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1 Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo Jiang, a Xiaofei Zhang b and Chunhao Yang* b a Nano Science and Technology Institute, University of Science and Technology of China, Suzhou, China. b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai , China. Supporting Information Lists of Contents Experimental Section...2 Characterization data...4 References H NMR, 19 F NMR and 13 C NMR and spectra
2 Experimental Section General Experimental Information Unless otherwise noted, all solvents and other reagents are commercially available and used without further purification. All reagents were weighed and handled in air at room temperature. NMR spectra were recorded on Brucker Avance 300 NMR spectrometer, Brucker Avance III 400 NMR spectrometer or Brucker Avance III 500 NMR spectrometer. Chemical shifts were reported in parts per million (ppm, δ). Proton coupling patterns are described as singlet (s), doublet (d), triplet (t), quartet (q) and multipet (m). Tetramethylsilane (TMS) was used as internal standard ( 1 H NMR: TMS at 0.00 ppm; CHCl 3 at 7.26 ppm; 13 C NMR: CDCl 3 at ppm, DMS at ppm). Low and high-resolution mass spectra (LRMS and HRMS) were recorded on a Finnigan/MAT-95 (EI), Finnigan LCQ/DECA or Micromass Ultra Q-TF (ESI) spectrometer. Melting points were measured by Büchi 510 melting point apparatus without further corrected. General experimental procedure of α-cf 3 aryl ketones R H B H + C + ICH 2 CF 3 Pd(PPh 3 ) 4, Johnphos K 2 C 3, CF 3 Ph/H 2 R CF To a 25 ml of two-neck bottle were added boronic acid (0.5mmol, 1.0 equiv), Pd(PPh 3 ) 4 (5 mol%), 2-(di-tert-butylphosphino)biphenyl (10 mol%), K 2 C 3 (0.5mmol, 1.0 equiv) with a condenser under a C balloon. The mixture was then evacuated and backfilled with C (5 times). And then 1,1,1-trifluoro-2-iodoethane (1.6 mmol, 3.2 equiv), and Trifluorotoluene (3 ml), H 2 (1 ml) were added subsequently. The bottle was put into a preheated oil bath (70 o C). After stirring for 12 h, the reaction mixture was cooled to room temperature. Then, the reaction mixture was extracted with EtAc/ H 2, and the organic phase was washed with brine, dried over anhydrous Na 2 S 4, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give product (PE:EA=200:1~50:1). Experimental procedure of 2a in gram scale To a 100 ml of two-neck bottle were added [1,1'-biphenyl]-4-ylboronic acid (1 g), Pd(PPh 3 ) 4 (290 mg), 2-(di-tert-butylphosphino)biphenyl (150 mg) and K 2 C 3 (700 mg). Then, the reaction was conducted with a condenser under a balloon of C. The mixture was then evacuated and backfilled with C (5 times). And then 1,1,1-trifluoro- 2
3 2-iodoethane (1.5 ml), and Trifluorotoluene (15 ml), H 2 (5 ml) were added subsequently. The bottle was put into a preheated oil bath (70 o C). After stirring for 12 h, the reaction mixture was cooled to room temperature. Then, the reaction mixture was extracted with EtAc/ H 2, and the organic phase was washed with brine, dried over anhydrous Na 2 S 4, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give product 2a (760 mg, 77%). (PE:EA=200:1). 3
4 Characterization data 1-(Biphenyl-4-yl)-3,3,3-trifluoropropan-1-one (2a) (Lit. 1 ) F 3 C Ph White solid (79%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), (m, 2H), (m, 3H), 3.83 (q, J = 10.0 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , , (q, J = Hz), (q, J = 28.2 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). Q- TF (ESI) m/z [M-H] - calculated for C 15 H 10 F 3, ; found, (Biphenyl-3-yl)-3,3,3-trifluoropropan-1-one (2b) (Lit. 2 ) F 3 C Ph Colorless oil (68%). 1 H NMR (300 MHz, CDCl 3 ) δ 8.14 (s, 1H), 7.87 (dd, J = 13.6, 7.8 Hz, 2H), (m, 3H), (m, J = 22.7, 7.1 Hz, 3H), 3.85 (q, J = 10.0 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , , , , δ (q, J = Hz), (q, J = 28.3 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). Q-TF (ESI) m/z [M-H] - calculated for C 15 H 10 F 3, ; found, ,3,3-Trifluoro-1-p-tolylpropan-1-one (2c) (Lit. 1 ) CF 3 CH 3 Colorless oil (50%). 1 H NMR (300 MHz, CDCl 3 ) δ 7.84 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 3.77 (q, J = 10.0 Hz, 2H), 2.44 (s, 3H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , δ (q, J = Hz), (q, J = 28.1 Hz), F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). HRMS (EI) m/z [M] + calculated for C 10 H 9 F 3, ; found, (4-Tert-butylphenyl)-3,3,3-trifluoropropan-1-one (2d) (Lit. 4 ) CF 3 tbu Colorless oil (55%). 1 H NMR (300 MHz, CDCl 3 ) δ 7.88 (dd, J = 8.7, 2.0 Hz, 2H), 7.52 (dd, J = 8.6, 1.9 Hz, 2H), 3.77 (q, J = 10.1 Hz, 2H), 1.35 (s, 9H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , 4
5 126.05, (q, J = Hz), (q, J = 28.2 Hz), 35.41, F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). HRMS (EI) m/z [M] + calculated for C 13 H 15 F 3, ; found, ,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one (2e) (Lit. 1 ) F 3 C CH 3 White solid (66%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.92 (d, J = 8.9 Hz, 2H), 6.97 (d, J = 8.9 Hz, 2H), 3.89 (s, 3H), 3.75 (q, J = 10.1 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , (q, J = Hz), , 55.73, (q, J = 28.0 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). HRMS (EI) m/z [M] + calculated for C 10 H 9 2 F 3, ; found, ,3,3-Trifluoro-1-(4-(methylthio)phenyl)propan-1-one (2f) F 3 C SCH 3 White solid (48%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.84 (dd, J = 8.8, 2.0 Hz, 2H), 7.28 (dd, J = 6.9, 5.1 Hz, 2H), 3.75 (q, J = 10.0 Hz, 2H), 2.54 (s, 3H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , (q, J = Hz), (q, J = 28.2 Hz), F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). Q-TF (ESI) m/z [M+H] + calculated for C 10 H 10 F 3 S, ; found, ,3,3-Trifluoro-1-(4-phenoxyphenyl)propan-1-one (2g) (Lit. 2 ) F 3 C Ph White solid (78%). M.P o C. 1 H NMR (300 MHz, DMS) δ 8.02 (d, J = 8.9 Hz, 2H), (m, 2H), (m, 1H), (m, 2H), 7.07 (d, J = 8.9 Hz, 2H), 4.36 (q, J = 10.9 Hz, 2H). 13 C NMR (125 MHz, DMS) δ , , , , , , (q, J = Hz), , , , (q, J = 26.5 Hz). 19 F NMR (471 MHz, DMS) δ (t, J = 10.8 Hz). HRMS (EI) m/z [M] + calculated for C 15 H 11 2 F 3, ; found, (4-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2h) (Lit. 3 ) Bn F 3 C White solid (61%). M.P o C. 1 H NMR (500 MHz, CDCl 3 ) δ (m, 2H), (m, 4H), (m, 1H), 5
6 (m, 2H), 5.15 (s, 2H), 3.73 (q, J = 10.1 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , (q, J = Hz), , , 70.44, (q, J = 28.1 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). HRMS (EI) m/z [M] + calculated for C 16 H 13 F 3 2, ; found, (3-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2i) F 3 C Bn White solid (56%). M.P o C. 1 H NMR (300 MHz, DMS) δ (m, 2H), (m, 7H), 5.17 (s, 2H), 4.40 (q, J = 10.9 Hz, 2H). 13 C NMR (125 MHz, DMS) δ , , , , , , , , (q, J = Hz), , , , 69.51, δ (q, J = 26.5 Hz). 19 F NMR (471 MHz, DMS) δ (t, J = 10.8 Hz). Q-TF (ESI) m/z [M-H] - calculated for C 16 H 12 F 3 2, ; found, (2-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2j) F 3 C Bn White solid (40%). M.P o C. 1 H NMR (300 MHz, DMS) δ 7.71 (dd, J = 7.7, 1.5 Hz, 1H), (m, 3H), 7.37 (ddd, J = 29.0, 14.5, 7.6 Hz,4H), 7.09 (t, J = 7.5 Hz, 1H), 5.28 (s, 2H), 4.18 (q, J = 10.9 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , (q, J = Hz), , , 71.21, (q, J = 27.5 Hz). 19 F NMR (471 MHz, DMS) δ (t, J = 10.9 Hz). Q-TF (ESI) m/z [M-H] - calculated for C 16 H 12 F 3 2, ; found, (2-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2k) (Lit. 1 ) F 3 C Cl White solid (58%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.88 (d, J = 8.6 Hz, 2H), 7.49 (d, J = 8.7 Hz, 2H), 3.78 (q, J = 9.9 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , (q, J = Hz), (q, J = 28.4 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 9.9 Hz). HRMS (EI) m/z [M] + calculated for C 9 H 6 ClF 3, ; found,
7 3,3,3-Trifluoro-1-(4-(trifluoromethoxy)phenyl)propan-1-one (2l) F 3 C CF 3 Colorless solid (45%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.01 (d, J = 8.9 Hz, 2H), 7.34 (d, J = 8.1 Hz, 2H), 3.80 (q, J = 9.9 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , δ (q, J = Hz), , δ (q, J = Hz), δ (q, J = 28.6 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (s, 3F), (t, J = 9.8 Hz, 3F). HRMS (EI) m/z [M] + calculated for C 10 H 6 2 F 6, ; found, ,3,3-Trifluoro-1-(2-fluorobiphenyl-4-yl)propan-1-one (2m) F 3 C F Ph White solid (70%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), (m, 3H), 3.81 (q, J = 9.9 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , (d, J = Hz), (d, J = 6.4 Hz), (d, J = 13.7 Hz), , (d, J = 3.4 Hz), , , , , (d, J = 3.4 Hz), (q, J = Hz), (d, J = 24.6 Hz), (q, J = 28.5 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 9.9 Hz, 3F), (m, 1F). HRMS (EI) m/z [M] + calculated for C 15 H 10 F 4, ; found, (3,5-Dichlorophenyl)-3,3,3-trifluoropropan-1-one (2n) CF 3 Cl Cl Colorless solid (33%). M.P. 40 o C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.79 (d, J = 1.8 Hz, 1H), 7.63 (t, J = 1.8 Hz, 1H), 3.77 (q, J = 9.7 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , (q, J = Hz), (q, J = 28.9 Hz). 19 F NMR (565 MHz, CDCl 3 ) δ (t, J = 9.7 Hz). HRMS (EI) m/z [M] + calculated for C 9 H 5 Cl 2 F 3, ; found, ,3,3-Trifluoro-1-(naphthalen-2-yl)propan-1-one (2o) (Lit. 1 ) F 3 C 7
8 White solid (67%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.42 (s, 1H), (m, 4H), (m, 2H), 3.94 (q, J = 10.0 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , , , (q, J = Hz), , (q, J = 28.4 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 9.9 Hz). HRMS (EI) m/z [M] + calculated for C 13 H 9 F 3, ; found, ,3,3-Trifluoro-1-(7-methoxynaphthalen-2-yl)propan-1-one (2p) (Lit. 4 ) F 3 C CH 3 White solid (67%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.34 (s, 1H), 7.98 (dd, J = 8.7, 1.8 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.79 (d, J = 8.7 Hz, 1H), 7.23 (dd, J = 9.0, 2.5 Hz, 1H), 7.16 (d, J = 2.3 Hz, 1H), 3.96 (s, 3H), 3.90 (q, J = 20.2, 10.1 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , (q, J = Hz), , , 55.63, (q, J = 28.1 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). Q-TF (ESI) m/z [M+H] + calculated for C 14 H 12 F 3 2, ; found, ,3,3-Trifluoro-1-(4'-fluorobiphenyl-4-yl)propan-1-one (2q) F 3 C F White solid (61%). M.P o C. 1 H NMR (500 MHz, DMS) δ (m, 2H), (m, 4H), (m, 2H), 4.44 (q, J = 10.9 Hz, 2H). 19 F NMR (471 MHz, DMS) δ (t, J = 10.8 Hz, 3F), δ (m, 1F). 13 C NMR (125 MHz, DMS) δ , δ (d, J = Hz), , (d, J = 3.0 Hz), , , , , , (q, J = Hz), , , (q, J = 26.6 Hz). 19 F NMR (471 MHz, DMS) δ (t, J = 10.8 Hz, 3F), δ (m, 1F). HRMS (EI) m/z [M] + calculated for C 15 H 10 F 4, ; found, ,3,3-Trifluoro-1-(9-phenyl-9H-carbazol-3-yl)propan-1-one (2r) CF 3 N Ph White solid (60%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.75 (d, J = 1.4 Hz, 1H), (m, 1H), 8.01 (dd, J = 8.8, 1.8 Hz, 1H), (m, 2H), (m, 4H), (m, 3H), 3.93 (q, J = 10.1 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , , , 8
9 (q, J = Hz), , , , , , , , δ (q, J = 27.9 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). HRMS (EI) m/z [M] + calculated for C 21 H 14 NF 3, ; found, (Dibenzo[b,d]furan-4-yl)-3,3,3-trifluoropropan-1-one (2s) CF 3 White solid (73%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.20 (dd, J = 7.6, 1.3 Hz, 1H), 8.11 (dd, J = 7.8, 1.3 Hz, 1H), (m, 1H), 7.68 (d, J = 8.3 Hz, 1H), (m, 1H), (m, 2H), 4.26 (q, J = 10.0 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , δ (q, J = Hz), , , , , , δ (q, J = 27.9 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.0 Hz). HRMS (EI) m/z [M] + calculated for C 15 H 9 2 F 3, ; found, (Dibenzo[b,d]thiophen-4-yl)-3,3,3-trifluoropropan-1-one (2t) (Lit. 5 ) F 3 C S White solid (60%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.44 (d, J = 7.5 Hz, 1H), (m, 1H), (m, 2H), 7.62 (t, J = 7.7 Hz, 1H), (m, 2H), 3.99 (q, J = 9.9 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , , , , (q, J = 27.0 Hz), , , (q, J = 28.6 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 9.9 Hz). Q-TF (ESI) m/z [M-H] - calculated for C 15 H 8 F 3 S, ; found, (4-(Diphenylamino)phenyl)-3,3,3-trifluoropropan-1-one (2u) CF 3 N White solid (60%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 7.75 (d, J = 9.0 Hz, 2H), 7.35 (dd, J = 11.9, 4.0 Hz, 4H), (m, 6H), 6.97 (d, J = 9.0 Hz, 2H), 3.69 (q, J = 10.2 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , δ (q, J = Hz), δ (q, J = 27.8 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). HRMS (EI) m/z [M] + calculated for C 21 H 16 NF 3, ; found,
10 3,3,3-Trifluoro-1-(1-methyl-1H-indol-2-yl)propan-1-one (2v) N F 3 C White solid (66%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.24 (d, J = 1.2 Hz, 1H), 7.87 (dd, J = 8.7, 1.5 Hz, 1H), 7.37 (d, J = 8.8 Hz, 1H), 7.15 (d, J = 3.2 Hz, 1H), 6.63 (d, J = 3.2 Hz, 1H), 3.86 (q, J = 10.2 Hz, 2H), 3.84 (s, 3H), 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , δ (q, J = Hz), , , , , (q, J = 27.7 Hz), F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). Q-TF (ESI) m/z [M+H] + calculated for C 12 H 11 F 3 N, ; found, (Benzo[b]thiophen-3-yl)-3,3,3-trifluoropropan-1-one (2w) (Lit. 5 ) S F 3 C White solid (50%). M.P o C. 1 H NMR (300 MHz, CDCl 3 ) δ 8.77 (dd, J = 8.7, 0.7 Hz, 1H), 8.29 (s, 1H), (m, 1H), (m, 2H), 3.81 (q, J = 10.1 Hz, 2H). 13 C NMR (125 MHz, CDCl 3 ) δ , , , , , , , , (q, J = Hz), , (q, J = 28.2 Hz). 19 F NMR (471 MHz, CDCl 3 ) δ (t, J = 10.1 Hz). HRMS (EI) m/z [M] + calculated for C 11 H 7 F 3 S, ; found, References 1. N. Petr, L. Anton. Et al. J. Am. Chem. Soc., 2012, 134, Q.-Q. Lu, C. Liu. Et al. Chem. Commun., 2014, 50, K. R. Chung., C. Kun., Et al. Bioorganic & Medicinal Chemistry Letters. 1995, 5, A. Maji, A. Hazra, and D. Maiti. rg. Lett. 2014, 16, A. Deb, S. Manna., Angew. Chem. Int. Ed. 2013, 52, H NMR, 19 F NMR and 13 C NMR and spectra 1-(Biphenyl-4-yl)-3,3,3-trifluoropropan-1-one (2a) 10
11 11
12 1-(Biphenyl-3-yl)-3,3,3-trifluoropropan-1-one (2b) 12
13 13
14 3,3,3-Trifluoro-1-p-tolylpropan-1-one (2c) 14
15 1-(4-Tert-butylphenyl)-3,3,3-trifluoropropan-1-one (2d) 15
16 16
17 3,3,3-Trifluoro-1-(4-methoxyphenyl)propan-1-one (2e) 17
18 3,3,3-Trifluoro-1-(4-(methylthio)phenyl)propan-1-one (2f) 18
19 19
20 3,3,3-Trifluoro-1-(4-phenoxyphenyl)propan-1-one (2g) 20
21 1-(4-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2h) 21
22 22
23 1-(3-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2i) 23
24 1-(2-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2j) 24
25 25
26 1-(2-(Benzyloxy)phenyl)-3,3,3-trifluoropropan-1-one (2k) 26
27 3,3,3-Trifluoro-1-(4-(trifluoromethoxy)phenyl)propan-1-one (2l) 27
28 28
29 3,3,3-Trifluoro-1-(2-fluorobiphenyl-4-yl)propan-1-one (2m) 29
30 1-(3,5-Dichlorophenyl)-3,3,3-trifluoropropan-1-one (2n) 30
31 31
32 3,3,3-Tifluoro-1-(naphthalen-2-yl)propan-1-one (2o) 32
33 3,3,3-Trifluoro-1-(7-methoxynaphthalen-2-yl)propan-1-one (2p) 33
34 34
35 3,3,3-Trifluoro-1-(4'-fluorobiphenyl-4-yl)propan-1-one (2q) 35
36 3,3,3-Trifluoro-1-(9-phenyl-9H-carbazol-3-yl)propan-1-one (2r) 36
37 37
38 1-(Dibenzo[b,d]furan-4-yl)-3,3,3-trifluoropropan-1-one (2s) 38
39 1-(Dibenzo[b,d]thiophen-4-yl)-3,3,3-trifluoropropan-1-one (2t) 39
40 40
41 1-(4-(Diphenylamino)phenyl)-3,3,3-trifluoropropan-1-one (2u) 41
42 3,3,3-Trifluoro-1-(1-methyl-1H-indol-2-yl)propan-1-one (2v) 42
43 43
44 1-(Benzo[b]thiophen-3-yl)-3,3,3-trifluoropropan-1-one (2w) 44
45 45
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