Supplementary Material. An Efficient One-pot Synthesis of Symmetrical Diselenides or Ditellurides from Halides with CuO nanopowder/se 0 or Te 0 /Base
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1 Supplementary Material An Efficient One-pot Synthesis of Symmetrical Diselenides or Ditellurides from Halides with CuO nanopowder/se 0 or Te 0 /Base Devender Singh, Anna M. Deobald, Leandro R. S. Camargo, Greice Tabarelli, Oscar E. D. Rodrigues,,* and Antonio L. Braga,, * Departamento de Química, Universidade Federal de Santa Maria, , Santa Maria, RS, Brazil Departamento de Química, Universidade Federal de Santa Catarina, , Florianópolis, SC, Brazil albraga@qmc.ufsc.br, rodriguesoed@smail.ufsm.br S1
2 Contents General Information...S3 General procedure for the synthesis of Diselenides and ditellurides...s3 Spectroscopic Data....S4 Copies of 1 H NMR, 13 C NMR and mass spectrum of Compounds...S9 77 Se NMR spetra of diselenides.....s33 Mass spectra of selected dichalcogenides......s48 References....S51 S2
3 General Information: CuO nano particles (mean particle size, 33 nm, surface area, 29 m 2 /g and purity, 99.99%) were purchased from Sigma Aldrich. 1 H and 13 C NMR spectra were recorded at 400 and 100 MHz respectively with tetramethylsilane as internal standard. 77 Se NMR were recorded at MHZ respectively with diphenyl diselenide as a 77 Se external reference ( ppm). Column chromatography was performed using Merck Silica Gel ( mesh). Thin layer chromatography (TLC) was performed using Merck Silica Gel GF 254, 0.25 mm thickness. For visualization, TLC plates were either placed under ultraviolet light, or stained with iodine vapor, or acidic vanillin. All reagents used were purchased from Sigma Aldrich. 1 H and 13 C NMR spectral data of the compounds are identical to those reported. High resolution ESI mass spectra were obtained from a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer, an RF-only hexapole ion guide and an external electrospray ion source. General Procedure for the Synthesis of Diselenides: To a stirred solution of Se 0 metal (2.0 mmol) and halides (1.0 mmol) in dry DMSO (2.0 ml) was added CuO nanoparticles (10.0 mol %) followed by KOH (2.0 equiv) under nitrogen atmosphere at 90 0 C. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, which was subjected to column chromatographic separation to give pure Diselenides. The identity and purity of the product was confirmed by 1 H and 13 C NMR spectroscopic analysis. The same procedure was followed for the synthesis of Ditellurides. S3
4 Spectroscopic Data 1, 2-diphenyldiselenide (2a): 1, 7 Yield: 96%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 2H), (m, 3H); 13 C NMR (CDCl 3, 50 MHz); 77 Se NMR (CDCl 3, MHz) δ = 463.1; IR (KBr), ν (cm - 1): 3040, 1585, 1475, , 2-dip-tolyldiselenide (2b): 1,7 Yield: 96%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.47 (d, J= 8.4 Hz, 2H), 7.04 (d, J= 8.4 Hz, 2H), 2.30 (s, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , 22.80; 77 Se NMR (CDCl 3, MHz) δ = 409.6; IR (KBr), ν (cm - 1): 2916, 1627, 1396, , 2-dio-tolyldiselenide (2c): 5 Yield: 90%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.61 (d, J= 7.2 Hz, 1H), (m, 3H), 2.40 (s, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , , 22.17; 77 Se NMR (CDCl 3, MHz) δ = 405.2; IR (KBr), ν (cm - 1): 2908, 1581, 1288, , 2-bis (4-chlorophenyl)diselenide (2d): 1 Yield: 86%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.47 (d, J= 8.6 Hz, 2H), 7.20 (d, J= 8.6 Hz, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , ; 77 Se NMR (CDCl 3, MHz) δ = 449.3; IR (KBr), ν (cm - 1): 3070, 1465, 1002, 810. S4
5 1, 2-bis (2-chlorophenyl)diselenide (2e): 6 Yield: 90%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , ; 77 Se NMR (CDCl 3, MHz) δ = 476.9; IR (KBr), ν (cm - 1): 3070, 1465, 1080, ,2'-diselenidediyldiphenol (2f): 11 Yield: 72%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 1H), (m, 1H), 1.67 (br, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , ; 77 Se NMR (CDCl 3, MHz) δ = 329.1; IR (KBr), ν (cm - 1): 3425, 1411, 1041, ,2-bis(4-bromophenyl)diselenide (2g): 1,7 Yield: 89%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 4H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , ; 77 Se NMR (CDCl 3, MHz) δ = 457.6; IR (KBr), ν (cm - 1): 3040, 1465, 1010, ,2-bis(4-methoxyphenyl)diselenide (2h): 1, 7 Yield: 86%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.53 (d, J= 8.8 Hz, 2H), 6.83 (d, J= 8.8 Hz, 2H), 3.80 (s, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , 55.29; 77 Se NMR (CDCl 3, MHz) δ = 394.2; IR (KBr), ν (cm - 1): 2908, 1581, 1288, ,2-bis(3-methoxyphenyl)diselenide (2i): 7 Yield: 84%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 3H), (m, 1H), 3.74 (s,3h); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , , 55.19; 77 Se NMR (CDCl 3, MHz) δ = 333.2; IR (KBr), ν (cm - 1): 2939, 1573, 1284, 848. S5
6 1,2-bis(2-methoxyphenyl)diselenide (2j): 7 Yield: 84%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 2H), 3.88 (s, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , 97.48, 55.84; 77 Se NMR (CDCl 3, MHz) δ = 338.6; IR (KBr), ν (cm - 1): 2931, 1573, 1288, ,2-bis(2,4-dimethoxyphenyl)diselenide (2k): 12 Yield: 50%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 2H), 3.81 (s, 3H), 3.77 (s,3h); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , 98.50, 55.80, 55.41; 77 Se NMR (CDCl 3, MHz) δ = 413.3; IR (KBr), ν (cm - 1): 2931, 1589, 1211, ,2'-diselenidediyldianiline (2l): 8 Yield: 93%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.62 (dd, J 1 = 7.8 Hz, J 2 = 1.4 Hz, 1H), (m,1h), 6.72 (dd, J 1 = 7.8 Hz, J 2 = 1.4 Hz, 1H), (m, 1H), 4.05 (s, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , 84.11; 77 Se NMR (CDCl 3, MHz) δ = 405.3; IR (KBr), ν (cm - 1): 3441, 1612, 1311, ,2-di(pyridin-3-yl)diselenide (2m): 9 Yield: 82%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , ; 77 Se NMR (CDCl 3, MHz) δ = 473.9; IR (KBr), ν (cm - 1): 3441, 1558, 1002, 702. S6
7 4,4'-diselenidediyldibenzaldehyde (2n): yellow solid, melting point o C Yield: 72%; 1 H NMR (CDCl 3, 200 MHz): δ = 9.88 (s, 1H), 7.39 (d, J= 8.4 Hz, 2H), 7.14 (d, J= 8.4 Hz, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , ; 77 Se NMR (CDCl 3, MHz) δ = 481.3; IR (KBr), ν (cm - 1): 3422, 1635, 1157, 833. HRMS (ESI- FT-ICR) m/z: [M+] +; calcd. for C 7 H 6 OSe 2 fragment ,2-diheptyldiselenide (2o): 13 Yield: 96%; 1 H NMR (CDCl 3, 200 MHz): δ = 2.90 (t, J= 7.2 Hz, 2H), 1.72 (qui, J= 7.2 Hz, 2H), (m, 8H), (m, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = 31.68, 30.93, 30.16, 29.44, 28.76, 22.56, 14.02; 77 Se NMR (CDCl 3, MHz) δ = 509.6; IR (KBr), ν (cm - 1): 2924, 1705, 1111, ,2-diphenylditelluride (3a): 3 Yield: 86%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 2H), (m, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , ; IR (KBr), ν (cm - 1): 3016, 1566, 1465, ,2-dio-tolylditelluride (3b): 4 Yield: 88%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.46 (d, J= 7.6 Hz, 1H), (m, 2H), (m, 1H), 2.45 (s, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , , 26.85; IR (KBr), ν (cm - 1): 3040, 1897, 1442, ,2-di(pyridin-3-yl)ditelluride (3c): 10 Yield: 72%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 1H), (m, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , ; IR (KBr), ν (cm - 1): 3461, 1530, 1012, 702. S7
8 1,2-bis(4-chlorophenyl)ditelluride (3d): 4 Yield: 90%; 1 H NMR (CDCl 3, 200 MHz): δ = 7.66 (d, J= 8.4 Hz, 2H), 7.13 (d, J= 8.4 Hz, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , IR (KBr); ν (cm - 1): 3070, 1465, 1002, ,2'-ditelluridediyldiphenol (3e): 2 Yield: 86%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m, 1H), (m, 1H), (m, 1H), 1.68 (br, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , 83.44; IR (KBr), ν (cm - 1): 3430, 1460, 1000, ,2'- ditelluridediyldianiline (3f): 8 Yield: 90%; 1 H NMR (CDCl 3, 200 MHz): δ = (m, 1H), (m,1h), (m, 1H), (m, 1H), 4.16 (s, 2H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , , 94.69; IR (KBr), ν (cm - 1): 3440, 1632, 1372, ,2-bis(4-methoxyphenyl)ditelluride (3g): 2 Yield: 84%; 1 Hz NMR (CDCl 3, 200 MHz): δ = 7.66 (d, J= 8.8 Hz, 2H), 6.72 (d, J= 8.8 Hz, 2H), 3.76 (s, 1H); 13 C NMR (CDCl 3, 50 MHz) δ = , , , , 55.23; IR (KBr), ν (cm - 1): 3052, 1461, 1280, ,2-diheptylditelluride (3h): 14 Yield: 84%; 1 H NMR (CDCl 3, 200 MHz): δ = 2.62 (t, J= 7.4 Hz, 2H), (m, 2H), (m, 8H), (m, 3H); 13 C NMR (CDCl 3, 50 MHz) δ = 33.62, 32.00, 31.73, 28.64, 28.54, 22.61, 14.07; IR (KBr), ν (cm - 1): 2930, 1745, 1100, 810. S8
9 Copies of 1 H NMR and 13 C NMR 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1, 2-diphenyldiselenide (2a). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-diphenyldiselenide (2a). S9
10 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-dip-tolyldiselenide(2b). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-dip-tolyldiselenide(2b). S10
11 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-dio-tolyldiselenide(2c). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-dio-tolyldiselenide(2c). S11
12 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)diselenide(2d). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)diselenide(2d). S12
13 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(2-chlorophenyl)diselenide(2e). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(2-chlorophenyl)diselenide(2e). S13
14 1 H NMR (200 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldiphenol(2f). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldiphenol(2f). S14
15 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-bromophenyl)diselenide(2g). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-bromophenyl)diselenide(2g). S15
16 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-methoxyphenyl)diselenide(2h). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-methoxyphenyl)diselenide(2h). S16
17 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(3-methoxyphenyl)diselenide(2i). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(3-methoxyphenyl)diselenide(2i). S17
18 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(2-methoxyphenyl)diselenide(2j). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(2-methoxyphenyl)diselenide(2j). S18
19 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(2,4-dimethoxyphenyl)diselenide(2k). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(2,4-dimethoxyphenyl)diselenide(2k). S19
20 1 H NMR (200 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldianiline(2l). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldianiline(2l). S20
21 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-di(pyridin-3-yl)diselenide(2m). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-di(pyridin-3-yl)diselenide(2m). S21
22 1 H NMR (200 MHz, CDCl 3 ) spectrum of 4,4'-diselenidediyldibenzaldehyde(2n). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 4,4'-diselenidediyldibenzaldehyde(2n). S22
23 Mass spectrum of 4,4'-diselenidediyldibenzaldehyde(2n). S23
24 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-diheptyldiselenide(2o). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-diheptyldiselenide(2o). S24
25 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-diphenylditelluride (3a). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-diphenylditelluride (3a). S25
26 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-dio-tolylditelluride(3b). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-dio-tolylditelluride(3b). S26
27 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)ditelluride(3c). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)ditelluride(3c). S27
28 1 H NMR (200 MHz, CDCl 3 ) spectrum of 2,2'-ditelluridediyldiphenol(3d). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 2,2'-ditelluridediyldiphenol(3d). S28
29 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-methoxyphenyl)ditelluride(3e). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-methoxyphenyl)ditelluride(3e). S29
30 1 H NMR (200 MHz, CDCl 3 ) spectrum of 2,2'- ditelluridediyldianiline(3f). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 2,2'- ditelluridediyldianiline(3f). S30
31 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)ditelluride(3g). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)ditelluride(3g). S31
32 1 H NMR (200 MHz, CDCl 3 ) spectrum of 1,2-diheptylditelluride(3h). 13 C NMR (50 MHz, CDCl 3 ) spectrum of 1,2-diheptylditelluride(3h). S32
33 77 Se NMR spetra of diselenides Se Se 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1, 2-diphenyldiselenide (2a). S33
34 Se Se 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-di 4-tolyldiselenide(2b). S34
35 Se Se 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-di 2-tolyldiselenide(2c). S35
36 Cl Se Se Cl 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(4-chlorophenyl)diselenide(2d). S36
37 Cl Se Se Cl 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(2-chlorophenyl)diselenide(2e). S37
38 HO Se Se OH 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldiphenol(2f). S38
39 Br Se Se Br 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(4-bromophenyl)diselenide(2g). S39
40 O Se Se O 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(4-methoxyphenyl)diselenide(2h). S40
41 O Se Se O 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(3-methoxyphenyl)diselenide(2i). S41
42 O Se Se O 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(2-methoxyphenyl)diselenide (2j) S42
43 O O Se Se O O 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-bis(2,4-dimethoxyphenyl)diselenide(2k). S43
44 H 2 N Se Se NH 2 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 2,2'-diselenidediyldianiline(2l). S44
45 N Se Se N 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-di(pyridin-3-yl)diselenide(2m). S45
46 CHO Se Se OHC 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 4,4'-diselenidediyldibenzaldehyde(2n). S46
47 Se Se 77 Se NMR (76.28 MHz, CDCl 3 ) spectrum of 1,2-diheptyldiselenide(2o). S47
48 Mass spectra of selected dichalcogenides Se Se S48
49 Se) 2 N Se) 2 H 2 N Se Se NH 2 S49
50 O Se Se O Se Se O O Cl Se Se Cl S50
51 References. 1) Zhong, P.; Guo, M. P. synthetic commun. 2001, 31, ) Engman, L.;Persson, J. synthetic commun. 1993, 23, ) Chieffi, A.; Menezes, P. H.; Comasseto J. V. Organometallics, 1997, 16, ) Engman, L.;Persson, J. J. Organometallic Chemistry, 1990, 388, 71. 5) Kunio, H.; Shuko, S. Synthesis, 1985, 6-7, ) Kashurnikova, L. V.; Vinokurova, R. I. Zhurnal Organicheskoi Khimii, 1978, 14(12), ) Evers, M.; Christiaens, L. Tetrahedron Lett. 1983, 24, ) Wojtowicz, H.; Chojnacka, M.; Mlochowski, J.; Palus, J.; Syper, L.; Hudecova, D.; Uher, M.; Piasecki, E.; Rybka, M. Il Farmaco, 2003, 58, ) Dunne, S. J.; Summers, L. A.; Felsobuki, E. I. Journal of Heterocyclic Chemistry, 1992, 29, ) Bhasin, K. K.; Arora, V.; Klapötke, T. M.; Crawford, M. Eur. J. Inorg. Chem. 2004, 24, ) Ichikawa, H.; Usami, Y.; Arimoto M. Tetrahedron Lett. 2005, 46, ) Yvette, G. Chinese Journal of Chemistry, 1990, 3, ) Ming-De, R.; Hua-Rong, Z.; Wei-Qiang, F.; Xun-Jun, Z. Journal of Organometallic Chemistry, 1995, 485,19. 14) Merkel, G.; Berge, H.; Jeroschewski, P. Journal fuer Praktische Chemie, 1984, 326, 467. S51
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