supporting information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and...
TRANSCRIPT
![Page 1: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/1.jpg)
1
Supporting Information
Synthesis of C2-tetrasubstituted indolin-3-ones via Cu-catalyzed oxidative
dimerization of 2-aryl indoles and cross-addition of indoles
AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band Indresh
Kumar*a
aDepartment of Chemistry, Birla Institute of Technology & Science, Pilani 333 031, India
bDepartment of Chemistry, BITS Pilani, Hyderabad Campus, Secunderabad, India
§authors have contributed equally
Corresponding Email: [email protected], [email protected]
Table of Contents
1H,13C-NMRand HRMS data for the newly synthesized compounds…………….……...…......S2
Single Crystal X-ray and data for 2g…………………………………………………………...S40
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
![Page 2: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/2.jpg)
2
Figure S1: HRMS confirmation of in situ generated 2-phenyl indole-3-one
N
O
Calcd m/z = 208.0762Found m/z = 208.0757
![Page 3: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/3.jpg)
3
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Oct02-2017.3.fidINDO1
1.01
1.03
1.02
1.05
1.04
8.21
1.46
1.04
1.02
1.07
2.02
0.97
6.70
6.72
6.78
6.80
6.81
6.91
6.91
6.92
6.93
6.93
6.94
6.95
6.99
7.01
7.13
7.14
7.15
7.16
7.17
7.18
7.19
7.23
7.24
7.24
7.25
7.27
7.27
7.31
7.33
7.39
7.41
7.42
7.44
7.44
7.44
7.46
7.46
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.4.fidINDO1
72.0
9
110.
7211
2.08
112.
2711
9.19
120.
0012
0.44
121.
5812
2.36
125.
4012
7.25
127.
3912
7.55
127.
6912
8.26
129.
7413
3.26
135.
5513
7.09
137.
1414
0.38
159.
44
200.
34
NH
O
NH2a
NH
O
NH2a
![Page 4: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/4.jpg)
4
NH
O
NH2a
![Page 5: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/5.jpg)
5
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Jun28-2017.2.fidIND-03
0.98
7.62
2.07
1.10
2.14
3.09
0.98
5.20
6.78
6.78
6.80
6.81
6.82
6.83
6.84
6.84
6.86
6.86
6.87
6.88
6.88
6.90
6.90
6.91
6.92
6.92
6.94
6.94
7.03
7.05
7.06
7.07
7.14
7.15
7.16
7.16
7.17
7.18
7.18
7.31
7.33
7.34
7.36
7.36
8.16
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.8.fidINDO3
71.3
9
110.
8811
2.49
112.
6511
4.52
114.
7311
4.95
115.
1611
9.63
120.
2112
0.46
121.
0712
2.61
125.
4112
7.13
128.
9012
8.98
131.
5713
1.66
135.
4813
5.85
135.
8713
6.01
137.
4515
9.26
161.
2016
1.40
163.
6516
3.87
200.
19
NH
O
NH
2bF
F
NH
O
NH
2bF
F
![Page 6: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/6.jpg)
6
NH
O
NH
2bF
F
![Page 7: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/7.jpg)
7
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Nov18-2017.1.fidInd09
0.87
2.05
1.97
5.38
2.08
1.15
1.32
1.03
2.19
1.01
5.21
6.86
6.87
6.88
6.89
6.90
6.94
6.95
7.02
7.03
7.05
7.07
7.10
7.10
7.10
7.12
7.12
7.12
7.15
7.16
7.17
7.19
7.19
7.20
7.21
7.21
7.21
7.32
7.34
7.36
7.37
7.37
7.38
7.39
7.39
7.45
7.46
7.50
7.51
7.52
7.53
7.54
7.54
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov18-2017.2.fidInd09
71.3
7
111.
0211
2.37
112.
6812
0.08
120.
4212
0.43
120.
9612
2.88
125.
4812
5.80
126.
9812
7.14
127.
7412
7.80
128.
4412
8.89
129.
4612
9.96
133.
6413
4.07
134.
5013
5.57
135.
9313
7.73
141.
9315
9.33
199.
90
NH
O
NH2c
Cl
Cl
NH
O
NH2c
Cl
Cl
![Page 8: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/8.jpg)
8
NH
O
NH2c
Cl
Cl
![Page 9: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/9.jpg)
9
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Nov22-2017/1Ind06
1.00
1.87
2.00
1.91
1.86
2.92
2.13
1.94
1.23
1.00
5.20
6.85
6.86
6.87
6.87
6.89
6.91
6.93
6.95
6.97
6.99
7.03
7.05
7.12
7.14
7.17
7.19
7.20
7.22
7.35
7.37
7.39
7.41
7.46
7.49
7.52
7.53
7.54
7.54
8.14
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov22-2017/3Ind06
71.4
0
110.
9211
2.52
119.
7812
0.35
120.
4912
1.07
122.
7812
5.46
127.
1112
7.84
128.
3912
8.65
131.
0613
1.22
132.
0213
3.68
134.
5913
5.55
135.
8113
7.54
138.
6815
9.25
199.
76
NH
O
NH
2dCl
Cl
NH
O
NH
2dCl
Cl
![Page 10: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/10.jpg)
10
NH
O
NH
2dCl
Cl
![Page 11: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/11.jpg)
11
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Oct02-2017.5.fidINDO2
1.00
2.10
2.01
2.22
1.10
2.07
1.40
2.26
1.07
1.06
1.10
1.00
1.01
5.25
6.90
6.91
6.92
6.93
6.96
6.97
7.00
7.02
7.04
7.06
7.10
7.12
7.17
7.19
7.20
7.21
7.26
7.27
7.27
7.33
7.35
7.35
7.36
7.38
7.43
7.45
7.47
7.49
7.53
7.53
7.55
7.56
7.57
7.70
7.71
7.71
8.27
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct02-2017.6.fidINDO2
71.3
1
111.
0411
2.35
112.
7112
0.13
120.
3812
0.43
120.
9312
1.82
122.
3412
2.87
125.
5012
6.29
126.
9312
8.18
129.
0912
9.73
129.
9813
0.72
131.
3113
2.79
134.
7513
5.57
135.
9213
7.76
142.
1115
9.34
199.
95
NH
O
NH2e
Br
Br
NH
O
NH2e
Br
Br
![Page 12: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/12.jpg)
12
NH
O
NH2e
Br
Br
![Page 13: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/13.jpg)
13
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec23-2017/1IND-15
0.98
0.98
0.99
2.03
6.86
1.25
1.98
2.12
0.98
5.13
6.57
6.59
7.04
7.04
7.12
7.13
7.15
7.18
7.20
7.21
7.22
7.23
7.23
7.23
7.24
7.25
7.29
7.29
7.30
7.31
7.33
7.33
7.33
7.41
7.42
7.43
7.43
7.48
7.50
7.51
8.15
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec23-2017/2IND-15
72.5
5
111.
2311
1.45
112.
1711
3.34
113.
7312
1.74
124.
0712
5.43
127.
0612
7.73
127.
9012
8.10
128.
5912
8.77
128.
9412
9.65
132.
6513
4.10
138.
1513
9.51
139.
7215
7.52
198.
61
NH
O
NH
Br
Br
2f
NH
O
NH
Br
Br
2f
![Page 14: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/14.jpg)
14
NH
O
NH
Br
Br
2f
![Page 15: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/15.jpg)
15
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Nov15-2017.1.fidINDO8
3.20
3.11
1.00
0.97
1.04
8.05
1.06
1.02
2.95
1.02
0.96
2.27
2.33
5.17
6.67
6.69
6.76
6.78
6.80
6.91
6.92
6.95
6.99
7.01
7.02
7.04
7.11
7.13
7.15
7.27
7.29
7.35
7.37
7.39
7.41
7.41
7.43
7.45
7.45
8.10
6.66.76.86.97.07.17.27.37.47.5f1 (ppm)
0.97
1.04
8.05
1.06
1.02
2.95
1.02
6.67
6.69
6.76
6.78
6.80
6.91
6.92
6.95
6.99
7.01
7.02
7.04
7.11
7.13
7.15
7.27
7.29
7.35
7.37
7.39
7.41
7.41
7.43
7.45
7.45
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov15-2017.2.fidINDO8
21.0
221
.23
71.9
3
110.
6211
1.82
112.
1111
8.88
119.
7712
0.39
121.
6112
2.10
125.
3312
7.10
127.
4812
8.32
128.
9312
9.52
130.
3113
5.45
136.
9313
7.00
137.
1313
7.46
137.
9915
9.14
200.
49
NH
O
NH
H3C
CH3
2g
NH
O
NH
H3C
CH3
2g
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16
NH
O
NH
H3C
CH3
2g
![Page 17: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/17.jpg)
17
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Nov24-2017/2IND-10
2.99
3.02
0.99
0.97
2.00
2.95
1.08
6.39
1.16
2.10
0.99
3.56
3.67
5.20
6.64
6.64
6.64
6.69
6.70
6.71
6.71
6.74
6.78
6.79
6.80
6.81
6.82
6.83
6.92
6.94
6.95
7.05
7.07
7.08
7.09
7.10
7.11
7.13
7.15
7.17
7.31
7.33
7.42
7.42
7.44
7.45
7.47
7.47
8.101
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
Nov25-2017/1ind-10
54.9
455
.17
71.9
8
110.
6711
1.70
112.
2111
2.88
113.
1911
4.71
114.
7711
9.21
119.
7412
0.05
120.
4212
1.50
121.
7512
2.38
125.
3812
7.35
128.
8312
9.19
134.
5713
5.41
136.
9913
7.12
141.
9015
8.68
159.
2115
9.38
200.
10
NH
O
NH
OCH3
H3CO
2h
NH
O
NH
OCH3
H3CO
2h
![Page 18: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/18.jpg)
18
NH
O
NH
OCH3
H3CO
2h
![Page 19: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/19.jpg)
19
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Jan15-2018/1IND17
3.03
3.07
1.02
2.10
3.07
1.17
1.17
1.14
2.06
1.10
1.07
4.22
1.00
3.73
3.77
5.18
6.64
6.66
6.71
6.71
6.72
6.73
6.73
6.74
6.76
6.78
6.80
6.90
6.90
6.92
6.92
6.94
6.94
6.97
6.99
7.01
7.03
7.11
7.11
7.13
7.13
7.13
7.15
7.15
7.29
7.31
7.38
7.39
7.41
7.43
7.43
7.44
7.45
7.45
8.07
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Jan15-2018/2IND17
55.2
455
.31
71.6
5
110.
6311
2.19
112.
2411
3.13
113.
6711
9.03
119.
8912
0.53
121.
5012
2.15
125.
4212
5.50
127.
5112
8.44
130.
9713
2.47
135.
4313
6.84
137.
03
159.
0815
9.17
159.
50
200.
67
NH
O
NH
2iH3CO
OCH3
NH
O
NH
2iH3CO
OCH3
![Page 20: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/20.jpg)
20
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec16-2017/2IND13
3.09
3.17
2.96
3.23
1.12
1.91
1.98
1.00
1.00
2.05
1.98
1.99
1.11
2.16
2.16
2.21
2.30
2.31
4.94
6.65
6.68
6.93
6.95
7.11
7.16
7.24
7.25
7.28
7.35
7.37
7.85
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec27-2017/2IND 13
19.2
520
.35
21.3
1
71.7
5
111.
1711
2.12
113.
4011
8.86
121.
0012
1.56
122.
4412
5.02
125.
4912
6.31
128.
9312
9.01
130.
6013
1.11
131.
3213
1.99
132.
0313
4.57
134.
9113
9.78
148.
21
158.
56
199.
34
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
![Page 21: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/21.jpg)
21
NH
O
NH
H3C
H3CCH3
CH3
Br
Br 2j
![Page 22: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/22.jpg)
22
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Jul17-2019/1MEINDOLE
2.92
2.77
0.98
2.08
1.03
0.99
1.04
1.06
1.05
1.05
1.00
1.95
2.45
5.05
6.89
6.89
6.91
6.91
6.91
6.92
6.93
6.96
6.96
6.98
6.98
6.98
7.00
7.00
7.07
7.08
7.09
7.09
7.10
7.11
7.11
7.25
7.25
7.25
7.27
7.27
7.27
7.41
7.41
7.43
7.43
7.52
7.52
7.53
7.54
7.54
7.55
7.56
7.72
7.72
7.74
7.74
7.90
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Jul19-2019/2INDME
14.5
9
25.0
9
67.1
4
109.
5111
0.43
111.
4911
2.45
119.
0811
9.50
119.
7612
1.27
125.
3212
7.45
132.
5913
4.90
137.
47
159.
55
204.
31
NH
OCH3
NH2k H3C
NH
OCH3
NH2k H3C
![Page 23: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/23.jpg)
23
NH
OCH3
NH2k H3C
![Page 24: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/24.jpg)
24
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec12-2017/2INDOLE 4F
0.92
5.10
3.21
1.08
2.96
1.00
0.95
5.36
6.91
6.93
6.94
6.95
6.96
6.98
7.00
7.02
7.03
7.05
7.05
7.15
7.17
7.18
7.19
7.20
7.20
7.22
7.23
7.24
7.40
7.42
7.51
7.52
7.54
7.54
7.56
7.56
7.58
7.71
7.73
8.20
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec12-2017/4INDOLE 4F
70.7
4
111.
7111
3.09
115.
1411
5.35
115.
5311
9.58
119.
9212
0.20
122.
7112
3.60
125.
4612
5.66
128.
5612
8.65
135.
3113
6.96
137.
65
160.
51
200.
35
NH
O
NH
F
4ab
NH
O
NH
F
4ab
![Page 25: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/25.jpg)
25
NH
O
NH
F
4ab
![Page 26: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/26.jpg)
26
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Dec16-2017/1INDOLE4CL
0.98
2.02
1.04
2.01
1.06
2.33
1.00
2.99
1.00
0.97
5.35
6.89
6.91
6.93
6.98
6.98
7.00
7.02
7.02
7.12
7.12
7.13
7.13
7.17
7.17
7.19
7.21
7.21
7.24
7.25
7.26
7.26
7.36
7.38
7.49
7.51
7.53
7.53
7.68
7.70
8.26
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec16-2017/3INDOLE4CL
70.7
8
111.
7411
3.11
115.
1511
9.45
119.
4611
9.95
120.
1712
2.68
123.
6512
5.34
125.
6012
8.29
128.
5213
3.66
136.
9013
7.70
138.
13
160.
54
200.
16
NH
O
NH
Cl
4ad
NH
O
NH
Cl
4ad
![Page 27: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/27.jpg)
27
NH
O
NH
Cl
4ad
![Page 28: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/28.jpg)
28
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Oct16-2017/1INDOLE3 Br
0.99
2.06
1.06
4.01
2.08
1.00
1.01
1.00
0.94
0.96
5.38
6.92
6.92
6.94
6.94
6.95
6.96
6.97
7.01
7.01
7.03
7.03
7.03
7.05
7.05
7.15
7.16
7.17
7.19
7.21
7.21
7.23
7.23
7.39
7.41
7.41
7.41
7.42
7.43
7.43
7.43
7.44
7.49
7.49
7.49
7.51
7.51
7.51
7.52
7.52
7.54
7.54
7.54
7.56
7.56
7.71
7.73
7.81
7.81
7.82
8.30
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct16-2017/2INDOLE3 Br
70.7
6
111.
8011
3.25
115.
0811
9.41
119.
4812
0.07
120.
2612
2.59
122.
7412
3.79
125.
3512
5.66
126.
0612
9.45
130.
0513
0.87
136.
9513
7.80
142.
01
160.
56
199.
92
NH
O
NH4ae
Br
NH
O
NH4ae
Br
![Page 29: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/29.jpg)
29
NH
O
NH4ae
Br
![Page 30: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/30.jpg)
30
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec07-2017/1INDOLE4CH3
3.05
0.94
2.15
1.09
3.11
2.21
1.13
2.07
1.08
1.02
0.98
2.31
5.39
6.86
6.86
6.88
6.89
6.91
6.96
6.96
6.98
7.00
7.00
7.09
7.10
7.11
7.11
7.14
7.14
7.16
7.16
7.17
7.18
7.18
7.19
7.33
7.35
7.42
7.44
7.47
7.47
7.49
7.49
7.49
7.51
7.51
7.68
7.69
8.29
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec08-2017/1INDOLE4CH3
31.6
3
71.2
4
111.
7011
2.87
115.
5011
9.54
119.
5911
9.82
119.
9712
2.45
123.
8312
5.62
125.
6812
6.72
129.
2213
6.52
136.
9813
7.46
137.
54
160.
58
200.
96
CH3
NH
O
NH4ag
CH3
NH
O
NH4ag
![Page 31: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/31.jpg)
31
CH3
NH
O
NH4ag
![Page 32: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/32.jpg)
32
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
Oct14-2017/1INDOLE2OH
1.29
0.96
6.47
1.11
1.18
2.43
1.06
1.02
1.01
0.98
2.08
5.42
6.90
6.91
6.93
6.94
6.95
6.96
6.96
6.98
6.98
6.99
7.01
7.08
7.10
7.12
7.13
7.14
7.16
7.16
7.24
7.25
7.26
7.26
7.27
7.29
7.56
7.56
7.58
7.58
7.59
7.60
7.60
7.70
7.70
7.72
7.72
7.75
7.77
8.39.
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Oct14-2017/2INDOLE2OH
71.6
2
111.
8711
3.44
113.
7811
8.81
119.
0812
0.15
120.
2512
0.70
122.
5812
4.06
124.
5712
4.96
125.
6912
8.18
129.
9613
6.89
138.
71
156.
08
160.
12
171.
36
204.
04
NH
O
NH
HO
4ak
NH
O
NH
HO
4ak
![Page 33: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/33.jpg)
33
NH
O
NH
HO
4ak
![Page 34: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/34.jpg)
34
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec01-2017/1INDOLE8
3.00
0.92
0.99
1.01
0.99
0.96
1.00
4.53
1.04
2.00
1.02
0.99
3.63
5.39
6.57
6.58
6.83
6.84
6.86
6.86
6.90
6.92
6.94
6.95
6.97
7.11
7.12
7.26
7.28
7.29
7.30
7.31
7.32
7.34
7.51
7.52
7.53
7.55
7.55
7.61
7.61
7.63
7.63
7.71
7.73
8.14
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec01-2017/4INDOLE8
55.5
9
71.2
7
101.
8611
2.27
112.
3111
2.88
115.
4711
9.64
119.
7712
4.46
125.
5112
6.04
126.
8412
7.72
128.
4013
1.99
137.
5213
9.35
154.
02
160.
54
200.
71
NH
O
NH4ba
OCH3
NH
O
NH4ba
OCH3
![Page 35: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/35.jpg)
35
NH
O
NH4ba
OCH3
![Page 36: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/36.jpg)
36
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
Dec01-2017/2INDOLE9
2.94
1.04
1.02
1.04
4.04
1.03
1.41
3.10
1.01
1.00
3.65
5.37
6.55
6.55
6.84
6.85
6.86
6.87
6.91
6.93
6.95
6.97
6.98
7.00
7.03
7.09
7.09
7.26
7.28
7.52
7.52
7.54
7.55
7.57
7.58
7.59
7.60
7.71
7.73
8.19
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec01-2017/3INDOLE9 55
.66
70.7
9
101.
77
112.
3711
2.43
113.
1011
5.12
115.
2811
5.33
119.
7011
9.93
124.
4112
5.58
125.
9112
8.65
128.
7313
2.05
135.
1613
7.70
154.
13
160.
5916
1.30
163.
74
200.
64
NH
O
NH4bb
OCH3
F
NH
O
NH4bb
OCH3
F
![Page 37: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/37.jpg)
37
NH
O
NH4bb
OCH3
F
![Page 38: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/38.jpg)
38
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
Dec21-2017/1INDOLEDM
3.00
3.03
0.99
0.96
1.94
1.04
1.00
0.95
2.18
1.12
0.91
1.12
1.00
1.00
3.62
3.74
5.32
6.58
6.59
6.80
6.81
6.82
6.82
6.83
6.84
6.87
6.89
6.91
6.92
6.94
7.11
7.11
7.17
7.18
7.18
7.19
7.19
7.21
7.23
7.24
7.25
7.27
7.48
7.48
7.50
7.50
7.52
7.52
7.68
7.70
8.01
0102030405060708090100110120130140150160170180190200210f1 (ppm)
Dec23-2017/3INDOLEEDM
55.2
455
.65
71.1
4
101.
91
112.
2211
2.32
112.
8411
2.88
112.
9311
5.51
119.
3411
9.66
119.
8212
4.46
125.
5312
6.07
129.
3713
1.97
137.
4914
1.02
154.
0915
9.63
160.
48
200.
41
NH
O
NH4bh
OCH3
H3CO
NH
O
NH4bh
OCH3
H3CO
![Page 39: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/39.jpg)
39
NH
O
NH4bh
OCH3
H3CO
![Page 40: Supporting Information dimerization of 2-aryl indoles and ... · dimerization of 2-aryl indoles and cross-addition of indoles AnoopSingh,a§SatheeshvarmaVanaparthi,a§SachinChoudhary,aRanganKrishnan,band](https://reader030.vdocuments.mx/reader030/viewer/2022040107/5ea22301e7d6870d1e338965/html5/thumbnails/40.jpg)
40
Crystal structure data for (2g):
Crystal structure of 2-(p-tolyl)-2-(2-(p-tolyl)-1H-indol-3-yl)indolin-3-one(2g):
(CCDC No.1832862)
Single crystals of2-(p-tolyl)-2-(2-(p-tolyl)-1H-indol-3-yl)indolin-3-
oneC61H49Cl3N4O2was selected on aXtaLAB Pro: Kappa dual
offset/far diffractometer. The crystal was kept at 93(2) K during data
collection. Using Olex2,[1] the structure was solved with the ShelXT[2]
structure solution program using Intrinsic Phasing and refined with theShelXL[3] refinement
package using Least Squares minimization.
Crystal Data for C61H49Cl3N4O2 (M =976.39 g/mol): triclinic, space group P-1 (no. 2), a =
13.13930(10) Å, b = 14.65600(10) Å, c = 15.47680(10) Å, α = 110.2300(10)°, β = 91.2620(10)°,
γ = 108.1490(10)°, V = 2629.10(4) Å3, Z = 2, T = 93(2) K, μ(CuKα) = 1.943 mm-1, Dcalc =
1.233 g/cm3, 28497 reflections measured (7.156° ≤ 2Θ ≤ 149.04°), 10338 unique (Rint = 0.0246,
Rsigma = 0.0226) which were used in all calculations. The final R1 was 0.0623 (I >2σ(I)) and wR2
was 0.1867 (all data).
TableS1:Crystal structure data of (2g): (CCDC No.1832862)
Table 1 Crystal data and structure refinement for exp_255-IND8a.
Identification code CCDC No.1832862
Empirical formula C61H49Cl3N4O2
Formula weight 976.39
Temperature/K 93(2)
Crystal system triclinic
NH
O
NH
H3C
CH3
2g
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Space group P-1
a/Å 13.13930(10)
b/Å 14.65600(10)
c/Å 15.47680(10)
α/° 110.2300(10)
β/° 91.2620(10)
γ/° 108.1490(10)
Volume/Å3 2629.10(4)
Z 2
ρcalcg/cm3 1.233
μ/mm-1 1.943
F(000) 1020.0
Crystal size/mm3 0.2 × 0.2 × 0.1
Radiation CuKα (λ = 1.54184)
2Θ range for data collection/° 7.156 to 149.04
Index ranges -15 ≤ h ≤ 16, -18 ≤ k ≤ 18, -19 ≤ l ≤ 13
Reflections collected 28497
Independent reflections 10338 [Rint = 0.0246, Rsigma = 0.0226]
Data/restraints/parameters 10338/0/635
Goodness-of-fit on F2 1.069
Final R indexes [I>=2σ (I)] R1 = 0.0623, wR2 = 0.1847
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Final R indexes [all data] R1 = 0.0645, wR2 = 0.1867
Largest diff. peak/hole / e Å-3 0.49/-0.84
FigureS2 Single crystal X-ray of 2g(CCDC No.1832862). The thermal ellipsoids are drawn at
the 50% probability level. The compound was crystalized with CHCl3.
References:
1. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. &Puschmann, H. (2009), J.
Appl. Cryst. 42, 339-341.
2. Sheldrick, G.M. (2015). ActaCryst. A71, 3-8.
3. Sheldrick, G.M. (2015). ActaCryst. C71, 3-8.
NH
O
NH
H3C
CH3
2g