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