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1 Supporting Information Visible Light Initiated Hantzsch Synthesis of 2,5-Diaryl Substituted Pyrroles at Ambient Conditions Tao Lei, Wen-Qiang Liu, Jian Li, Mao-Yong Huang, Bing Yang, Qing-Yuan Meng, Bin Chen, Chen-Ho Tung, and Li-Zhu Wu* Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, the Chinese Academy of Sciences, Beijing , P. R. China Table of Contents 1. Experimental details...s2 2. Characterization data for all compounds... S H and 13 C NMR...S10 1
2 1. Experimental details a) General Information 1 H NMR spectra were recorded using a Bruker Avance DPX 400 MHz instruent with tetramethylsilane (TMS) as an internal standard. 13 C NMR spectra were obtained at 100 MHz and referenced to the internal solvent signals. HRMS (ESI) spectra were recorded on Thermo Scientific Q Exactive Mass Spectrometer. ESR spectra were recorded at room temperature using a Bruker ESP-300E spectrometer at 9.8 GHz, X- band, with 100 Hz field modulation. Solvents were dried by the general methods before use. Photoirradiation was carried out with LEDs (blue light). Commercially available reagents were used without further purification. b) Preparation of the substrates. 1 Aniline (4 mmol), ethyl benzoylacetate (1 mmol) and AcOH (4 mmol) were stirred at 80 C for 5 h. The mixture is diluted with water (20 ml), extracted with EtOAC (50 ml), the combined organic phase was washed with brine, dried and concentrated. After flash column chromatography silica (petroleum / CH 2 Cl 2 gradient 2/1), the crude product was obtained. Further purification was carried out by recrystallization with n-hexane and ether. c) General procedure for construction of 2,5-Diaryl Substituted Pyrroles by visible light catalysis at Room Temperature A 10 ml Pyrex tube equipped with a magnetic stir bar was charged with enamine 1 (0.1 mmol), 2 (0.15 mmol), Ir(ppy) 3 (2 mol %), NEt 3 (35 mol %), DMSO (2 ml), in the Ar, under the irradiation of blue LED at room temperature for 2 hours. Then the mixture was evaporated under reduced pressure to remove the solvent and the residue was purified by flash chromatography on silica gel (petroleum ether/etoac) to afford the desired product. References: 2
3 [1]. S. Wurtz, S. Rakshit, J. J. Neumann, T. Droge, F. Glorius, Angew. Chem., Int. Ed. 2008, 47, Table S1. The optimization of conditions. a Entry Ir(ppy) 3 solvent TEA Yield (%) b 1 2 mol % DMSO mol % DMSO 35 mol % 99 3 c 2 mol % DMSO 35 mol % 0 4 d -- DMSO 35 mol % 0 a Reaction conditions: 1a (0.1 mmol), 2a (0.15 mmol), photocatalyst, additive, DMSO (2 ml), in the Ar, under the irradiation of blue LED at room temperature for 2 hours. b Isolated yield. c No light. d No photocatalyst. Figure 2. a) The absorption spectra of Ir(ppy) 3, 1a, 2a. in DMSO, [Ir(ppy) 3 ] = M, [1a]= M, [2a]= M. 3
4 b) Steady state luminescence quenching experiment in DMSO, [Ir(ppy) 3 ] = M, [1a]= M, [2a]= M. Excitation wavelength is 405 nm, emission wavelength is 530 nm. Figure S1. The absorption spectra of their mixture of Ir(ppy) 3 and 1a or 2a in DMSO, [Ir(ppy) 3 ] = M, [1a]= M, [2a]= M. 4
5 Figure S2. Luminescence quenching experiment in DMSO a) Steady state luminescence quenching experiment in DMSO. [Ir(ppy) 3 ] = M, [TEA]= M, [1a]= M, [2a]= M. Excitation wavelength is 405 nm, emission wavelength is 530 nm. b) Transient luminescence lifetime experiment in DMSO, [Ir(ppy) 3 ] = M, [TEA]= M, [1a]= M, [2a]= M. Excitation wavelength is 405 nm, emission wavelength is 530 nm. 5
6 c) Luminescence quenching spectra of Ir(ppy) 3 as a function of concentration of 1a. Inset is the Stern Volmer plot of Ir(ppy) 3 by 1a. The concentration of Ir(ppy) 3 is M. Excitation wavelength is 405 nm. d) Luminescence quenching phosphorescence spectra of Ir(ppy) 3 as a function of concentration of 2a. Inset is the Stern Volmer plot of Ir(ppy) 3 by 2a. The concentration of Ir(ppy) 3 is M. Excitation wavelength is 405 nm. 6
7 Figure S3. Cyclic Voltammetry (CV) Experiments: a) CV spectra of Ir(ppy) 3 and NBu 4 PF 6 in degassed DMSO, [Ir(ppy) 3 ]= M, [NBu 4 PF 6 ]= M. E ox =0.72 V vs SCE, E red = -2.3 V vs SCE. b) Normalization of UV-vis absorption(left) and luminescence (right) spectra of Ir(ppy) 3. 7
8 c) CV spectra of 1a and NBu 4 PF 6 in degassed DMSO, [1a]= M, [NBu 4 PF 6 ]= M. E ox = 0.90 V SCE, E red = -2.0 V SCE. d) CV spectra of 2a and NBu 4 PF 6 in degassed DMSO, [2a]= M, [NBu 4 PF 6 ]= M. E ox >1.6 V vs SCE, E red = -1.2 V vs SCE. 8
9 Figure S4. Photo-induced isomerization of 1a Figure S4. 1 H-NMR of system containing Ir(ppy) 3 and 1a in degassed DMSO-d 6, [Ir(ppy) 3 ]= M, [1a]= M. 1) before irradiation; 2) after irradiated by blue LEDs for 5 minute. HRMS (ESI) of radical intermediate captured by TEMPO. HRMS (ESI) Calcd. for C17H26NO2 [M+H ]: Found:
10 2. Characterization data for all compounds ethyl 1,2,5-triphenyl-1H-pyrrole-3-carboxylate(3a): solid, mp , yield: 36.5 mg, 99%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 11H), (m, 2H), 6.95 (s, 1H), (m, 2H), 4.17 (q, J = 7.1 Hz, 2H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.58, HRMS (ESI) Calcd. for C25H22NO2 [M+H ] + : Found: ethyl 2,5-diphenyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate(3b): solid, mp , yield: 34.4 mg, 90%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), (m, 3H), 6.79 (d, J = 8.1 Hz, 2H), 4.16 (q, J = 7.1 Hz, 2H), 2.24 (s, 3H), 1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.55, 21.07, HRMS (ESI) Calcd. for C26H24NO2 [M+H] + : Found: ethyl 2,5-diphenyl-1-(m-tolyl)-1H-pyrrole-3-carboxylate(3c): solid, mp , yield: 32.3 mg, 85%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), (m, 3H), 6.72 (s, 2H), 4.17 (q, J = 7.1 Hz, 2H), 2.13 (s, 3H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , 59.55, 21.08, HRMS (ESI) Calcd. for C26H24NO2 [M+H] + : Found: ethyl 2,5-diphenyl-1-(o-tolyl)-1H-pyrrole-3-carboxylate(3d): 10
11 solid, mp , yield: 38.1 mg, 91%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 15H), 4.18 (q, J = 6.9 Hz, 2H), 1.80 (s, 3H), 1.18 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , 59.60, 17.62, HRMS (ESI) Calcd. for C26H24NO2 [M+H] + : Found: ethyl 1-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3e): solid, mp , yield: 33.6 mg, 84%, petroleum ether/etoac = 60/1-40/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), 6.93 (s, 1H), 6.83 (d, J = 8.8 Hz, 2H), 6.65 (d, J = 8.8 Hz, 2H), 4.16 (q, J = 7.1 Hz, 2H), 3.71 (s, 3H), 1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.55, 55.28, HRMS (ESI) Calcd. for C26H24NO3 [M+H] + : Found: ethyl 1-(4-fluorophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3f): solid, mp , yield: 31.8 mg, 83%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), 6.94 (s, 1H), (m, 4H), 4.17 (q, J = 7.1 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , (d, J = 247 Hz), , , (d, J = 3.3 Hz), , , , (d, J = 8.6 Hz), , , , , , (d, J = 23 Hz), , , 59.65, F NMR (377 MHz, CDCl 3 ) δ HRMS (ESI) Calcd. for C25H21FNO2 [M+H] + : Found: ethyl 1-(4-chlorophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3g): 11
12 solid, mp , yield: 33.0 mg, 84%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 4H), 6.93 (s, 1H), 6.84 (d, J = 8.6 Hz, 2H), 4.17 (q, J = 7.1 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.67, HRMS (ESI) Calcd. for C25H21ClNO2 [M+H] + : Found: ethyl 1-(4-bromophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3h): solid, mp , yield: 29.7 mg, 67%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), (m, 2H), 6.93 (s, 1H), 6.77 (d, J = 8.6 Hz, 2H), 4.16 (q, J = 7.1 Hz, 2H), 1.16 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.67, HRMS (ESI) Calcd. for C25H21BrNO2 [M+H] + : Found: ethyl 1-(naphthalen-1-yl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3i): solid, mp , yield: 33.2 mg, 80%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 5H), (m, 11H), 4.19 (q, J = 7.1 Hz, 2H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , 59.68, HRMS (ESI) Calcd. for C29H24NO2 [M+H] + : Found: ethyl 1-benzyl-2,5-diphenyl-1H-pyrrole-3-carboxylate(3j): 12
13 liquid,, yield: 20.5 mg, 54%, petroleum ether/etoac = 60/1-40/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), (m, 3H), 6.73 (s, 1H), (m, 2H), 4.96 (s, 2H), 4.04 (q, J = 7.0 Hz, 2H), 1.03 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.43, 48.54, HRMS (ESI) Calcd. for C26H24NO2 [M+H] + : Found: ethyl 2-(4-methoxyphenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3k): solid, mp , yield: 34.8 mg, 88%, petroleum ether/etoac = 60/1-40/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), (m, 3H), 6.73 (d, J = 8.6 Hz, 2H), 4.19 (q, J = 7.1 Hz, 2H), 3.75 (s, 3H), 1.21 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.55, 55.10, HRMS (ESI) Calcd. for C26H24NO3 [M+H] + : Found: ethyl 2-(4-fluorophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3l): solid, mp , yield: 33.0 mg, 86%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), (m, 5H), 4.18 (q, J = 7.1 Hz, 2H), 1.20 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , (d, J = 246), , , , (d, J = 8.0 Hz), , , , , , , (d, J = 4.0 Hz), , , (d, J = 21 Hz), , 59.68, HRMS (ESI) Calcd. for C25H21FNO2 [M+H] + : Found: ethyl 2-(4-nitrophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3m): 13
14 solid, mp , yield: 23.6 mg, 57%,, petroleum ether/etoac = 60/1-40/1; 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 (d, J = 8.6 Hz, 2H), 7.36 (d, J = 8.6 Hz, 2H), (m, 6H), (m, 2H), 6.97 (s, 1H), 6.92 (d, J = 7.4 Hz, 2H), 4.21 (q, J = 7.1 Hz, 2H), 1.22 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.98, HRMS (ESI) Calcd. for C25H21N2O4 [M+H] + : Found: methyl 2-(4-fluorophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3n): solid, mp , yield: 29.6 mg, 80%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 2H), (m, 5H), 3.73 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , (d, J = 246 Hz), , , , (d, J = 8.0 Hz), , , , , , , (d, J = 4.0 Hz), , (d, J = 21.0 Hz), , , HRMS (ESI) Calcd. for C24H19FNO2 [M+H] + : Found: N,1,2,5-tetraphenyl-1H-pyrrole-3-carboxamide(3o): solid, mp , yield: 38.5 mg, 93%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), (m, 13H), 7.11 (s, 1H), (m, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , HRMS (ESI) Calcd. for C29H23N2O [M+H] + : Found: phenyl(1,2,5-triphenyl-1h-pyrrol-3-yl)methanone(3p): 14
15 solid, mp , yield: 17.9 mg, 45%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ 7.82 (d, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1H), 7.31 (t, J = 7.6 Hz, 2H), (m, 6H), (m, 7H), 6.98 (d, J = 6.4 Hz, 2H), 6.82 (s, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , HRMS (ESI) Calcd. for C29H22NO [M+H] + : Found: ethyl 1,2-diphenyl-5-(p-tolyl)-1H-pyrrole-3-carboxylate(3q): solid, mp , yield: 33.8 mg, 89%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 8H), (m, 7H), 4.17 (q, J = 7.1 Hz, 2H), 2.27 (s, 3H), 1.17 (t, J = 7.2 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , 59.56, 21.11, HRMS (ESI) Calcd. for C26H24NO2 [M+H] + : Found: ethyl 5-(4-nitrophenyl)-1,2-diphenyl-1H-pyrrole-3-carboxylate(3r): solid, mp , yield: 13.0 mg, 32%, petroleum ether/etoac = 60/1-40/1; 1 H NMR (400 MHz, CDCl 3 ) δ 8.03 (d, J = 8.7 Hz, 2H), (m, 12H), 6.94 (d, J = 7.3 Hz, 2H), 4.18 (q, J = 7.1 Hz, 2H), 1.17 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , 59.84, HRMS (ESI) Calcd. for C25H21N2O4 [M+H] + : Found: ethyl 5-(naphthalen-2-yl)-1,2-diphenyl-1H-pyrrole-3-carboxylate(3s): 15
16 solid, mp , yield: 30.6 mg, 73%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 3H), (m, 2H), (m, 9H), 7.07 (s, 1H), 6.96 (d, J = 6.8 Hz, 2H), 4.19 (q, J = 7.1 Hz, 2H), 1.19 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , , , , , 59.64, HRMS (ESI) Calcd. for C29H24NO2 [M+H] + : Found: ethyl 1,2-diphenyl-1,4-dihydroindeno[1,2-b]pyrrole-3-carboxylate(3t): solid, mp , yield: 11.7 mg, 31%, petroleum ether/etoac = 100/1-60/1; 1 H NMR (400 MHz, CDCl 3 ) δ 7.49 (d, J = 6.0 Hz, 1H), 7.34 (s, 3H), 7.23 (m, 7H), 7.08 (m, 2H), 6.74 (d, J = 6.3 Hz, 1H), 4.23 (q, J = 6.6 Hz, 2H), 3.81 (s, 2H), 1.26 (t, J = 6.7 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , , 59.60, 32.13, HRMS (ESI) Calcd. for C26H22NO2 [M+H] + : Found:
17 3. 1 H and 13 C NMR 1. ethyl 1,2,5-triphenyl-1H-pyrrole-3-carboxylate(3a): 17
18 2. ethyl 2,5-diphenyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate(3b): 18
19 3. ethyl 2,5-diphenyl-1-(m-tolyl)-1H-pyrrole-3-carboxylate(3c): 19
20 4. ethyl 2,5-diphenyl-1-(o-tolyl)-1H-pyrrole-3-carboxylate(3d): 20
21 5. ethyl 1-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3e): 21
22 6. ethyl 1-(4-fluorophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3f): 22
23 23
24 7. ethyl 1-(4-chlorophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3g): 24
25 8. ethyl 1-(4-bromophenyl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3h): 25
26 9. ethyl 1-(naphthalen-1-yl)-2,5-diphenyl-1H-pyrrole-3-carboxylate(3i): 26
27 10. ethyl 1-benzyl-2,5-diphenyl-1H-pyrrole-3-carboxylate(3j): 27
28 11. ethyl 2-(4-methoxyphenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3k): 28
29 12. ethyl 2-(4-fluorophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3l): 29
30 30
31 13. ethyl 2-(4-nitrophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3m): 31
32 14. methyl 2-(4-fluorophenyl)-1,5-diphenyl-1H-pyrrole-3-carboxylate(3n): 32
33 33
34 15. N,1,2,5-tetraphenyl-1H-pyrrole-3-carboxamide(3o): 34
35 16. phenyl(1,2,5-triphenyl-1h-pyrrol-3-yl)methanone(3p): 35
36 17. ethyl 1,2-diphenyl-5-(p-tolyl)-1H-pyrrole-3-carboxylate(3q): 36
37 18. ethyl 5-(4-nitrophenyl)-1,2-diphenyl-1H-pyrrole-3-carboxylate(3r): 37
38 19. ethyl 5-(naphthalen-2-yl)-1,2-diphenyl-1H-pyrrole-3-carboxylate(3s): 38
39 20. ethyl 1,2-diphenyl-1,4-dihydroindeno[1,2-b]pyrrole-3-carboxylate(3t): 39
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Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
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