N-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of -methylanilines with isocyanides Arvind K. Yadav and Lal Dhar S. Yadav* Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad , India ldsyadav@hotmail.com Contents: Page o. I. General Information 2 II. General procedure for the synthesis of compound 3 2 III. General procedure for the synthesis of compounds 4a and 5a 3-4 IV. Reduction and hydrolysis of compound 3a 3 V. n/off visible light irradiation experiment 4 VI. The quantum yield determination of 3a 4 VII. Spectral data of synthesized compounds 3, 4a and 5a 5-9 VIII. 1 H and 13 C MR Copies of synthesised compounds IX. Reference 45 Figure. 1 Experimental setup. 1
2 I. General Information: All commercially available reagents were used without further purification unless otherwise specified by a reference. Solvents were purified by the usual methods and stored over molecular sieves. All reactions were performed using oven-dried glassware. rganic solutions were concentrated using a Buchi rotary evaporator. Column chromatography was carried out over silica gel (Merck mesh) and TLC was performed using silica gel GF254 (Merck) plates. Melting points (mps) were determined by open glass tube and are uncorrected. The absorbance values of the samples were measured using potassium Reineckate as an actinometer. IR spectra in KBr were recorded on a Perkin-Elmer 993 IR spectrophotometer and 1 H (400 MHz), 13 C (100 MHz) MR spectra were recorded on a Bruker AVII spectrometer in CDCl 3 using TMS as internal reference. All chemical shifts are reported in δ/ppm and coupling constants (J) in Hertz (Hz). MS (EI) spectra were recorded on double focusing mass spectrometer. White light LEDs (7 W) was purchased from commercial supplier Luxeon Star LEDs Quadica Developments Inc. 47 6th Concession Rd. Brantford, ntario 32 5L7 Canada. II. General procedure for the synthesis of compound 3: A round bottom flask was charged with -methylaniline 1 (1.0 mmol), isocyanide 2 (1.0 mmol) and HPI (10 mol%) in CH 3 C (3 ml). The contents were irradiated from upper side of the flask using Luxeon Rebel high power white LEDs (7 W) with stirring under nitrogen atmosphere at room temperature for h. After the completion of reaction (as indicated by TLC), it was quenched with water (5 ml) and extracted with ethyl acetate (3 5 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the crude product, which was purified by silica gel column chromatography using a mixture of EtAc-hexane to give the pure product 3. Scheme 1 Gram scale synthesis of 3-iminoindole. 2
3 S abh 4 + H 3 B 3 (1:1) rt, 1 h, no solvent 3a Scheme 2 Reduction of product 3a into 4a. 4a H S III. General procedure for the reduction of compound 3a into 4a: A mixture of imine 3a (1.0 mmol), sodium borohydride (1.0 mmol) and boric acid (1.0 mmol) was ground with an agate mortar and pestle at room temperature for 1.0 h until TLC showed complete disappearance of the starting material. The reaction mixture was quenched with water (5 ml) and extracted with ethyl acetate (3 5 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the crude product, which was purified by silica gel column chromatography using a mixture of EtAc-hexane to give the pure product 4a. 3a S PTSA /H 2 50 o C, 2 h 5a Scheme 3 Hydrolysis of product 3a into 5a. IV. General procedure for the hydrolysis of compound 3a into 5a: A mixture of imine 3a (1.0 mmol) was stirred with PTSA/H 2 (1.0 equiv., 1:1) in DCE (3 ml) for 2.0 h at 50 o C until TLC showed complete disappearance of the starting material. It was extracted with ethyl acetate (3 5 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the crude product, which was purified by silica gel column chromatography using a mixture of EtAchexane to give the pure product 5a. 3
4 C S 2a CH 3 C, 2, 12 h, rt S 1a (2 equiv.) 3a traces Scheme 4 TEMP mediated intermolecular cyclization of,-dimethylaniline with TosMIC. V. n/off visible light irradiation experiment: Figure 2. n/off visible light irradiation experiment. VI. Determination of quantum yield (ф): The reaction mixture was irradiated with high-power LED (7 W) for 12 h (Figure 2). The photon flux was estimated to be E s-1 by using potassium Reineckate as an actinometer. 1 The rate of formation of 3a was obtained by 1 H MR spectrum of the crude product using acetonitrile as internal standard. It was found to be mol s -1, which was converted into quantum yield ф =
5 VII. Spectral data of synthesised compounds 3, 4a and 5a. Compound 3a: White solid, mp: o C; IR (KBr): 3394, 3360, 3140, 2942, 2821, 2258, 1657, 1596, 1499, 1322, 1139, 735, 681, 672 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.73 (d, J = 8.1 Hz, 2H), (m, 3H), 6.90 (t, J = 7.2 Hz, 1H), 6.68 (d, J = 8.1 Hz, 2H), 4.69 (s, 2H), 3.75 (s, 2H), 2.99 (s, 3H), 2.45 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.1, 154.7, 135.2, 131.4, 128.7, 128.3, 127.2, 121.4, 118.6, 117.1, 115.0, 71.1, 47.4, 37.3, HRMS (EI) calcd. for C 17 H S + : , found Compound 3b: White solid, mp: o C; IR (KBr): 3524, 3403, 3339, 3141, 2922, 2813, 1643, 1340, 1123, 857, 672 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.74 (d, J = 8.1 Hz, 1H), (m, 6H), (m, 2H), 4.68 (s, 2H), 3.70 (s, 2H), 3.01 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.3, 154.9, 133.5, 131.3, 130.2, 128.5, 125.9, 121.6, 118.3, 117.2, 114.8, 70.4, 47.2, HRMS (EI): calcd. for C 16 H S , found Compound 3c: White solid, mp: o C; IR (KBr): 3541, 3421, 3317, 3134, 3073, 2936, 2841, 1637, 1539, 1327, 1142, 1039, 721, 675 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.58 (s, 1H), 7.29 (d, J = 7.1 Hz, 4H), 7.04 (d, J = 7.2 Hz, 1H), 6.78 (d, J = 7.2 Hz, 1H), 4.67 (s, 2H), 3.61 (s, 2H), 3.01 (s, 3H), 2.34 (s, 3H), 2.32 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 152.0, 135.5, 130.1, 129.7, 128.7, 128.4, 128.1, 125.3, 115.6, 115.2, 71.0, 46.9, 37.4, 21.2, HRMS (EI) calcd. for C 18 H S + : , found Compound 3d: White solid, mp: o C; IR (KBr): 3473, 3342, 3152, 3042, 2978, 2831, 1634, 1547, 1321, 1137, 1119, 781 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.69 (s, 1H), 7.30 (d, J = 7.2 Hz, 4H), 6.79 (d, J = 8.2 Hz, 1H), 6.58 (d, J = 8.1 Hz, 1H), 4.69 (s, 2H), 3.79 (s, 3H), 3.62 (s, 2H), 3.02 (s, 3H), 2.32 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.9, 149.7, 146.2, 134.4, 129.6, 128.5, 128.1, 119.9, 117.5, 116.3, 114.7, 70.3, 54.8, 46.7, 37.3, HRMS (EI) calcd. for C 18 H S + : , found
6 Compound 3e: White solid: mp: o C; IR (KBr): 3427, 3334, 2924, 2826, 1649, 1332, 1263, 817, 642, cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.68 (s, 1H), 7.37 (d, J = 8.2 Hz, 1H), (m, 4H), 6.68 (d, J = 8.2 Hz, 1H), 4.65 (s, 2H), 3.65 (s, 2H), 3.07 (s, 3H), 2.34 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 154.8, 135.3, 134.6, 133.2, 130.8, 128.9, 128.1, 118.5, 116.4, 112.3, 70.6, 47.3, 37.4, HRMS (EI) calcd. for C 17 H 17 Br 2 2 S + : , found Compound 3f: Yellow solid: mp: o C; IR (KBr): 3327, 3134, 2927, 2824, 1648, 1567, 1481, 1357, 1242, 1263, 819, 643, cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 8.32 (s, 1H), 7.91 (d, J = 8.7 Hz, 1H), 7.73 (m, 4H), 7.08 (d, J = 8.2 Hz, 1H), 4.67 (s, 2H), 3.45 (s, 2H), 3.07 (s, 3H), 2.33 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 160.8, 139.3, 137.4, 135.8, C, C, 127.2, 123.8, 122.9, 113.6, 71.5, 47.4, 37.3, HRMS (EI) calcd. for C 17 H S + : , found Compound 3g: Yellow oily liquid; IR (KBr): 2942, 2834, 1664, 1595, 1337, 1247, 1134, 781 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.72 (d, J = 8.2 Hz, 1H), 7.27 (t, J = 8.2 Hz, 1H), (m, 5H), 6.89 (t, J = 8.2 Hz, 2H), 3.95 (s, 2H), 3.07 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.4, 154.6, 151.0, 131.3, 130.0, 128.5, 121.7, 119.8, 118.1, 117.3, 115.6, 48.1, HRMS (EI): calcd. for C 15 H : , found Compound 3h: Yellow viscous solid; IR (KBr): 3147, 2963, 2842, 1633, 1526, 1307, 1253, 1141, 784 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 8.31 (d, J = 8.9 Hz, 1H), (m, 2H), (m, 2H), 7.14 (d, J = 8.9 Hz, 1H), (m, 2H), 3.98 (s, 2H), 3.78 (s, 3H), 3.07 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.1, 158.9, 155.2, 143.5, 131.7, 122.6, 121.3, 118.5, 117.4, 115.9, 114.7, 55.6, 47.7, HRMS (EI): calcd. for C 16 H : , found Compound 3i: White solid, mp: o C; IR (KBr): 2943, 2836, 1664, 1449, 1257, 831, 671 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.57 (d, J = 7.3 Hz, 1H), 7.50 (d, J = 8.1 Hz, 2H), 7.32 (t, J = 7.2 Hz, 2H), 6.98 (d, J = 8.2 Hz, 1H), (m, 2H), 3.69 (s, 2H), 3.01 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.8, 155.6, 149.4, 6
7 132.2, 131.3, 130.0, 122.7, 121.1, 118.9, 117.3, 115.6, 48.7, HRMS (EI): calcd. for C 15 H 13 Cl 2+ : , found Compound 3j: Yellow solid, mp: o C; IR (KBr): 3203, 2946, 2837, 1672, 1567, 1481, 1357, 1242, 725, 580, cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 8.19 (d, J = 9.2 Hz, 2H), 7.59 (d, J = 8.2 Hz, 1H), 7.34 (t, J = 7.6 Hz, 1H), 6.92 (d, J = 9.2 Hz, 2H), (m, 2H), 3.67 (s, 2H), 3.03 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 165.3, 157.2, 155.4, 146.3, 131.8, 125.7, 123.6, 121.1, 118.9, 117.5, 115.0, 48.7, HRMS (EI) calcd. for C 15 H : , found Compound 3k: Yellow oily liquid; IR (KBr): 3221, 3141, 2952, 2834, 1669, 1254, 853, 776 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.67 (d, J = 8.2 Hz, 1H), 7.35 (t, J = 8.2 Hz, 1H), (m, 2H), 3.56 (s, 2H), 3.01 (s, 3H), 1.26 (s, 9H); 13 C MR (CDCl 3, 100 MHz): δ = 164.1, 155.3, 130.9, 121.7, 120.4, 118.8, 117.1, 51.3, 48.5, 37.2, HRMS (EI) calcd. for C 13 H : , found Compound 3l: Yellow oily liquid; IR (KBr): 3146, 2933, 2844, 1673, 1256, 910, 874, 776, 574 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = (m, 2H), 7.13 (t, J = 7.2 Hz, 1H), 7.05 (t, J = 7.2 Hz, 1H), 3.58 (s, 2H), 3.02 (s, 3H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 3H), (m, 1H) 2.95 (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 1H), (m, 3H), (m, 1H); 13 C MR (CDCl 3, 100 MHz): δ = 164.3, 155.1, 130.7, 121.4, 121.0, 118.9, 117.2, 56.7, 47.3, 36.8, 32.3, 24.7, HRMS (EI) calcd. for C 15 H : , found Compound 3m: Yellow oily liquid; IR (KBr): 3140, 2947, 2861, 1682, 1253, 828, 728, 700 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.59 (d, J = 8.1 Hz, 1H), 6.96 (t, J = 7.2 Hz, 1H), (m, 2H), 3.85 (t, J = 6.2 Hz, 2H), 3.65 (s, 2H), 3.02 (s, 3H), (m, 2H), (m, 6H), 0.83 (t, J = 6.9 Hz, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 155.3, 131.4, 121.3, 121.1, 118.5, 117.2, 54.7, 47.6, 36.9, 31.6, 31.4, 25.6, 22.3, HRMS (EI) calcd. for C 15 H : , found
8 Compound 3n: Yellow oily liquid; IR (KBr): 3114, 2937, 2845, 1662, 1243, 820, 721, 707 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.56 (d, J = 8.2 Hz, 1H), 7.40 (t, J = 8.2 Hz, 2H), (m, 3H), 6.90 (t, J = 8.2 Hz, 1H), 6.86 (d, J = 7.3 Hz, 2H), 3.61 (s, 2H), 1.39 (s, 9H); 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 154.3, 151.2, 131.0, 129.4, 127.2, 121.6, 119.4, 118.0, 117.2, 115.7, 54.1, 39.8, HRMS (EI) calcd. for C 18 H : , found Compound 3o: Yellow oily liquid; IR (KBr): 3213, 3140, 2936, 2844, 1678, 1251, 823, 710 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.56 (d, J = 8.2 Hz, 1H), (m, 2H), (m, 3H), 6.88 (t, J = 8.2 Hz, 1H), 6.86 (d, J = 7.3 Hz, 2H), 3.64 (s, 2H), 3.28 (q, J = 6.3 Hz, 2H), 1.14 (t, J = 6.4 Hz, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 168.4, 154.7, 151.3, 131.1, 130.3, 127.0, 121.4, 119.7, 118.5, 117.3, 115.2, 45.5, 44.3, HRMS (EI) calcd. for C 16 H : , found Compound 3p: White solid: mp o C; IR (KBr): 3183, 3047, 2850, 1656, 1248, 723, cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.56 (d, J = 8.2 Hz, 1H), (m, 7H), (m, 3H), (m, 2H), 6.72 (d, J = 8.1 Hz, 1H), 3.46 (s, 2H), 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 151.3, 148.9, 143.2, 131.3, 130.1, 129.4, 127.2, 121.8, 121.3, 120.6, 119.7, 119.1, 118.0, 116.5, HRMS (EI) calcd. for C 20 H : , found Compound 3q: Yellow oily liquid; IR (KBr): 3227, 3140, 2957, 2834, 1667, 1250, 851, 778, cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = (m, 3H), (m, 4H), 6.72 (t, J = 8.1 Hz, 1H), 3.41 (s, 2H), 3.04 (s, 3H), 2.21 (s, 3H), 13 C MR (CDCl 3, 100 MHz): δ = 164.5, 151.0, 145.6, 133.2, 130.1, 128.5, 127.4, 119.3, 118.8, 118.1, 115.6, 48.2, 38.5, HRMS (EI) calcd. for C 16 H : , found Compound 3r: Yellow oily liquid; IR (KBr): 3173, 3053, 2856, 1650, 1241, 720, cm - 1 ; 1 H MR (CDCl 3, 400 MHz): δ = (m, 3H), (m, 3H), 6.64 (d, J = 8.1 Hz, 1H), 6.21 (s, 1H), 3.43 (s, 2H), 3.01 (s, 3H), 2.32 (s, 3H), 13 C MR (CDCl 3, 100 MHz): δ = 164.7, 154.6, 151.1, 141.2, 131.0, 129.2, 127.4, 119.1, 117.6, 8
9 114.3, 112.5, 48.1, 37.0, HRMS (EI) calcd. for C 16 H : , found Compound 4a: White solid, mp: o C; IR (KBr): 3464, 3367, 3143, 2945, 2826, 2251, 1590, 1493, 1325, 1141, 737, 687, 670 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.68 (d, J = 8.1 Hz, 2H), (m, 3H), 6.92 (t, J = 7.2 Hz, 1H), 6.65 (d, J = 8.1 Hz, 2H), 5.04 (brs, 1H), 4.13 (t, J = 7.4 Hz, 1H), 3.93 (dd, J = 7.2 Hz, 1H), 3.79 (dd, J = 7.2 Hz, 1H), 3.75 (s, 2H), 2.49 (s, 3H), 2.34 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 151.9, 138.6, 135.4, 129.7, 128.1, 127.2, 126.4, 121.6, 118.1, 108.9, 70.8, 63.0, 57.3, 40.4, HRMS (EI) calcd. for C 17 H S + : , found Compound 5a: Yellow oily liquid; IR (KBr): 3360, 3367, 3143, 2940, 2823, 2257, 1723, 1589, 1490, 1321, 1148, 691, 667 cm -1 ; 1 H MR (CDCl 3, 400 MHz): δ = 7.63 (d, J = 8.3 Hz, 1H), (m, 1H), (m, 2H), 4.57 (s, 2H), 3.04 (s, 3H); 13 C MR (CDCl 3, 100 MHz): δ = 183.9, 154.1, 134.2, 129.4, 121.3, 118.5, 117.1, 66.9, HRMS (EI) calcd. for C 9 H 9 + : , found
10 VIII. 1 H and 13 C MR Copies of synthesised compounds. Compound 3a. 1 H MR Spectrum (CDCl 3 ). S 3a 10
11 Compound 3a. 13 C MR Spectrum (CDCl 3 ). S 3a 11
12 Compound 3b. 1 H MR Spectrum (CDCl 3 ). S 3b 12
13 Compound 3b. 13 C MR Spectrum (CDCl 3 ). S 3b 13
14 Compound 3c. 1 H MR Spectrum (CDCl 3 ). S 3c 14
15 Compound 3c. 13 C MR Spectrum (CDCl 3 ). S 3c 15
16 Compound 3d. 1 H MR Spectrum (CDCl 3 ). S 3d 16
17 Compound 3d. 13 C MR Spectrum (CDCl 3 ). S 3d 17
18 Compound 3e. 1 H MR Spectrum (CDCl 3 ). Br S 3e 18
19 Compound 3e. 13 C MR Spectrum (CDCl 3 ). Br S 3e 19
20 Compound 3f. 1 H MR Spectrum (CDCl 3 ). 2 S 3f 20
21 Compound 3f. 13 C MR Spectrum (CDCl 3 ). 2 S 3f 21
22 Compound 3g. 1 H MR Spectrum (CDCl 3 ). 3g 22
23 Compound 3g. 13 C MR Spectrum (CDCl 3 ). 3g 23
24 Compound 3h. 1 H MR Spectrum (CDCl 3 ). 3h 24
25 Compound 3h. 13 C MR Spectrum (CDCl 3 ). 3h 25
26 Compound 3i. 1 H MR Spectrum (CDCl 3 ). 3i Cl 26
27 Compound 3i. 13 C MR Spectrum (CDCl 3 ). 3i Cl 27
28 Compound 3j. 1 H MR Spectrum (CDCl 3 ). 3j 2 28
29 Compound 3j. 13 C MR Spectrum (CDCl 3 ). 3j 2 29
30 Compound 3k. 1 H MR Spectrum (CDCl 3 ). 3k 30
31 Compound 3k. 13 C MR Spectrum (CDCl 3 ). 3k 31
32 Compound 3l. 1 H MR Spectrum (CDCl 3 ). 3l 32
33 Compound 3l. 13 C MR Spectrum (CDCl 3 ). 3l 33
34 Compound 3m. 1 H MR Spectrum (CDCl 3 ). 3m 34
35 Compound 3m. 13 C MR Spectrum (CDCl 3 ). 3m 35
36 Compound 3n. 1 H MR Spectrum (CDCl 3 ). 3n 36
37 Compound 3n. 13 C MR Spectrum (CDCl 3 ). 3n 37
38 Compound 3o. 1 H MR Spectrum (CDCl 3 ). 3o 38
39 Compound 3o. 13 C MR Spectrum (CDCl 3 ). 3o 39
40 Compound 3p. 1 H MR Spectrum (CDCl 3 ). Ph 3p 40
41 Compound 3p. 13 C MR Spectrum (CDCl 3 ). Ph 3p 41
42 Compound 3q. 1 H MR Spectrum (CDCl 3 ). 3q 42
43 Compound 3q. 13 C MR Spectrum (CDCl 3 ). 3q 43
44 Compound 3r. 1 H MR Spectrum (CDCl 3 ). 3r 44
45 Compound 3r. 13 C MR Spectrum (CDCl 3 ). 3r IX. Reference: 1 M. Majek, F. Filace and A. J. Wangelin, Beilstein J. rg. Chem., 2014, 10,
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