Electronic Supplementary Information (ESI)
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- λατίνος Βέργας
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea Porcheddu a and Lidia De Luca* a Dipartimento di Chimica e Farmacia, Università degli Studi di Sassari, Sassari, Italy ldeluca@uniss.it S1
2 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry 1. Experimental Procedures for Amides 4a-q and Product Characterization S References S8 3. MR Spectra of Compounds 4a-q S9-42 S2
3 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Experimental Procedures General Information. All reagents and solvents were as obtained by commercial source. All the reactions were carried out under 2 atmosphere using standard techniques. Column chromatography was generally performed on silica gel (pore size 60 A, mm particle size) and reactions were monitored by thin-layer chromatography (TLC) analysis was performed with Merck Kieselgel 60 F254 plates and visualized using UV light at 254 nm and KMn4 staining. 1H MR and 13C MR spectra were measured on a Bruker Avance III 400 spectrometer (400 MHz or 100 MHz, respectively) with CDCl3 as solvent and recordered in ppm relative to internal tetramethylsilane standard. The peak patterns are indicated as follows: s, singlet; d, doublet; t, triplet; m, multiplet; q, quartet; br, broad. The coupling constants, J, are reported in Hertz (Hz). The IR spectra were recorded on a Jasco FTIR-480 Plus Fourier Transform spectrometer. Melting points were determined in open capillary tubes and are uncorrected. High resolution mass spectroscopy data of the product were collected on a Waters Micromass GCT instrument. General procedures for amides 4a-q: An amine (0.32 mmol) was added to a solution of -chlorosuccinimide (0.352 mmol) in 10 ml of acetonitrile under 2 atmosphere and at room temperature. The reaction was monitored by TLC until disappearance of the amine (1-2 hours), then were added an alcohol (1.6 mmol), TBHP (1.6 mmol, 0.22 ml of a 70 wt% in water) and FeCl 3. 6H 2 (0.045 mmol) under 2 atmosphere. The resulting reaction mixture was heated in an oil bath at 85 C (the reaction was monitored by TLC until disappearance of - chloroamine). Then the reaction mixture was quenched with 20 ml of a saturated solution of a 2 S 3 (for removal of excess TBHP) and extracted three times with 40 ml of diethyl ether. The combined organic phases were dried over anhydrous a 2 S 4 and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to provide the desired amides 4a-q. S3
4 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Compound characterizations,-dibenzylbenzamide (4a). 1 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 4.2/0.8), R f = 0.44, to afford a white solid in 96% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 4.39 (s, 2H), 4.70 (s, 2H), (m, 2H), (m, 11H), (m, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 46.8, 51.4, 126.7, 127.0, 127.5, 128.4, 128.5, 128.7, 129.6, 136.2, 172.2; IR (neat) ν = 3058, 3028, 2924, 1633, 1494, 1452, 1423, 1362, 1265, 1143, 1076, 1027, 991, 736, 700. Me,-dibenzyl-4-methoxybenzamide (4b). 12 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 3.8/1.2), R f = 0.38, to afford a white solid in 74% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 3.80 (s, 3H), 4.48 (br s, 2H), 4.67 br (s, 2H), 6.88 (d, J = 8.8 Hz, 2H), (m, 10H), 7.48 (d, J = 8.5 Hz, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 44.1, 55.2, 60.3, 113.8, 126.9, 127.5, 128.2, 128.5, 128.7, 136.9, 160.2, 172.2; IR (neat) ν = 3062, 2924, 2853, 1629, 1513, 1494, 1421, 1363, 1265, 1176, 1030, 993, 738, 701.,-dibutyl-2-methylbenzamide (4c). Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 4/1), R f = 0.51, to afford a pale yellow oil in 76% yield; 1 H MR (400 MHz, CDCl 3 ) δ 0.74 (t, J = 7.2 Hz, 2H), 0.98 (t, J = 7.4 Hz, 2H), 1.1 (q, J = 7.4 Hz, 2H), (m, 4H), (m, 2H), 2.28 (s, 3H), 3.04 (t, J = 7.4 Hz, 2H), 3.3 (br s, 2H), 3.65 ( br s, 2H), (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 13.7, 14.1, 19.1, 19.9, 20.6, 29.8, 30.8, 44.2, 48.2, 125.8, 125.9, 128.6, 130.4, 134.1, 137.4, 171.4; IR (neat) ν = 2958, 2931, 2869, 1633, 1463, 1423, 1376, 1301, 1261, 746. HRMS (EI) ([M + ]) Calcd. For C 16 H 25 : , Found: morpholino(o-tolyl)methanone (4d). 2 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 2.5/2.5), R f = 0.31, to afford a yellow oil in 86% yield; 1 H MR (400 MHz, CDCl 3 ) δ 2.32 (s, 3H), 3,24 (br d, J = 4,5 Hz, 2H), 3.57 (br t, J = 4.5 Hz, 2H), (br m, 4H), (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 19.1, 41.9, 47.3, 66.9, 67.0, 125.8, 126.0, 129.1, 130.5, 134.2, 135.6, 170.1; IR (neat) ν = 3054, 2983, 2923, 2859, 1633, 1431, 1265, 1157, morpholino(4-nitrophenyl)methanone (4e). 2 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 2.5/2.5), R f = 0.23, to afford a white solid in 77% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ (br m, 8H), 7.61 (d, J = 8.8 Hz, 2H), 8.31 (d, J = 8.8 Hz, 2H); 13 C MR (100 MHz, S4
5 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry CDCl 3 ) δ 42.6, 48.0, 66.8, 124.0, 128.2, 141.4, 148.5, 168.1; IR (neat) ν = 2922, 2856, 1637, 1523, 1435, 1352, 1279, 1113, 1012, 895, 839, 735. F (4-fluorophenyl)(piperidin-1-yl)methanone (4f). 3 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 3/2), R f = 0.2, to afford a pale yellow oil in 70% yield; 1 H MR (400 MHz, CDCl 3 ) δ 1.57 (br s, 2H), 1.71 (br s,4h), 3.37 (br s, 2H), 3.71 (br s, 2H), (m, 2H), (m, 2H), 13 C MR (100 MHz, CDCl 3 ) δ 24.6, 25.7, 26.6, 43.2, 48.9, 115.3, 115.6, 129.0, 129.1, 132.4, 132.5, 161.9, 164.4, 169.4; IR (neat) ν = 2942, 1628, 1442, 1265, 1157, 1004, 847, 739. Cl (4-chlorophenyl)(piperidin-1-yl)methanone (4g). 3 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 3/2), R f = 0.2, to afford a white solid in 69% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 1.54 (br, s, 2H), 1.70 (br s, 4H), 3.35 (br s, 2H), 3.71 (br s, 2H), (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 24.5, 25.6, 26.6, 43.2, 48.9, 128.4, 128.7, 134.8, 135.4, 169.2; IR (neat) ν = 2937, 1629, 1440, 1277, 1090, 1003, 737. Br (4-bromophenyl)(piperidin-1-yl)methanone (4h). 4 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 3/2), R f = 0.23, to afford a white solid in 80% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 1.54 (br s, 2H), 1.70 (br s, 4H), 3.26 (br s, 2H), 3.71 (br s, 2H), 7.29 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 24.5, 25.6, 26.5, 43.3, 48.8, 123.6, 128.6, 131.6, 135.3, 169.3; IR (neat) ν = 2933, 2854, 1631,1441, 1277, 1111, 1068, 1001, 833, 733. Cl (3-chlorophenyl)(piperidin-1-yl)methanone (4i). 5 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 3.8/1.2), R f = 0.45, to afford a yellow oil in 58% yield; 1 H MR (400 MHz, CDCl 3 ) δ 1.55 (br s, 4H),1.71 (br s, 4H), 3.35 (br s, 2H), 3.72 (br s, 2H), (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 24.5, 25.6, 26.6, 43.2, 48.8, 124.9, 127.0, 129.5, 129.8, 134.5, 138.2, 168.7; IR (neat) n = 2931, 2856, 1631, 1566, 1439, 1280, 800, benzyl--methylbenzamide (4j). 4 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 3.5/1.5), R f =0.26,to afford a pale yellow oil in 79% yield; 1 H MR (400 MHz, CDCl 3 ) δ 2.89 (br s, 1.5H), 3.06 (br s, 1.5H), 4.54 (br s, 1H), 4.79 (br s, 1H), (m, 10H); 13 C MR (100 MHz, CDCl 3 ) δ 33.2, 37.1, 50.8, 55.2, 126.8, 127.0, 127.6, 127.9, 128.2, 128.4, 128.8, 129.6, 136.3, 136.6, 137.1, 170.8, 171.6; IR (neat) ν = 2921, 1631, 1450, 1400, 1265, 1070, 1026, 698. S5
6 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S,-dibenzylthiophene-2-carboxamide (4k). 1 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 3/2), R f = 0.58, to afford a white solid in 98% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 4.75 (s, 4H), 6.98 (dd, J = 3.7 Hz, J = 5.1Hz, 1H), (m, 11H), 7.47 (dd, J = 1.2 Hz, J = 5.1Hz, 1H); 13 C MR (100 MHz, CDCl 3 ) δ 50.1, 126.9, 127.6, 128.6, 128.8, 129.3, 136.6, 137.7, IR (neat) ν = 3062, 3004, 2978, 2954, 2914, 1611, 1583, 1519, 1494, 1453, 1422, 1364, 1347, 1306, 1250, 1078, 889. piperidin-1-yl(o-tolyl)methanone (4l). 6 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 3.5/1.5), R f = 0.38, to afford a pale yellow oil in 85% yield; 1 H MR (400 MHz, CDCl 3 ) δ 1.46 (s, 2H), 1.66 (s, 4H), 2.31 (s, 3H), 3.17 (d, J = 4.1 Hz, 2H), 3.71 (br s, 1H), 3.79 (br s, 1H), 7.21 (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 18.9, 24.5, 25.7, 26.5, 42.3, 47.8, 125.6, 125.8, 128.5, 130.2, 134.0, 136.7, 169.8; IR (neat) ν = 3049, 2938, 2857, 1627, 1444, 1350, 1288, 1271, 1240, 1129, 1097, 1027, 1000, 733, 700, 665. S H -benzylthiophene-2-carboxamide (4m). 7 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 2.5/2.5), R f =0.35, to afford a pale yellow oil in 63% yield; 1 H MR (400 MHz, CDCl 3 ) δ 4.64 (d, J = 5.7Hz, 2H), 6.35 (br s, 1H), 7.09 (dd,, J = 3.7 Hz, J = 5.1Hz, 1H), (m, 1H), (m, 4H), 7.50 (dd,, J = 1.2 Hz, J = 5.1Hz, 1H), 7.53 (dd,, J = 1.1 Hz, J = 2.5Hz, 1H); 13 C MR (100 MHz, CDCl 3 ) δ 44.0, 127.6, 127.7, 127.9, 128.1, 128.8, 130.0, 138.0, 138.7, 161.8; IR (neat) ν = 2922, 1629, 1545, 1421, 1265, 737. H -pentylbenzamide (4n). 8 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 2.5/2.5), R f =0.51,to afford a pale yellow oil in 92% yield; 1 H MR (400 MHz, CDCl 3 ) δ 0.94 (t, J = 7.1Hz, 3H), 1.38 (m, 4H), 1.64 (t, J = 7.3Hz, 2H), 3.47 (q, J = 7.2 Hz, 2H), 6.19 (br s, 1H), (m, 3H), 7.78 (m, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 14.0, 22.4, 29.1, 29.4, 40.1, 126.8, 128.5, 131.3, 134.9, 167.5; IR (neat) ν = 3064, 2956, 2929, 2860, 1639, 1576, 1545, 1491, 1464, 1375, 1309, 1209, 1153, 1074, 1028, 928, 877, 804, 698. H -heptylbiphenyl-4-carboxamide (4o). Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-acet = 4/1), R f =0.39,to afford a pale yellow oil in 72% yield; 1 H MR (400 MHz, CDCl 3 ) δ 0.91 (t, J = 6.9 Hz, 3H), (m, 8H), (m, 2H), 3.50 (q, J = 6.9 Hz, 2H), 6.18 (br s, 1H), 7.41 (t, J = 7.3 Hz, 1H), 7.49 (t, J = 7.7Hz, 2H), (m, 4H), 7.85 (d, J = 8.5Hz, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 14.1, 22.6, 27.0, 29.0, 29.7, 31.8, 40.1, 127.1, 127.2, 127.3, 127.9, 128.9, 133.5, 140.1, 144.1, 167.2; ; IR (neat) ν = 3041, 2922, 2852, 1630, 1537, 1469, 1265, 850, 740; HRMS (EI) ([M + ]) Calcd. For C 20 H 25 : , Found: H -butylnaphthalene-2-carboxamide (4p). 9 Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 3/2), R f = 0.25, to afford a white solid in 81% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 1.01 (t, J = 7.3 Hz, 3H), (m, 2H), (m, 2H), 3.57 (q, J =8.4 Hz, 2H), 6.00 (br s, 1H), S6
7 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry (m, 1H), (m, 3H), (m, 2H), 8.31 (d, J = 8.3 Hz, 1H); 13 C MR (100 MHz, CDCl 3 ) δ 13.8, 20.2, 31.8, 39.8, 124.7, 125.4, 126.4, 127.1, 128.3, 130.1, 133.7, 134.9, IR (neat) ν = 3051, 2927, 1637, 1539, 1460, 1304, 1257, 1151, 1020, 779, 734. H methyl 4-(phenethylcarbamoyl)benzoate (4q). Prepared according to the general procedure. The product was purified by flash chromatography on silica gel (v/v petroleum ether-et 2 = 2/3), R f =0.34, to afford a white solid in 98% yield (m.p C); 1 H MR (400 MHz, CDCl 3 ) δ 2.97 (t,, J = 6.8 Hz, 2H), 3.76 (q,, J = 6.2 Hz, 2H), 3.95 (s, 3H), 6.23 (br s, 1H), (m, 5H), 7.76 (d, J = 8.3 Hz, 2H), 8.09 (d, J = 8.3 Hz, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 35.6, 41.2, 52.4, 126.7, 126.9, 128.7, 128.8, 129.8, 132.7, 138.5, 138.7, 166.3, IR (neat) ν = 3327, 2923, 1720, 1635, 1543, 1439, 1280, 1196, 1157, 1113, 870, 821, 739, 698; HRMS (EI) ([M + ]) Calcd. For C 17 H 17 3 : , Found: S7
8 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry References R. Cadoni, A. Porcheddu, G. Giacomelli and L. De Luca, rg. Lett., 2012, 14, T. T. Dang, Z. Yinghuai, S. C. Ghosh, C. Anqi, C. L. L. Chai and A. M. Seayad, Chem. Commun., 2012, 48, J. Li, F. Xu, Y. Zhang and Q. Shen, J. rg. Chem., 2009, 74, G.-L. Li, K. K.-Y. Kung and M.-K. Wong, Chem. Commun., 2012, 48, I. E. Pop, B. P. Déprez and A. L. Tartar, J. rg. Chem., 1997, 62, A. Porcheddu and L. De Luca, Adv. Synth. Cat. 2012, 354, Gernigon, R. M. Al-Zoubi and D. G. Hall, J. rg. Chem., 2012, 77, M. Mori and Y. Ban, Chem. arm. Bull., 1976, 24, K. R. Reddy, C. U. Maheswari, M. Venkateshwar and M. L. Kantam, Eur. J. rg. Chem., 2008, 21, S8
9 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry a S9 ppm ppm
10 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry a S ppm
11 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Me 4b S11 10ppm
12 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Me 4b S ppm
13 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry c S13 ppm ppm
14 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry c S ppm
15 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S15 ppm ppm
16 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry d S16 0 ppm ppm
17 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry e S17 ppm ppm
18 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry e S18 0 ppm ppm
19 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry F 4f S19 ppm ppm
20 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry F 4f S20 0 ppm ppm
21 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Cl 4g S21 ppm ppm
22 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Cl 4g S22 0 ppm ppm
23 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Br 4h S23 ppm ppm
24 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Br 4h S24 0 ppm ppm
25 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Cl 4i S25 ppm ppm
26 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Cl 4i S26 0 ppm ppm
27 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry j S27 ppm ppm
28 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry j S28 0 ppm ppm
29 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S 4k S29 ppm ppm
30 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S 4k S ppm
31 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry l S31 ppm ppm
32 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry l S ppm
33 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S 4m H S33 ppm 10ppm
34 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry S 4m H S34 0 ppm ppm
35 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4n S35 ppm ppm
36 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4n S36 0 ppm ppm
37 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4o S37 ppm ppm
38 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4o S38 0 ppm ppm
39 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4p S39 ppm ppm
40 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4p S40 0 ppm ppm
41 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4q S41 ppm ppm
42 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry H 4q 1 1 S42 ppm ppm
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