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1 Supporting Information Catalytic chalcogenylation under greener conditions: A solvent-free sulfur- and seleno-functionalyzation of olefins via I 2 /DMSO oxidant system André A. Vieira, b Juliano B. Azeredo, a Marcelo Godoi, c Claudio Santi, d Eufrânio N. da Silva Júnior e and Antonio L. Braga *a a Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil. Fax: ; Tel: ; braga.antonio@ufsc.br b Instituto de Química, Departamento de Química Orgânica, Universidade Federal da Bahia, Campus de Ondina, Salvador, , Brazil. c Escola de Química e Alimentos, Universidade Federal do Rio Grande Campus Santo Antônio da Patrulha, RS, Brazil. d Dipartimento di Scienze Farmaceutiche, Univesità di Perugia, Via del Liceo 1, 06134, Perugia, Italy. e Universidade Federal de Minas Gerais, Instituto de Ciências Exatas, Departamento de Química. Av. Antônio Carlos, Belo Horizonte, MG Brazil. 1
2 Table of Contents 1.1. NMR Spectra Mass Spectra IR Spectra
3 1.1. NMR spectra S1. 1 H NMR spectrum of compound 3a in CDCl 3 (200 MHz). S2. 13 C NMR spectrum of compound 3a in CDCl 3 (50 MHz). 3
4 S3. 1 H NMR spectrum of compound 3b in CDCl 3 (200 MHz). S4. 13 C NMR spectrum of compound 3b in CDCl 3 (50 MHz). 4
5 S5. 1 H NMR spectrum of compound 3d in CDCl 3 (200 MHz). S6. 13 C NMR spectrum of compound 3d in CDCl 3 (50 MHz). 5
6 S7. 1 H NMR spectrum of compound 3e in CDCl 3 (200 MHz). S8. 13 C NMR spectrum of compound 3e in CDCl 3 (50 MHz). 6
7 S9. 1 H NMR spectrum of compound 3f in CDCl 3 (200 MHz). S C NMR spectrum of compound 3f in CDCl 3 (50 MHz). 7
8 Normalized Intensity 1.0 Entry AV-32s.001.esp Chemical Shift (ppm) S11. 1 H NMR spectrum of compound 3g in CDCl 3 (200 MHz). S C NMR spectrum of compound 3g in CDCl 3 (50 MHz). 8
9 S13. 1 H NMR spectrum of compound 3h in CDCl 3 (200 MHz). S C NMR spectrum of compound 3h in CDCl 3 (50 MHz). 9
10 S15. 1 H NMR spectrum of compound 3i in CDCl 3 (200 MHz). S C NMR spectrum of compound 3i in CDCl 3 (50 MHz). 10
11 Normalized Intensity 1.0 B esp Chemical Shift (ppm) S17. 1 H NMR spectrum of compound 3j in CDCl 3 (200 MHz). S C NMR spectrum of compound 3j in CDCl 3 (50 MHz). 11
12 S19. 1 H NMR spectrum of compound 3k in CDCl 3 (200 MHz). S C NMR spectrum of compound 3k in CDCl 3 (50 MHz). 12
13 S21. 1 H NMR spectrum of compound 3m in CDCl 3 (200 MHz). S C NMR spectrum of compound 3m in CDCl 3 (50 MHz). 13
14 S23. 1 H NMR spectrum of compound 3n in CDCl 3 (200 MHz). S C NMR spectrum of compound 3n in CDCl 3 (50 MHz). 14
15 S25. 1 H NMR spectrum of compound 3o in CDCl 3 (200 MHz). S C NMR spectrum of compound 3o in CDCl 3 (50 MHz). 15
16 S27. 1 H NMR spectrum of compound 3r in CDCl 3 (200 MHz) S C NMR spectrum of compound 3r in CDCl 3 (50 MHz). 16
17 S29. 1 H NMR spectrum of compound 3s in CDCl 3 (200 MHz). S C NMR spectrum of compound 3s in CDCl 3 (50 MHz). 17
18 S31. 1 H NMR spectrum of compound 3t in CDCl 3 (200 MHz). S C NMR spectrum of compound 3t in CDCl 3 (50 MHz). 18
19 S33. 1 H NMR spectrum of compound 5a in CDCl 3 (200 MHz). S C NMR spectrum of compound 5a in CDCl 3 (50 MHz). 19
20 S35. 1 H NMR spectrum of compound 5b in CDCl 3 (200 MHz). S C NMR spectrum of compound 5b in CDCl 3 (50 MHz). 20
21 Normalized Intensity Normalized Intensity 1.0 fid.txt Chemical Shift (ppm) S37. 1 H NMR spectrum of compound 5c in CDCl 3 (400 MHz). 1.0 fid.txt Chemical Shift (ppm) S C NMR spectrum of compound 5c in CDCl 3 (100 MHz). 21
22 Normalized Intensity Normalized Intensity 1.0 fid.txt Chemical Shift (ppm) S39. 1 H NMR spectrum of compound 5d in CDCl 3 (400 MHz). 1.0 fid.txt Chemical Shift (ppm) S C NMR spectrum of compound 5d in CDCl 3 (100 MHz). 22
23 S41. 1 H NMR spectrum of compound 5e in CDCl 3 (200 MHz). S C NMR spectrum of compound 5e in CDCl 3 (50 MHz). 23
24 S43. 1 H NMR spectrum of compound 5f in CDCl 3 (200 MHz). S C NMR spectrum of compound 5f in CDCl 3 (50 MHz). 24
25 Normalized Intensity Normalized Intensity 1.0 fid.txt Chemical Shift (ppm) S45. 1 H NMR spectrum of compound 6a in CDCl 3 (400 MHz). 1.0 fid.txt Chemical Shift (ppm) S C NMR spectrum of compound 6a in CDCl 3 (100 MHz). 25
26 Normalized Intensity Normalized Intensity 1.0 B esp Chemical Shift (ppm) S47. 1 H NMR spectrum of compound 7a in CDCl 3 (400 MHz) 1.0 fid.txt Chemical Shift (ppm) S C NMR spectrum of compound 7a in CDCl 3 (100 MHz). 26
27 S49. 1 H NMR spectrum of compound 8a in CDCl 3 (200 MHz). S C NMR spectrum of compound 8a in CDCl 3 (100 MHz). 27
28 S51. 1 H NMR spectrum of compound 9a in CDCl 3 (200 MHz). S C NMR spectrum of compound 9a in CDCl 3 (50 MHz). 28
29 1.2. Mass Spectra S53. High Resolution Chemical Ionization Mass Spectra for Compound 3b. S54. High Resolution Chemical Ionization Mass Spectra for traces of Compound 3c. 29
30 S55. High Resolution Chemical Ionization Mass Spectra for Compound 3d. S56. High Resolution Chemical Ionization Mass Spectra for Compound 3e. S57. High Resolution Chemical Ionization Mass Spectra for Compound 3f. 30
31 S58. High Resolution Chemical Ionization Mass Spectra for Compound 3g. S59. High Resolution Chemical Ionization Mass Spectra for Compound 3i. S60. High Resolution Chemical Ionization Mass Spectra for Compound 3j. 31
32 S61. High Resolution Chemical Ionization Mass Spectra for Compound 3h. S62. High Resolution Chemical Ionization Mass Spectra for Compound 3k. S63. High Resolution Chemical Ionization Mass Spectra for Compound 3m. 32
33 S64. High Resolution Chemical Ionization Mass Spectra for Compound 3o. S65. High Resolution Chemical Ionization Mass Spectra for Compound 3r. 33
34 S66. High Resolution Chemical Ionization Mass Spectra for traces of Compound 3p. 34
35 S67. High Resolution Chemical Ionization Mass Spectra for traces of Compound 3q. S68. High Resolution Chemical Ionization Mass Spectra for Compound 5f. 35
36 S69. High Resolution Chemical Ionization Mass Spectra for Compound 8a. S70. High Resolution Chemical Ionization Mass Spectra for Compound 9a. 36
37 1.3. IR spectra S71. IR spectrum of compound 3a (KBr pellet). S72. IR spectrum of compound 3b (KBr pellet). 37
38 S73. IR spectrum of compound 3d (KBr pellet). S74. IR spectrum of compound 3e (KBr pellet). 38
39 S75. IR spectrum of compound 3f (KBr pellet). S76. IR spectrum of compound 3g (KBr pellet). 39
40 S77. IR spectrum of compound 3h (KBr pellet). S78. IR spectrum of compound 3i (KBr pellet). 40
41 S79. IR spectrum of compound 3j (KBr pellet). S80. IR spectrum of compound 3k (KBr pellet). 41
42 S81. IR spectrum of compound 3m (KBr pellet). S82. IR spectrum of compound 3n(KBr pellet). 42
43 S83. IR spectrum of compound 3o (KBr pellet). S84. IR spectrum of compound 3r(KBr pellet). 43
44 S85. IR spectrum of compound 3s (KBr pellet). S86. IR spectrum of compound 3t (KBr pellet). 44
45 S87. IR spectrum of compound 5a (KBr pellet). S88. IR spectrum of compound 5b (KBr pellet). 45
46 S89. IR spectrum of compound 5c (KBr pellet). S90. IR spectrum of compound 5d (KBr pellet). 46
47 S91. IR spectrum of compound 5e (KBr pellet). S92. IR spectrum of compound 5f (KBr pellet). 47
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