Post on 03-Sep-2020
Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using
Oxone® in aqueous medium as oxidizing agent
Gelson Perin*1, Daniela Rodrigues Araujo1, Patrick Carvalho Nobre1, Eder João Lenardão*1, Raquel Guimarães Jacob1, Márcio Santos Silva2 and Juliano Alex Roehrs3
1 Laboratório de Síntese Orgânica Limpa – LASOL, Universidade Federal de Pelotas – UFPel, Pelotas, RS,
Brazil.2 Centro de Ciências Naturais e Humanas – CCNH, Universidade Federal do ABC – UFABC. Santo André, SP,
Brazil.3 Instituto Federal de Educação Ciência e Tecnologia Sul-rio-grandense – IFSul, Pelotas, RS, Brazil.
*Corresponding authors: lenardao@ufpel.edu.br (E. J. Lenardão) and
gelson_perin@ufpel.edu.br (G. Perin)
Selected Spectra:
Selected Spectra
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
14.35
1.00
0.96
0.0000
7.2325
7.2659
7.2875
7.3002
7.3393
7.3443
7.3628
7.3672
7.3995
7.4131
7.4174
7.4337
7.4706
7.4877
7.4954
7.5149
7.5371
7.6335
7.6552
7.7761
7.7983
7.207.257.307.357.407.457.507.557.607.657.707.757.80
14.351.000.96
7.2325
7.2659
7.2875
7.3002
7.3393
7.3443
7.3628
7.3672
7.3995
7.4131
7.4174
7.4337
7.4706
7.4877
7.4954
7.5149
7.5371
7.6335
7.6552
7.7761
7.7983
Figure 1S. 1H NMR (400 MHz, CDCl3) of the product 3a.
-100102030405060708090100110120130140150160170180190200210
76.6822
77.0000
77.3175
125.4945
126.1071
126.4488
127.8340
127.8648
127.9129
128.1473
128.4750
129.3936
130.1826
130.4960
130.9773
132.1556
133.0909
134.9804
139.6333
139.7074
126128129130131132133135140
125.4945
126.1071
126.4488
127.8340
127.8648
127.9129
128.1473
128.4750
129.3936
130.1826
130.4960
130.9773
132.1556
133.0909
134.9804
139.6333
139.7074
Figure 2S. 13C NMR (100 MHz, CDCl3) of the product 3a.
S2
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
13.41
1.00
0.98
0.0000
7.2376
7.2517
7.2590
7.2657
7.2876
7.3175
7.3212
7.3367
7.3410
7.3591
7.3752
7.3785
7.3916
7.4130
7.4420
7.4619
7.4748
7.4922
7.4965
7.5142
7.5363
7.6656
7.6873
7.8016
7.8218
7.207.257.307.357.407.457.507.557.607.657.707.757.807.85
13.411.000.98
7.2376
7.2517
7.2590
7.2657
7.2876
7.3175
7.3212
7.3367
7.3410
7.3591
7.3752
7.3785
7.3916
7.4130
7.4420
7.4619
7.4748
7.4922
7.4965
7.5142
7.5363
7.6656
7.6873
7.8016
7.8218
Figure 3S. 1H NMR (400 MHz, CDCl3) of the product 3b.
0102030405060708090100110120130140150160170180190200
76.6827
77.0000
77.3175
125.7251
126.1988
126.5836
127.9093
128.2354
128.3436
128.4877
128.9320
129.5742
130.1285
130.3446
132.2962
133.1029
134.1686
136.0223
139.5255
140.1686
126128129130132133134136139140
125.7250
126.1987
126.5835
127.9093
128.2354
128.3436
128.4877
128.9320
129.5742
130.1284
130.3446
132.2962
133.1028
134.1686
136.0223
139.5255
140.1686
Figure 4S. 13C NMR (100 MHz, CDCl3) of the product 3b.
S3
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
2.04
1.01
2.85
2.14
5.21
1.03
1.00
0.0000
6.9797
7.0016
7.0235
7.1740
7.1958
7.3392
7.3430
7.3586
7.3628
7.4034
7.4054
7.4212
7.4250
7.4375
7.4411
7.4781
7.4834
7.4917
7.5000
7.5093
7.5136
7.5272
7.5492
7.6380
7.6598
7.7786
7.7839
7.8016
7.657.757.80
1.031.00
7.6380
7.6598
7.7786
7.7839
7.8016
7.327.367.407.447.487.527.56
2.852.145.21
7.3392
7.3430
7.3586
7.3628
7.4034
7.4054
7.4212
7.4250
7.4375
7.4411
7.4781
7.4834
7.4917
7.5000
7.5093
7.5136
7.5272
7.5492
7.007.057.157.20
2.041.01
6.9797
7.0016
7.0235
7.1740
7.1958
Figure 5S. 1H NMR (400 MHz, CDCl3) of the product 3c.
0102030405060708090100110120130140150160170180190200
76.6831
77.0000
77.3178
116.5737
116.7861
124.6812
124.7161
125.5116
125.9758
126.5350
127.3609
127.8748
127.9225
128.2096
128.5391
130.1397
131.1435
132.0303
133.0156
137.4568
137.5362
139.1812
139.3936
161.6539
164.1199
161163165
161.6539
164.1199
137138139140
137.4568
137.5362
139.1812
139.3936
131132133
131.1435
132.0303
133.0156
127128130
127.3609
127.8748
127.9225
128.2096
128.5391
130.1397
116.5124.5125.5126.5
116.5737
116.7861
124.6812
124.7161
125.5116
125.9758
126.5350
Figure 6S. 13C NMR (100 MHz, CDCl3) of the product 3c.
S4
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
2.90
6.00
1.25
1.97
5.28
4.21
1.02
0.0000
2.3101
2.3698
6.8048
6.8266
6.9888
7.3138
7.3329
7.3516
7.3708
7.3900
7.4167
7.4369
7.5008
7.5162
7.5393
7.5591
7.5762
7.7311
7.7512
6.86.97.07.17.27.37.47.57.67.77.8
1.251.975.284.211.02
6.8048
6.8266
6.9888
7.3138
7.3329
7.3516
7.3708
7.3900
7.4167
7.4369
7.5008
7.5162
7.5393
7.5591
7.5762
7.7311
7.7512
Figure 7S. 1H NMR (400 MHz, CDCl3) of the product 3d.
0102030405060708090100110120130140150160170180190200
21.0725
24.2147
76.6828
77.0000
77.3179
124.8905
125.2084
125.4708
126.3193
127.6958
127.8353
127.8959
128.0117
128.6469
128.8545
130.0309
131.6764
132.0018
133.1936
137.8751
139.0040
139.6756
143.7583
125126128129130132133138139140144
124.8905
125.2084
125.4708
126.3193
127.6958
127.8353
127.8959
128.0117
128.6469
128.8545
130.0309
131.6764
132.0018
133.1936
137.8751
139.0040
139.6756
143.7583
Figure 8S. 13C NMR (100 MHz, CDCl3) of the product 3d.
S5
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
1.06
1.03
2.06
7.51
1.03
1.05
0.99
1.00
0.0000
7.0016
7.0038
7.0138
7.0161
7.0199
7.0223
7.0323
7.0345
7.0930
7.1130
7.2665
7.2715
7.2801
7.2903
7.3491
7.3757
7.3899
7.4001
7.4198
7.4245
7.4649
7.4808
7.5003
7.7165
7.7380
7.7746
7.7962
7.8465
7.8499
7.8692
8.4034
8.4060
8.4154
8.4179
6.957.007.057.107.157.207.257.307.357.407.457.507.707.757.807.857.90
1.061.032.067.511.031.050.99
7.0016
7.0038
7.0138
7.0161
7.0199
7.0223
7.0323
7.0345
7.0930
7.1130
7.2665
7.2715
7.2801
7.2903
7.3491
7.3757
7.3899
7.4001
7.4198
7.4245
7.4649
7.4808
7.5003
7.7165
7.7380
7.7746
7.7962
7.8465
7.8499
7.8692
8.408.45
1.00
8.4034
8.4060
8.4154
8.4179
Figure 9S. 1H NMR (400 MHz, CDCl3) of the product 3e.
0102030405060708090100110120130140150160170180190200
76.6827
77.0000
77.3181
120.7332
126.0264
126.2499
126.4491
126.9594
127.6141
127.6627
127.8636
128.1268
128.4974
129.9699
131.8703
133.0984
133.2946
136.4805
139.9437
143.4963
149.9855
158.1148
120121126127128129130131132133
120.7332
126.0264
126.2499
126.4491
126.9594
127.6141
127.6627
127.8636
128.1268
128.4974
129.9699
131.8703
133.0984
133.2946
135140150
136.4805
139.9437
143.4963
149.9855
158.1148
Figure 10S. 13C NMR (100 MHz, CDCl3) of the product 3e.
S6
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
0.85
1.00
0.98
1.03
2.71
8.45
1.08
1.00
0.99
0.0000
2.5585
2.8665
2.8869
2.8987
2.9191
3.0007
3.0124
3.0330
3.0445
3.4715
3.4863
3.4994
3.5139
3.6340
3.6469
3.6555
3.6750
3.6827
3.6995
3.7139
3.7345
7.2858
7.3046
7.3354
7.3600
7.3901
7.4112
7.4473
7.4556
7.4716
7.4949
7.4992
7.5236
7.5453
7.6587
7.6804
7.7812
7.8027
7.8287
7.8490
7.27.37.47.57.67.77.87.9
8.451.081.000.99
7.2858
7.3046
7.3354
7.3600
7.3901
7.4112
7.4473
7.4556
7.4716
7.4949
7.4992
7.5236
7.5453
7.6587
7.6804
7.7812
7.8027
7.8287
7.8490
3.53.63.73.8
1.032.71
3.4715
3.4863
3.4994
3.5139
3.6340
3.6469
3.6555
3.6750
3.6827
3.6995
3.7139
3.7345
2.93.03.1
1.000.98
2.8665
2.8869
2.8987
2.9191
3.0007
3.0124
3.0330
3.0445
Figure 11S. 1H NMR (400 MHz, CDCl3) of the product 3f.
0102030405060708090100110120130140150160170180190200
31.5457
65.4902
70.2081
76.6825
77.0000
77.3175
125.7976
126.2856
126.6074
127.2426
127.8556
128.2175
128.3688
128.4295
128.4964
130.0116
130.3255
132.3013
133.0222
139.8406
141.6244
125126127128129130131132133140141142
125.7976
126.2856
126.6074
127.2426
127.8556
128.2175
128.3688
128.4295
128.4964
130.0116
130.3255
132.3013
133.0222
139.8406
141.6244
Figure 12S. 13C NMR (100 MHz, CDCl3) of the product 3f.
S7
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.0
0
9.4
51
.07
1.0
22
.00
1.0
00
.99
0.0
00
0
2.4
71
0
7.2
31
57
.24
57
7.2
53
37
.26
58
7.2
88
17
.30
70
7.3
24
57
.34
27
7.3
44
17
.35
43
7.3
57
87
.38
91
7.4
09
57
.41
26
7.4
29
87
.44
30
7.4
64
17
.50
98
7.5
11
87
.51
49
7.5
16
47
.52
96
7.5
33
77
.61
57
7.6
37
77
.76
94
7.7
89
3
7.207.257.307.357.407.457.507.557.607.657.707.757.80f1 (ppm)
9.451.071.022.001.000.99
7.2
31
57
.24
57
7.2
53
37
.26
58
7.2
88
17
.30
70
7.3
24
57
.34
27
7.3
44
17
.35
43
7.3
57
87
.38
91
7.4
09
57
.41
26
7.4
29
87
.44
30
7.4
64
17
.50
98
7.5
11
87
.51
49
7.5
16
47
.52
96
7.5
33
77
.61
57
7.6
37
7
7.7
69
47
.78
93
Figure 13S. 1H NMR (400 MHz, CDCl3) of the product 3g.
0102030405060708090100110120130140150160170180190200
21.4350
76.6824
76.9999
77.3204
125.4022
126.1203
126.3622
127.8350
127.8878
127.9231
128.0051
129.2215
129.3814
129.9839
130.4215
131.1391
132.0841
133.1757
135.0684
136.5469
137.5362
139.5146
129130131132133135136137138139140
129.2215
129.3814
129.9839
130.4215
131.1391
132.0841
133.1757
135.0684
136.5469
137.5362
139.5146
125.5126.0126.5128.0
125.4022
126.1203
126.3622
127.8350
127.8878
127.9231
128.0051
Figure 14S. 13C NMR (100 MHz, CDCl3) of the product 3g.
S8
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
13.22
1.00
1.00
0.0000
7.2693
7.2898
7.3057
7.3139
7.3437
7.3594
7.3765
7.4154
7.4357
7.4729
7.4936
7.6520
7.6738
7.7898
7.8101
7.257.307.357.407.457.507.557.607.657.707.757.807.85
13.221.001.00
7.2693
7.2898
7.3057
7.3139
7.3437
7.3594
7.3765
7.4154
7.4357
7.4729
7.4936
7.6520
7.6738
7.7898
7.8101
Figure 15S. 13C NMR (400 MHz, CDCl3) of the product 3h.
0102030405060708090100110120130140150160170180190200
76.6829
77.0000
77.3179
125.6675
125.7992
126.6601
127.9886
128.0003
128.3599
128.4617
128.7750
129.4523
130.3245
130.9629
131.6380
132.2124
132.9752
133.8656
134.8543
137.9957
138.5595
126128129130131132133134135138
125.6675
125.7992
126.6601
127.9886
128.0003
128.3599
128.4617
128.7750
129.4523
130.3245
130.9629
131.6380
132.2124
132.9752
133.8656
134.8543
137.9957
138.5595
Figure 16S. 13C NMR (100 MHz, CDCl3) of the product 3h.
S9
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0
f1 (ppm)
3.0
0
2.2
1
2.0
0
3.5
15
.49
0.9
41
.00
0.0
00
0
1.0
68
91
.08
73
1.1
05
61
.66
49
1.6
78
71
.68
30
1.6
91
81
.69
69
1.7
02
71
.71
00
1.7
15
31
.72
34
1.7
28
41
.73
38
1.7
42
01
.74
67
1.7
60
63
.30
29
3.3
16
53
.32
33
3.3
29
63
.34
36
7.2
45
27
.26
14
7.2
65
87
.41
67
7.4
25
47
.43
29
7.4
40
67
.45
66
7.4
59
67
.46
28
7.4
76
67
.47
98
7.4
99
87
.50
37
7.5
21
37
.52
43
7.5
43
97
.77
35
7.7
93
68
.04
58
8.0
67
5
7.77.88.08.1f1 (ppm)
0.941.00
7.7
73
57
.79
36
8.0
45
88
.06
75
3.303.35f1 (ppm)
2.00
3.3
02
93
.31
65
3.3
23
33
.32
96
3.3
43
6
1.641.661.681.701.721.741.761.78f1 (ppm)
2.21
1.6
64
91
.67
87
1.6
83
01
.69
18
1.6
96
91
.70
27
1.7
10
01
.71
53
1.7
23
41
.72
84
1.7
33
81
.74
20
1.7
46
71
.76
06
1.051.101.15f1 (ppm)
3.00
1.0
68
91
.08
73
1.1
05
6
7.27.37.47.57.6f1 (ppm)
3.515.49
7.2
45
27
.26
14
7.2
65
87
.41
67
7.4
25
47
.43
29
7.4
40
67
.45
96
7.5
21
37
.52
43
7.5
43
9
Figure 17S. 1H NMR (400 MHz, CDCl3) of the product 3i.
0102030405060708090100110120130140150160170180190200
14.4988
24.1183
34.6359
76.6820
77.0000
77.3178
124.3965
125.6490
126.3505
127.0287
127.0837
127.7075
129.1658
129.2568
129.3133
131.3541
131.5178
131.8488
132.2663
132.8048
133.2476
140.6002
125126127128129131132133141
124.3965
125.6490
126.3505
127.0287
127.0837
127.7075
129.1658
129.2568
129.3133
131.3541
131.5178
131.8488
132.2663
132.8048
133.2476
140.6002
Figure 18S. 13C NMR (100 MHz, CDCl3) of the product 3i.
S10