2933, 2871, 1733, 1653, 15, 1514, 1449, 1347, 1269, 1236, 1152, 199, 153, 125, 818, 696 cm -1 ; HRMS (ESI): calculated for [C 24 H a] + requires , found Et 2 C C 2 Et Diethyl 2-((5-(naphthalen-2-yl)-2-phenyl-4,5-dihydrooxazol-5-yl)methyl)malonate (3t): 3t Brown oil, 77% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.4 (d, J = Hz, 2H), (m, 2H), 7.84 (t, J = 8.1 Hz, 2H), 4 (t, J = 7.3 Hz, 1H), (m, 4H), 7.42 (d, J = 8.6 Hz, 1H), 4.34 (d, J = 14.7 Hz, 1H), 4.26 (d, J = 14.7 Hz, 1H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), 3.47 (t, J = 6.3 Hz, 1H), (m, 2H), 1.17 (t, J = 7.1 Hz, 3H),.98 (t, J = 7.1 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 169., 168.8, 162.7, 139.8, 132.8, 13, 13, 128.7, 128.3, 128.1, 128.1, 12, 126.4, 126.2, 12, 122.7, 88., 68.3, 6, 61.4, 48.2, 39.6, 13.8, 1; IR (in KBr): 3441, 2981, 2852, 1732, 1653, 1448, 1334, 1269, 1151, 153, 125, 859, 778, 696 cm -1 ; HRMS (ESI): calculated for [C 27 H a] + requires , found Et 2 C C 2 Et Diethyl 2-((5-phenyl-2-(pyridin-2-yl)-4,5-dihydrooxazol-5-yl)methyl)malonate (3u): 3u Brown oil, 42% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 9.17 (s, 1H), 8.74 (d, J = 4.8 Hz, 1H), 8.26 (d, J = 8. Hz, 1H), (m, 5H), 7.31 (t, J = 6.7 Hz, 1H), 4.28 (d, J = 15. Hz, 1H), (m, 3H), (m, 1H), (m, 1H), 3.41 (t, J = 6.4 Hz, 1H), 2.79 (d, J = 6.4 S14
15 Hz, 2H), 1. (t, J = 7.1 Hz, 3H), 1.11 (t, J = 7.1 Hz, 3H); 13 C MR ( MHz, CDCl 3 ) δ (ppm) 169., 168.7, 16.6, 152.1, 149.2, 142.3, 135.5, 128.7, 127.8, 124.6, 123.6, 123.2, 88.4, 68.4, 61.6, 61.6, 48., 39.7, 13.8, 13.7; IR (in KBr): 345, 2982, 2934, 1732, 1657, 1592, 1447, 1332, 1272, 1236, 1153, 181, 123, 745, 76 cm -1 ; HRMS (ESI): calculated for [C 22 H a] + requires , found C 2 Et Et 2 C 3v Diethyl 2-(2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-6-yl)malonate (3v): Brown oil, 55% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.1 (d, J = 7.3 Hz, 2H), 7.47 (t, J = 7.3 Hz, 1H), 7.42 (t, J = 7.4 Hz, 2H), (m, 2H), 7.28 (d, J = 8. Hz, 3H), (m, 2H), (m, 1H), (m, 1H), (m, 1H), 3.47 (t, J = 6.2 Hz, 1H), (m, 1H), 2.72 (d, J = 6.2 Hz, 2H), (m, 1H), 2.15 (m, 1H), 1. (t, J = 7.1 Hz, 3H), 1.12 (t, J = 7.1 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 169.3, 169., 154.3, 141.6, 133.6,.5, 128.7, 128., 127.6, 127., 124.8,., 6 (overlap), 47.3,.7,.5, 32.4, 13.9, 13.8; IR (in KBr): 3435, 2981, 2935, 1732, 1658, 1493, 1447, 137, 1349, 1279, 1, 199, 167, 129, 765, 699 cm -1 ; HRMS (ESI): calculated for [C 24 H a] + requires , found a 4-Methyl-2-phenyl-4-(2,2,2-trifluoroethyl)-4H-benzo[d][1,3]oxazine (5a): White Solid, 74% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.17 (d, J = 7.3 Hz, 2H), 7.49 (t, J = 7.3 Hz, 1H), 7.44 (t, J = Hz, 2H), (m, 2H), (m, 1H), 7.11 (d, J = 7.6 Hz, 1H), (m, 1H), (m, 1H), 1.9 (s, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 155.6, 138.3, 132.2, 13, 129.3, 128.2, 128., 126.9, 125.6, 125.9, (q, J = Hz), 12, 76.6, 43.6 (q, J = 27.1 Hz), 26.3; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3443, 1628, 16, 1574, 1485, 1452, 137, 1323, 1258, 1154, 1133, 166, 189, 913, 764, 747, 696 cm -1 ; HRMS (ESI): calculated for [C 17 H 14 F 3 +a] + requires 328.9, found b 2,4-Diphenyl-4-(2,2,2-trifluoroethyl)-4H-benzo[d][1,3]oxazine (5b): White Solid, 94% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.35 (d, J = 8. Hz, 2H), 9 5 (m, 1H), 3 (t, J = 7.2 Hz, 2H), (m, 4H), 7.33 (t, J = 7.4 Hz, 2H), (m, 3H), (m, 2H); 13 C MR ( MHz, CDCl 3 ) δ (ppm) 155.4, 14, 138.6, 131.9, 131.6, 129.4, 12, 128.4, 128.3, 127.9, 12, 126.2, 125.8, 125.4, (q, J = Hz), 124.2,., 43.3 (q, J = 27.2 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3442, 1628, 1598, 1574, 1485, 1453, 1375, 1321, 1264, 1129, 182, 912, 764, 745, 697 cm -1 ; HRMS (ESI): calculated for [C 22 H 16 F 3 +H] + requires , found Cl 5c 6-Chloro-2,4-diphenyl-4-(2,2,2-trifluoroethyl)-4H-benzo[d][1,3]oxazine (5c): White Solid, 98% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.23 (d, J = 7.4 Hz, 2H), 6 (m, 1H), 7.42 (m, 2H), (m, 7H), 7.17 (d, J = 6.2 Hz, 1H), (m, 2H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 155.6,.9, 137.3, 131.8, 131.6, 129.6, 128.7, 128.6, 128.4, 128., 127.7, 127.2, 125.3, (q, J = 27 Hz), 124.3, 79.8, 43.3 (q, J = 27.6 Hz); 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3446, 365, 1626, 1576, 1474, 1374, 1315, 126, 1133, 182, 911, 833, 743, S15
16 695 cm -1 ; HRMS (ESI): calculated for [C 22 H 15 ClF 3 +H] + requires 2.867, found d 2-(Tert-butyl)-4-phenyl-4-(2,2,2-trifluoroethyl)-4H-benzo[d][1,3]oxazine (5d): Colorless oil, 88% yield. 1 H MR (6 MHz, CDCl 3 ) δ (ppm) (m, 4H), (m, 2H), 7.24 (d, J = 7.8 Hz, 1H), 7. (t, J = Hz, 1H), 7.8 (d, J = 7.6 Hz, 1H), (m, 2H), 1.24 (s, 9H); 13 C MR ( MHz, CDCl 3 ) δ (ppm) 166.1, 142.9, 138.6, 129.2, 12, 128.3, 125.9, 125.8, 125.6, 124.9, (q, J = Hz), 124., 79.3, 4 (q, J = 27. Hz ), 37.2, 2; 19 F MR (376 MHz, CDCl 3 ) δ (ppm) (s, 3F); IR (in KBr): 3423, 2975, 1638, 161, 1485, 1456, 1372, 6, 1261, 1129, 914, 768, 746, 698 cm -1 ; HRMS (ESI): calculated for [C H F 3 +a] + requires , found C 2 Et Et 2 C 5e Diethyl 2-((2,4-diphenyl-4H-benzo[d][1,3]oxazin-4-yl)methyl)malonate (5e):White solid, 56% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 8.18 (d, J = 7.7 Hz, 2H), (t, J = 7.1 Hz, 1H), 7.45 (t, J = 7.6 Hz, 2H), (m, 1H), 7.35 (d, J = 4.6 Hz, 2H), (m, 3H), (m, 3H), (m, 3H), (m, 1H), (m, 1H), (m, 1H), (m, 1H), 1. (t, J = 7.1 Hz, 3H), (t, J = 7.1 Hz, 3H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 16, 169.1, 155.8, 142.8, 139.8, 132.1, 13, 129.3, 128.3, 128.2, 127.8, 126.6, 126.2, 125.9, 125.8, 125.4, 124.2, 83.4, 61.7, 61.4, 48.8, 39.1, 13.8, 13.7; IR (in KBr): 345, 363, 2982, 1732, 1626, 1598, 1573, 14, 1451, 137, 1319, 1262, 1181, 1152, 189, 148, 913, 767, 745, 697 cm -1 ; HRMS (ESI): calculated for [C 28 H a] + requires , found C 2 Et Et 2 C 5f Diethyl 2-((2-(tert-butyl)-4-phenyl-4H-benzo[d][1,3]oxazin-4-yl)methyl)malonate (5f): White solid, 55% yield. M.P.: o C; 1 H MR (6 MHz, CDCl 3 ) δ (ppm) 7.34 (t, J = 7.3 Hz, 1H), (m, 4H), (m, 4H), (m, 1H), (m, 3H), (m, 1H), (m, 1H), 3.1 (m, 1H), 1.24 (t, J = 7.1 Hz, 3H), 1. (t, J = 7.1 Hz, 3H), 1.14 (s, 9H); 13 C MR (1 MHz, CDCl 3 ) δ (ppm) 169.2, 167.2, 143.,.2, 129.2, 128.2, 128., 126.3, 126.2, 126.1, 125.4, 124.7, 124.7, 82.8, 61.7, 61.4, 48.8, 38.4, 37.2, 27.4, 13.9, 13.8; IR (in KBr): 3452, 2979, 2933, 1734, 1633, 16,15, 1484, 1454, 1369, 1265, 1185, 1148, 13, 4, 77, 7, 588 cm -1 ; HRMS (ESI): calculated for [C 26 H a] + requires 44, found 48. S16
17 8.Copies of 1 H MR, 13 C MR and 19 F MR Spectra H 1f H 1f S17
18 S H 1g H 1g
19 S H Me 1j H Me 1j
20 S H 1k Me H 1k Me
21 S H 1n H 1n
22 S H 1q H 1q
23 S H Cl 4c H Cl 4c
24 S a 3a
25 S a Me 3b
26 S Me 3b Me 3b
27 S Me 3c Me 3c
28 S Me 3c Br 3d
29 S Br 3d Br 3d
30 S e 2 3e
31 S e 3f
32 S f 3f
33 S g 3g
34 S g 3h
35 S h
36 S Me 3i Me 3i
37 S Me 3i Me 3j
38 S Me 3j Me 3j
39 S Me 3k Me 3k
40 S Me 3k Cl 3l
41 S Cl 3l Cl 3l
42 S m 3m
43 S m 3n
44 S n 3n
45 S o 3o
46 S o 3p
47 S p 3p
48 S q 3q
49 S q Et 2 C C 2 Et 3r
50 Et 2 C C 2 Et 3r Me Et 2 C C 2 Et 3s S5
51 S Et 2 C C 2 Et Me 3s Et 2 C C 2 Et 3t
52 Et 2 C C 2 Et 3t Et 2 C C 2 Et 3u S52
53 Et 2 C C 2 Et 3u S53
54 S a
55 S a 5a
56 S b 5b
57 S b Cl 5c
58 S Cl 5c Cl 5c
59 S d 5d
60 5d C 2 Et Et 2 C 5e S6
61 C 2 Et Et 2 C 5e C 2 Et Et 2 C 5f S61
62 S C 2 Et Et 2 C 5f
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