Supporting Information
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- Παραμονος Κομνηνός
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Modular Synthesis of Propargylamine Modified Cyclodextrins by a Gold(III)-catalyzed Three Component Coupling Reaction Tsz-Wai Hui a,b, Jian-Fang Cui a,b and Man Kin Wong* a,b a. The Hong Kong Polytechnic University Shenzhen Research Institute, Shenzhen, PR China. b. State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, PR China. These authors contributed equally to this work mankin.wong@polyu.edu.hk Fax: Supporting Information S1
2 Literature references of modified β-cyclodextrins H.-S. Byun, N. Zhong, R. Bittman, rg. Synth. 2000, 77, Ts-β-CD C. Wang, F. Chen, X.-W. He, S.-Z. Kang, C.-C. You, Y. Liu. Analyst. 2001, 126, a S2
3 General Method: Chemicals were purchased from commercial sources and were used without further purification. 1-(p-Toluenesulfonyl)imidazole and 6--p-toluenesulfonyl-β-cyclodextrin (6-Ts-β-CD) were synthesized by following the literature procedure (rg. Synth. 2000, 77, ). 1 H, 13 C and 2D NMR spectra were performed at 600 MHz and 150 MHz on Bruker DPX-600 spectrometer. Chemical shifts (ppm) were referenced to residual solvent or TMS signals and coupling constants are given in Hz. Data for 1 H NMR were recorded as follows: chemical shift (δ, ppm), multiplicity (s, singlet; brs, broad singlet; d, doublet; dd, double doublet; t, triplet; td, triple doublet; tt, triple triplet; q, quartet; qd, quadruple doublet, m, multiplet), coupling constant (Hz), integration. Data for 13 C NMR are reported in terms of chemical shift (δ, ppm). Low resolution and high resolution mass spectra were measured on LCQ Advantage Mass, Waters 7890A and Waters Q-TF 2TM spectrometer. Infrared spectroscopy was conducted using Nicolet 380 FT- IR. General Procedure for Synthesis of Mono-(6-benzylamino-6-deoxy)-β-cyclodextrin 1 H H H H H Ts H 6-Ts- -CD R 1 70 o C, 16 h NH 2 R 1 NH H H H H 1a: (83%), R 1 =H 1b: (60%), R 1 =CH 3 H 1c: (50%), R 1 =CH 3 1d: (36%), R 1 =Cl H 1 Scheme S1. Synthesis of mono-(6-benzylamino-6-deoxy)-β-cyclodextrin 1 6--p-Toluenesulfonyl-β-cyclodextrin (3.0 g, 2.33 mmol) was heated in benzyl amine (20 ml) at 70 o C with stirring overnight. The resulting solution was added dropwise into excess acetone (150 ml). The resulting suspension was filtered to collect yellow solid. The yellow solid was then dissolved in water and heated up until all solid was dissolved. The solution was standed for overnight to allow precipitation of solid. The suspension was filtered to collect white solid. The S3
4 white solid was dried to constant weight under reduced pressure to give the corresponding mono- (6-benzylamino-6-deoxy)-β-cyclodextrins 1a-1d with moderate to good yield (36-83%). General Procedure for Synthesis of Mono-(6-(benzylpropargyl)amino-6-deoxy)-βcyclodextrin 2 Scheme S2. Synthesis of mono-(6-(benzylpropargyl)amino-6-deoxy)-β-cyclodextrin 2 Mono-(6-benzylamino-6-deoxy)-β-cyclodextrin 1 (1.0 equiv.), formaldehyde (10.0 equiv.), alkyne (10.0 equiv.) and potassium gold(iii) chloride KAuCl4 (2.5 mol%) were heated in water (10 ml) at 40 o C for 24 h. The resulting suspension was filtered to collect the solid. The solid was then dissolved in water and heated at 80 o C for 20 min. The insoluble solid was removed by filtration. The solution was allowed to stand in air and precipitate for few days. The suspension was filtered to collect the white solid. The white solid was dried to constant weight under reduced pressure to give the corresponding mono-(6-benzylpropargylamino-6-deoxy)-βcyclodextrin 2a-2h with moderate to good yield (26-67%). S4
5 Table S1 Attempt of gold(iii) catalyzed three component coupling reaction of primary amine modified β-cyclodextrin, phenylacetylene and various aldehydes. [a] Entry R Catalyst Solvent Yield of 2aa (%) [b] 1 H KAuCl4 H2 0 2 Ph KAuCl4 H MeC6H4 KAuCl4 H N2C6H4 KAuCl4 H2 0 5 PhCH2CH2 KAuCl4 H2 0 6 CH3 KAuCl4 H2 0 7 n-c3h7 KAuCl4 H2 0 8 n-c6h13 KAuCl4 H2 0 [a] Reaction conditions: 1aa (0.1 mmol), aldehyde (1.0 mmol), phenylacetylene (1.0 mmol), 40 o C, 24 h. [b] Detected by ESI-MS and TLC analysis. Scheme S3. Proposed reaction mechanism S5
6 Characterization Data of Mono-(6-benzylamino-6-deoxy)-β-cyclodextrin 1 and Mono-(6- benzylpropargylamino-6-deoxy)-β-cyclodextrin 2 White solid; 60% yield; 1 H NMR (600 MHz, d 6 -DMS): δ 7.19 (d, J = 7.8 Hz, 2H, Ar-H), 7.10 (d, J = 7.9 Hz, 2H, Ar- H), (m, 15H, -2, -3, NH), (m, 7H, H-1), (m, 6H, -6), (m, 42H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1 ), 2.90 (d, J = 11.7 Hz, 1H, H-6a ), 2.72 (dd, J = 12.2, 6.8 Hz, 1H, H-6b ), 2.28 (s, 3H, CH3); 13 C NMR (150 MHz, d 6 -DMS): δ 138.4, 135.8, 129.1, 128.2, 102.8, 102.4, 102.3, 102.2, 84.2, 82.00, 81.96, 81.93, 81.8, , 71.0, , 53.3, 49.5, 21.2; IR (cm -1, KBr): 3414, 2927, 1653, 1636, 1560, 1541, 1502, 1458, 1419, 1374, 1157, 1079, 1031, 948, 756, 706, 582; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C50H80N , found White solid; 50% yield; S6
7 1 H NMR (600 MHz, d 6 -DMS): δ 7.22 (d, J = 8.1 Hz, 2H, Ar-H), 6.86 (d, J = 8.2 Hz, 2H, Ar- H), (m, 15H, -2, -3, NH), 4.84 (s, 7H, H-1), 4.54 (m, 6H, -6), 3.73 (s, 3H, Me), (m, 42H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1 ), 2.90 (d, J = 11.4 Hz, 1H, H- 6a ), 2.72 (s, 1H, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 158.4, 133.4, 129.4, 113.9, 102.8, 102.4, , , 84.2, 82.0, 81.9, 81.83, 81.82, , 71.0, , 55.5, 52.9, 49.3; IR (cm -1, KBr): 3366, 2929, 1637, 1514, 1420, 1368, 1302, 1247, 1156, 1079, 1031, 947, 757, 707, 582; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C50H80N , found White solid; 36% yield; 1 H NMR (600 MHz, d 6 -DMS): δ 7.35 (s, 4H, Ar-H), (5.85 (d, J = 6.5 Hz, 1H), (m, 13H), -2, -3), (m, 7H, H-1), (m, 6H, -6), (m, 42H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1 ), 2.90 (d, J = 11.4 Hz, 1H, H-6a ), 2.73 (dd, J = 11.8, 6.7 Hz, 1H, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 140.6, 131.4, 130.0, 128.4, 102.8, , , , 102.3, 84.2, 82.02, 81.97, 81.93, 81.85, , 71.0, , 52.6, 49.3; IR (cm -1, KBr): 3373, 2928, 1637, 1492, 1410, 1368, 1300, 1244, 1205, 1156, 1079, 1031, 947, 858, 757, 706, 581, 531; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C49H77ClN , found S7
8 White solid; 50% yield; 1 H NMR (600 MHz, d 6 -DMS): δ 7.47 (dd, J = 6.5, 2.8 Hz, 2H, Ar-H), (m, 3H, Ar- H), 7.34 (dt, J = 15.1, 7.4 Hz, 4H, Ar-H), 7.24 (t, J = 7.0 Hz, 1H, Ar-H), 5.98 (d, J = 6.4 Hz, 1H, -2 or -3), (m, 13H, -2, -3), 4.96 (d, J = 3.1 Hz, 1H, H-1), (m, 6H, H-1), (m, 6H, -6), (m, 44H, H-2, H-3, H-4, H-5, H-6a, H-6b, H- 1, H-2 ), (m, 2H, H-6a, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 139.5, 131.9, 129.1, , , 127.4, 123.2, 102.8, 102.6, 102.5, 102.4, 102.1, 86.1, 85.4, 84.2, 82.1, 81.94, 81.88, 81.8, 81.6, , , 58.6, 54.3, 43.5; IR (cm -1, KBr): 3384, 2927, 1637, 1491, 1419, 1369, 1156, 1079, 1029, 947, 862, 757, 701, 581, 528; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C58H84N , found White solid; 51% yield; S8
9 1 H NMR (600 MHz, d 6 -DMS): δ (m, 2H, Ar-H), 7.39 (d, J = 3.8 Hz, 3H, Ar-H), 7.23 (d, J = 7.5 Hz, 2H, Ar-H), 7.13 (d, J = 7.5 Hz, 2H, Ar-H), (m, 14H, -2, - 3), (m, 7H, H-1), 4.52 (s, 6H, -6), 3.87 (s, 44H, H-2, H-3, H-4, H-5, H-6a, H-6b, H- 1, H-2 ), 2.91 (dd, J = 39.3, 10.7 Hz, 2H, H-6a, H-6b ), 2.30 (s, 3H, CH 3 ); 13 C NMR (150 MHz, d 6 -DMS): δ 136.4, 131.9, 129.2, 128.7, 128.5, 126.0, 123.2, 102.7, 102.6, , , , 102.0, 86.2, 85.3, 84.1, 82.1, 81.94, 81.85, 81.8, 81.5, , , 58.6, 54.3, 43.7, 21.3; IR (cm -1, KBr): 3374, 2927, 1637, 1514, 1491, 1414, 1368, 1244, 1156, 1079, 1030, 946, 860, 758, 693, 581, 527; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C59H86N , found White solid; 42% yield; 1 H NMR (600 MHz, d 6 -DMS): δ (m, 5H, Ar-H), 7.25 (d, J = 8.1 Hz, 2H, Ar-H), 6.89 (d, J = 8.2 Hz, 2H, Ar-H), 5.97 (d, J = 5.7 Hz, 1H, -2 or -3), (m, 13H, -2, -3), (m, 7H, H-1), 4.58 (m, 6H, -6), 3.74 (s, 3H, Me), (m, 44H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1, H-2 ), (m, 2H, H-6a, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 158.8, 131.9, 131.1, 130.5, 129.1, 128.7, 123.2, 114.0, 102.7, 102.5, , , 102.1, 86.2, 85.4, 84.0, 82.3, 82.0, 81.9, 81.8, 81.6, , , 58.0, 55.5, 55.3, 54.2, 43.1; IR (cm -1, KBr): 3393, 2928, 1636, 1513, 1491, 1419, 1369, 1302, 1248, 1156, 1079, 1029, 946, 758, 693, 581, 528; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C59H86N , found S9
10 White solid; 49% yield; 1 H NMR (600 MHz, d 6 -DMS): δ (m, 2H, Ar-H), (m, 7H, Ar-H), 5.97 (d, J = 6.4 Hz, 1H, -2 or -3), (m, 13H, -2, -3), 4.93 (d, J = 3.1 Hz, 1H, H-1), (m, 6H, H-1), (m, 6H, -6), (m, 44H, H-2, H-3, H-4, H- 5, H-6a, H-6b, H-1, H-2 ), (m, 2H, H-6a, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 138.5, 131.9, 131.1, 129.1, 128.8, 128.6, 126.0, 123.1, 102.8, , , , , 102.1, 86.0, 85.4, 84.2, 82.1, 82.0, 81.84, 81.80, 81.7, , , 58.1, 54.2, 43.7; IR (cm -1, KBr): 3373, 2928, 1637, 1491, 1410, 1368, 1336, 1245, 1156, 1079, 1029, 946, 860, 758, 694, 582, 528; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C58H82ClN , found White solid; 50% yield; 1 H NMR (600 MHz, d 6 -DMS): δ 7.41 (d, J = 8.7 Hz, 2H, Ar-H), (m, 4H, Ar-H), 7.23 (t, J = 6.7 Hz, 1H, Ar-H), 6.94 (d, J = 8.8 Hz, 2H, Ar-H), 5.98 (d, J = 6.5 Hz, 1H, -2 or -3), (m, 13H, -2, -3), 4.96 (d, J = 3.1 Hz, 1H, H-1), 4.85 (dd, J = 7.8, 3.4 S10
11 Hz, 6H, H-1), (m, 6H, -6,), (m, 47H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1, H-2, Me), 2.91 (dt, J = 14.4, 9.6 Hz, 2H, H-6a, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 159.8, 139.8, 133.6, 129.3, 128.9, 127.5, 115.4, 114.9, 103.0, 102.8, 102.7, 102.6, 102.3, 85.6, 84.4, 84.3, 82.3, 82.2, 82.14, 82.07, 82.0, 81.8, , , 58.6, 55.9, 54.3, 43.6; IR (cm -1, KBr): 3373, 2928, 1637, 1607, 1510, 1413, 1368, 1338, 1293, 1249, 1156, 1079, 1029, 946, 834, 755, 704, 580, 533; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C59H86N , found White solid; 67% yield; 1 H NMR (600 MHz, d 6 -DMS): δ 7.43 (d, J = 8.1 Hz, 2H, Ar-H), (m, 6H, Ar-H), 7.24 (t, J = 6.7 Hz, 1H, Ar-H), 5.98 (d, J = 6.4 Hz, 1H, -2 or -3), (m, 13H, -2, -3), 5.29 (t, J = 5.8 Hz, 1H, PhCH2), 4.96 (d, J = 3.0 Hz, 1H, H-1), (m, 6H, H-1), (m, 8H, -6, PhCH 2 ), (m, 44H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1, H-2 ), 2.93 (dt, J = 14.5, 9.5 Hz, 2H, H-6a, H-6b ); 13 C NMR (150 MHz, d 6 -DMS): δ 143.5, 139.8, 132.0, 129.3, 128.9, 127.6, 127.2, 121.6, 103.0, 102.8, 102.7, 102.6, 102.3, 85.8, 85.6, 84.3, 82.3, 82.2, 82.1, 82.0, 81.8, , 63.2, , 58.6, 54.2, 43.6; IR (cm -1, KBr): 3373, 2927, 1636, 1508, 1413, 1368, 1246, 1205, 1156, 1079, 1029, 946, 848, 754,703, 581, 530; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C59H86N , found S11
12 White solid; 52% yield; 1 H NMR (600 MHz, d 6 -DMS): δ (m, 4H, Ar-H), 7.21 (t, J = 7.0 Hz, 1H, Ar-H), 5.99 (t, J = 5.8 Hz, 1H, -2 or -3), (m, 13H, -2, -3), 4.93 (d, J = 3.3 Hz, 1H, H-1), 4.84 (dd, J = 13.8, 3.6 Hz, 6H, H-1), (m, 6H, -6), (m, 43H, H-2, H-3, H-4, H-5, H-6a, H-6b, H-1, H-2 ), 3.15 (d, J = 17.0 Hz, 1H, H-2 ), 2.83 (d, J = 13.2 Hz, 1H, H-6a ), 2.76 (dd, J = 13.9, 5.9 Hz, 1H, H-6b ), (m, 1H), (m, 2H), (m, 2H); 13 C NMR (150 MHz, d 6 -DMS): δ 139.6, 129.0, 128.6, 127.2, 102.8, 102.6, 102.5, , , 102.0, 88.9, 84.2, 82.1, 82.0, 81.9, 81.6, 81.5, , 70.8, , 57.9, 55.4, 42.9, 31.2, 8.64, 8.61; IR (cm -1, KBr): 3374, 2929, 1636, 1409, 1369, 1331, 1250, 1203, 1156, 1032, 947, 863, 754, 701, 581, 531; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C55H83N , found White solid; 26% yield; S12
13 1 H NMR (600 MHz, d 6 -DMS): δ 7.31 (d, J = 4.3 Hz, 4H, Ar-H), (m, 1H, Ar-H), 6.04 (s, 1H, vinyl CH), 6.00 (d, J = 6.3 Hz, 1H, -2 or -3), (m, 13H, -2, - 3), (m, 7H, H-1), (m, 6H, -6), (m, 44H, H-2, H-3, H-4, H- 5, H-6a, H-6b, H-1, H-2 ), 2.92 (d, J = 13.4 Hz, 1H, H-6a ), 2.78 (dd, J = 13.6, 6.3 Hz, 1H, H- 6b ), 2.09 (d, J = 10.9 Hz, 4H, allyl CH 2 ), 1.58 (ddd, J = 10.9, 9.0, 5.4 Hz, 4H, -CH 2 CH 2 -); 13 C NMR (150 MHz, d 6 -DMS): δ 139.7, 134.3, 129.3, 128.8, 127.5, 120.8, 103.0, 102.8, 102,7, 102.6, 102.3, 87.3, 84.7, 83.4, 82.3, 82.1, 81.9, 81.7, , , 59.1, 55.6, 55.3, 43.9, 29.8, 25.7, 22.6, 21.8; IR (cm -1, KBr): 3382, 2927, 1637, 1419, 1369, 1243, 1156, 1079, 1029, 946, 847, 755, 704, 581, 531; MS (ESI): m/z ([M+H] + ); HRMS (ESI): Calcd. For C58H88N , found S13
14 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 1b S14
15 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 1c S15
16 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) of 1d S16
17 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2a S17
18 CSY (600 MHz, d 6 -DMS) spectrum of 2a S18
19 RESY (600 MHz, d 6 -DMS) spectrum (300ms) of 2a S19
20 RESY (600 MHz, d 6 -DMS) spectrum (600ms) of 2a S20
21 HSQC (600 MHz, d 6 -DMS) spectrum of 2a S21
22 HMBC (600 MHz, d 6 -DMS) spectrum of 2a S22
23 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2b S23
24 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2c S24
25 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2d S25
26 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2e f1 (ppm) S26
27 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2f S27
28 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2g S28
29 1 H NMR (600 MHz, d 6 -DMS) and 13 C NMR (150 MHz, d 6 -DMS) spectra of 2h f1 (ppm) S29
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