Supporting Information - Royal Society of Chemistry

Electronic Supplementary Material (ESI) for Dalton Transactions.
This journal is © The Royal Society of Chemistry 2016
Supporting Information
Dialkylboron Guanidinates: Syntheses, Structures and Carbodiimide
De-insertion Reactions
Antonio Antiñolo,*a Fernando Carrillo-Hermosilla,a Rafael Fernández-Galán,a María Pilar MonteroRama,a Alberto Ramos,*b Elena Villaseñor,a Rene S. Rojasc and Antonio Rodríguez-Diéguezd
Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Inorgánica, Orgánica y
Bioquímica, Facultad de Ciencias y Tecnologías Químicas, Universidad de Castilla-La Mancha, Campus Universitario,
E-13071 Ciudad Real, Spain.
a
b Centro de Innovación en Química Avanzada (ORFEO-CINQA), Departamento de Química Inorgánica, Orgánica y
Bioquímica, Instituto Regional de Investigación Científica Aplicada, Universidad de Castilla-La Mancha, Campus
Universitario, E-13071 Ciudad Real, Spain.
c Pontificia Universidad Católica de Chile. Facultad de Química, Vicuña Makenna 4860, Casilla 306, Correo 22,
Santiago de Chile.
d Departamento
de Química Inorgánica, Facultad de Ciencias, Universidad de Granada, Avenida de la Fuente Nueva
S/N, 18071 Granada, Spain.
S1
Table S1. Equilibrium constants (Keq) for the carbodiimide de-insertion reaction of
[10][𝐷𝐼𝐶]
𝐾𝑒𝑞 =
[1]
compound 1 at different temperatures in toluene-d8. (
; [1]0 = 5.70·10-2
M).
T (ºC)
25
50
60
70
80
[1] (M)
3.31·10-2
1.97·10-2
8.84·10-3
6.50·10-3
3.39·10-3
[10] = [DIC] (M)
2.39·10-2
3.73·10-2
4.82·10-2
5.05·10-2
5.36·10-2
Keq (M)
1.73·10-2
7.06·10-2
2.63·10-1
3.93·10-1
8.49·10-1
Table S2. Rate constants (k1) for the carbodiimide de-insertion reaction of compound 1
at different temperatures in toluene-d8.
T (ºC)
25
50
60
70
80
k1 (s-1)
1.83(2)·10-6
2.51(3)·10-5
1.31(3)·10-4
3.8(1)·10-4
9.0(4)·10-4
S2
Figure S1. Van’t Hoff plot (ln Keq vs 1/T) for the carbodiimide de-insertion reaction of
compound 1 (H° = 63(6) KJ mol-1, S° = 175(18) J mol-1 K-1).
Van’t Hoff equation:
ln K𝑒𝑞 =
‒ ∆𝐻° 1
∆𝑆°
+
𝑅
𝑇
𝑅
()
S3
S4
S5
Figure S2. First order rate plot (ln [1] vs t) for the carbodiimide de-insertion reaction of
compound 1 at (a) 25 ºC, (b) 50 ºC, (c) 60 ºC, (d) 70 ºC, (e) 80 ºC.
1
k1
k-1
10 + CDI
Assuming: k-1[10][CDI] << k1[1],
ln [1] = ln [1]0 – k1t
S6
Figure S3. Arrhenius plot (ln k1 vs 1/T) for the carbodiimide de-insertion reaction of
compound 1 (Ea = 101(5) KJ mol-1).
Arrhenius equation:
ln 𝑘1 =
‒ 𝐸𝑎 1
+ ln 𝐴
𝑅 𝑇
()
S7
Figure S4. Eyring plot (ln k1/T vs 1/T) for the carbodiimide de-insertion reaction of
compound 1 (H‡ = 98(5) KJ mol-1, S‡ = 27(16) J mol-1 K-1).
Eyring equation:
ln
𝑘1
()
𝑇
=
𝑘𝐵
‒ ∆𝐻 ‡ 1
∆𝑆 ‡
+
+ ln
𝑅
𝑇
𝑅
ℎ
()
()
S8
180
i
N
i
170
6.5
N
C
B
N
160
150
6.0
140
2.25
5.5
130
2.20
120
2.15
5.0
50
1.20
4.5
Pr
48
110
1.15
S9
1.10
f1 (ppm)
4.0
3.5
f1 (ppm)
46
44
100
90
f1 (ppm)
42
40
80
1.05
3.0
38
70
2.5
36
34
f1 (ppm)
60
32
50
6.05
3.24
12.53
3.51
3.00
11.44
2.87
2.96
2.35 2.30
f1 (ppm)
2.80
2.10
8.37
0.96
3.09
N
2.0
30
40
23.835
23.753
23.240
23.119
45.372
45.236
45.100
39.950
39.791
38.597
38.541
38.290
38.241
38.064
36.382
36.250
34.865
34.823
33.668
30.165
30.065
23.835
23.753
23.240
23.119
7.0
2.40
30.165
30.065
(b)
2.45
39.950
39.791
38.597
38.541
38.290
38.241
38.064
36.382
36.250
34.865
34.823
33.668
2.50
45.372
45.236
45.100
7.5
160.228
1.171
1.157
1.133
1.127
1.120
1.114
1.082
1.068
2.179
2.275
2.235
2.230
2.465
1.771
1.615
1.538
1.519
1.501
1.275
1.171
1.157
1.133
1.127
1.120
1.114
1.082
1.068
3.355
3.342
3.329
3.316
3.303
3.289
3.276
3.263
3.255
3.250
3.241
3.228
3.215
2.465
2.275
2.235
2.230
2.179
(a)
i
i
28
30
Pr
N
C
B
1.5
1.0
26
24
20
Nrb
N
Nrb
Pr
1.00
0.5
22
10
0.0
Nrb
Nrb
Pr
20
0
9.339
(c)
i
Pr
N
N
C
B
N
i
100
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
Nrb
Nrb
Pr
-60
-70
-80
-90
-100
Figure S5. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 1 (diastereomer
mixture).
S10
N
180
170
6.5
N
C
B
N
160
150
6.0
140
5.5
56
130
120
2.5
5.0
4.5
54
110
52
100
2.4
50
2.3
4.0
f1 (ppm)
48
90
f1 (ppm)
S11
3.5
46
80
3.0
44
70
2.5
42
40
f1 (ppm)
60
2.0
38
50
36
40
1.15
2.7
2.6
f1 (ppm)
22.13
2.8
1.20
3.00
0.65
0.63
N
C
1.5
1.0
34
32
30
30
20
26.884
26.556
7.0
2.9
39.993
39.772
38.771
38.758
38.462
38.131
38.114
34.857
34.287
33.683
26.884
26.818
26.752
26.599
26.556
7.5
55.161
55.001
54.737
1.39
3.0
39.993
39.772
38.771
38.758
38.462
38.442
38.131
38.114
36.598
36.504
35.429
34.964
34.857
34.340
34.287
33.839
33.683
30.077
30.034
55.161
55.001
54.737
(b)
160.064
3.1
2.193
2.299
2.297
2.255
2.464
3.059
3.051
3.042
3.030
3.022
2.998
2.989
2.981
2.969
2.961
2.952
2.941
2.933
2.924
(a)
Cy
N
B
Nrb
N
Nrb
Cy
2.2
0.5
28
10
0.0
Cy
Nrb
Nrb
Cy
26
0
3.022
2.998
2.989
2.981
2.961
2.464
2.299
2.297
2.255
2.193
1.985
1.964
1.943
1.899
1.857
1.754
1.744
1.738
1.706
1.677
1.673
1.655
1.651
1.587
1.564
1.539
1.526
1.513
1.505
1.499
1.484
1.455
1.425
1.419
1.286
1.265
1.200
1.186
1.181
1.168
1.161
1.154
1.136
1.129
1.122
1.114
1.109
1.098
1.080
1.073
1.048
0.981
0.961
0.940
(c)
Cy
N
N
C
B
N
Nrb
Nrb
Cy
Figure S6. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 2 (diastereomer
mixture).
S12
(b)
N
170
160
7.5
7.0
i
C
N
i
150
N
B
6.5
140
2.4
6.0
130
2.2
2.0
f1 (ppm)
5.5
5.0
46
120
44
42
110
1.8
40
100
1.6
4.5
38
1.4
S13
1.2
36
34
f1 (ppm)
90
80
f1 (ppm)
1.0
4.0
3.5
f1 (ppm)
3.0
32
30
70
2.5
28
26
60
2.0
50
1.5
40
30
2.00
2.6
11.05
2.8
24.58
3.0
30.761
29.769
29.489
28.842
23.883
8.0
3.2
39.083
N
44.815
3.4
B
4.98
3.6
C
23.883
1.96
N
30.761
29.769
29.489
28.842
i
39.083
i
44.815
N
158.169
0.832
0.809
0.802
1.270
1.245
1.130
1.114
2.009
2.003
1.980
1.917
1.885
1.882
1.532
1.501
1.495
1.479
2.315
3.448
3.432
3.415
3.399
3.382
3.366
3.349
1.532
1.501
1.495
1.479
1.270
1.260
1.245
1.130
1.114
0.832
0.809
0.802
0.796
2.315
2.009
2.003
1.980
1.917
1.885
1.882
3.448
3.432
3.415
3.399
3.382
3.366
3.349
(a)
Pr
Cy
Cy
Pr
0.8
1.0
0.5
20
0.0
Pr
Cy
Cy
Pr
24
10
0
9.252
(c)
i
Pr
N
N
C
B
N
i
100
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
Cy
Pr
-60
Figure S7. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 3.
S14
Cy
-70
-80
-90
-100
N
6.5
C
190
6.0
(b)
N
B
N
180
170
160
1.9
f1 (ppm)
5.5
150
1.7
5.0
140
1.5
4.5
130
1.3
4.0
f1 (ppm)
55
120
S15
1.1
3.5
50
110
3.0
45
2.5
100
90
f1 (ppm)
2.0
40
f1 (ppm)
80
35
70
2.43
2.1
1.5
30
60
39.280
34.735
30.841
29.818
29.693
28.867
26.609
26.266
7.0
2.3
54.164
2.5
51.11
N
30.841
29.818
29.693
28.867
26.609
26.266
7.5
2.7
34.735
2.9
5.72
2.00
3.1
39.280
54.164
8.0
158.001
3.133
3.117
3.110
3.103
3.087
2.364
2.044
2.021
1.999
1.978
1.930
1.926
1.904
1.900
1.712
1.706
1.685
1.680
1.536
1.513
1.506
1.388
1.364
1.339
1.165
1.139
1.133
1.113
1.085
1.060
1.035
0.893
0.888
0.873
0.869
0.845
2.021
1.999
1.978
1.930
1.926
1.904
1.900
1.706
1.685
1.680
1.536
1.513
1.506
1.364
1.165
1.139
3.140
3.133
3.126
3.117
3.110
3.103
3.094
3.087
3.080
2.364
(a)
Cy
N
C
B
1.0
50
Cy
N
Cy
Cy
0.9
0.5
40
0.0
Cy
Cy
Cy
Cy
25
30
20
10
0
9.465
(c)
Cy
N
N
C
B
N
Cy
Cy
Cy
100
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
-60
Figure S8. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 4.
S16
-70
-80
-90
-100
N
C
180
N
B
N
170
160
150
5.0
140
4.5
130
38.551
38.140
31.080
29.753
28.491
27.988
25.107
24.686
5.5
39
120
4.0
f1 (ppm)
38
110
S17
1.8
37
1.6
3.5
36
100
1.4
3.0
35
34
90
f1 (ppm)
1.2
2.5
2.0
33
32
31
f1 (ppm)
80
70
30
60
10.86
2.0
19.20
2.4
2.2
f1 (ppm)
14.82
2.6
5.25
4.00
N
1.5
29
28
50
25.107
24.686
(b)
2.8
28.491
27.988
6.0
3.0
29.753
6.5
3.2
31.080
38.551
38.140
7.0
3.4
126.633
124.613
7.5
3.6
139.757
3.8
146.038
8.0
159.381
5.86
1.447
1.426
1.405
1.388
1.169
1.152
1.977
1.846
1.842
1.818
1.794
1.700
1.672
3.725
3.708
3.691
3.674
3.657
3.640
3.623
1.977
1.846
1.842
1.818
1.794
1.700
1.672
1.447
1.426
1.405
1.388
1.339
1.323
1.306
1.169
1.152
3.725
3.708
3.691
3.674
3.657
3.640
3.623
7.098
7.093
7.089
(a)
DIPP
N
C
B
1.0
27
26
40
Cy
N
Cy
DIPP
1.0
0.5
0.0
DIPP
Cy
Cy
DIPP
25
30
24
20
10
0
13.842
(c)
DIPP
N
N
C
B
N
Cy
Cy
DIPP
100
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
-60
Figure S9. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 5.
S18
-70
-80
-90
-100
i
Pr
H
N
180
C
N
i
Pr
6.5
170
N
B
6.0
160
Cy
Cy
150
5.5
140
130
120
B
N
i
3.5
3.4
3.3
f1 (ppm)
5.0
4.5
4.0
f1 (ppm)
32
110
Ph
S19
3.2
30
100
3.1
3.5
3.0
90
f1 (ppm)
2.5
28
26
f1 (ppm)
80
24
70
11.09
6.00
2.52
6.18
C
10.40
N
2.0
1.5
60
50
30.523
30.251
29.568
29.249
28.602
23.423
23.401
7.0
1.31
1.07
1.31
H
N
45.431
44.241
7.5
3.6
Pr
121.539
121.436
8.0
3.7
129.051
3.8
143.717
i
23.423
23.401
30.523
30.251
29.568
29.249
28.602
(b)
153.659
8.5
1.13
4.84
3.480
3.464
3.454
3.449
3.438
3.433
3.422
3.406
3.272
3.246
3.184
3.168
3.152
3.135
3.119
(a)
Ph
Cy
Cy
Pr
3.0
1.0
0.5
40
0.0
22
30
20
10
0
7.173
7.169
7.160
7.155
7.151
6.863
6.854
6.850
6.844
6.841
6.838
6.833
6.828
6.820
3.480
3.464
3.454
3.449
3.438
3.422
3.406
3.272
3.246
3.168
3.152
3.135
3.119
2.027
1.999
1.949
1.916
1.892
1.523
1.516
1.485
1.456
1.428
1.406
1.365
1.359
1.344
1.100
1.083
1.012
1.006
0.999
0.982
0.976
0.970
0.952
0.946
0.940
0.700
0.684
12.046
(c)
Ph
i
Pr
H
N
N
C
55
50
45
40
35
30
25
20
15
10
5
0
f1 (ppm)
-5
-10
-15
-20
-25
-30
Pr
-35
-40
Figure S10. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 6.
S20
Cy
N
i
60
Cy
B
-45
-50
-55
-60
i
Pr
H
N
i
C
N
Pr
6.5
(b)
170
N
B
6.0
160
Cy
Cy
150
5.5
140
3.5
130
3.4
3.3
f1 (ppm)
5.0
4.5
120
4.0
f1 (ppm)
50
110
Me
S21
48
3.2
3.5
46
100
3.0
44
2.5
42
90
80
f1 (ppm)
2.0
40
70
1.5
38
36
f1 (ppm)
60
1.0
34
50
0.5
32
40
30
28
30
23.492
23.418
7.0
3.6
30.575
30.283
29.606
29.594
29.338
28.629
23.492
23.418
7.5
Pr
14.35
7.12
2.90
6.77
N
3.19
11.54
2.33
i
1.18
1.10
1.10
B
45.222
44.219
8.0
C
30.575
30.283
29.606
29.594
29.338
28.629
45.222
44.219
N
121.656
H
N
3.304
3.283
3.209
3.196
3.183
3.170
3.157
3.144
3.538
3.525
3.513
3.504
3.500
3.492
3.487
3.479
3.466
3.453
Me
130.698
129.708
Pr
141.171
i
153.588
2.35
2.00
(a)
Cy
Cy
3.1
0.0
26
20
24
10
0
1.368
1.343
1.113
1.099
0.730
0.717
2.100
2.008
1.919
1.914
1.764
1.762
3.538
3.525
3.513
3.504
3.500
3.492
3.487
3.479
3.466
3.453
3.304
3.283
3.209
3.196
3.183
3.170
3.157
3.144
7.105
7.101
7.097
7.088
7.084
7.080
6.985
6.984
6.968
6.966
12.008
(c)
Me
i
N
Pr
H
N
C
B
N
i
80
70
60
Cy
Cy
Pr
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
Figure S11. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 7.
S22
-60
-70
i
Pr
H
N
7.30
8.0
7.5
180
t
C
N
i
Pr
7.26
7.0
(b)
170
N
B
7.22
f1 (ppm)
6.5
160
Cy
Cy
150
7.18
6.0
5.5
140
130
120
45.283
44.273
31.660
30.610
30.280
29.594
29.573
29.248
28.640
23.519
23.470
7.14
3.6
3.5
5.0
4.5
f1 (ppm)
4.0
31
110
Bu
S23
100
3.4
29
3.3
f1 (ppm)
3.5
3.0
27
f1 (ppm)
90
80
f1 (ppm)
3.2
2.5
25
70
60
11.57
10.04
6.91
2.49
6.49
i
11.15
N
1.18
1.09
1.09
B
23.519
23.470
31.660
30.610
30.280
29.594
29.573
29.248
28.640
8.5
C
121.119
H
N
125.917
N
3.516
3.507
3.503
3.495
3.490
3.482
3.469
3.318
3.297
3.219
3.206
3.193
3.180
3.167
7.165
7.160
7.156
7.146
7.142
7.271
7.265
7.261
7.256
7.252
7.248
7.242
t
143.924
140.965
Pr
153.559
2.00
2.85
i
2.0
50
1.422
1.399
1.376
1.352
1.221
1.110
1.097
0.706
0.694
2.042
1.962
1.931
1.912
1.908
1.897
3.529
3.516
3.507
3.503
3.495
3.490
3.482
3.478
3.469
3.456
3.318
3.297
3.219
3.206
3.193
3.180
3.167
7.271
7.265
7.261
7.256
7.252
7.248
7.242
7.165
7.160
7.156
7.146
7.142
(a)
Bu
Cy
Cy
Pr
3.1
1.5
1.0
40
0.5
23
30
20
10
0
11.960
t
i
Pr
Bu
N
N
C
H
65
Cy
N
i
70
Cy
B
60
55
50
Pr
45
40
35
30
25
20
15
10
5
0
-5
f1 (ppm)
-10
-20
-30
-40
-50
Figure S12. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 8.
S24
-60
i
Pr
N
190
180
t
C
Cy2B
N
i
Pr
170
N
B
160
Cy
Cy
150
140
130
34
120
Bu
S25
1.8
4.0
3.5
f1 (ppm)
33
110
1.7 1.6
f1 (ppm)
32
1.5
3.0
100
90
f1 (ppm)
1.4
31
1.3
2.5
30
80
1.2
1.1
2.0
29
70
28
f1 (ppm)
60
N
1.5
C
N
1.0
27
50
B
Cy2B
N
i
0.5
26
40
25
30
24
20
23.117
22.821
1.9
7.81
9.83
1.99
3.69
2.137
2.042
1.956
1.930
1.828
1.803
1.782
1.595
1.573
1.459
1.432
1.405
1.374
1.347
1.321
1.241
1.228
1.218
1.205
1.169
1.149
1.121
1.107
3.675
3.662
3.649
3.636
3.623
3.950
t
24.197
4.5
2.0
46.71
2.1
Pr
34.281
31.562
29.669
29.608
28.913
28.650
28.635
28.413
27.491
27.407
24.762
24.197
5.0
2.2
1.00
0.91
i
44.670
5.5
2.3
53.346
6.0
3.5
120.093
6.5
3.6
125.807
7.0
3.9
3.8
3.7
f1 (ppm)
139.641
7.5
4.0
144.790
4.1
32.186
31.562
31.101
31.046
30.799
30.707
30.238
30.031
29.768
29.669
29.608
29.351
29.151
28.913
28.811
28.650
28.635
28.568
28.451
28.413
28.165
28.099
27.491
27.435
27.407
24.762
34.281
(b)
155.177
3.91
3.950
3.675
3.662
3.649
3.636
3.623
2.198
2.137
2.042
1.956
1.930
1.828
1.803
1.782
1.595
1.573
1.459
1.432
1.405
1.374
1.347
1.321
1.241
1.228
1.218
1.205
1.169
1.149
1.121
1.107
7.273
(a)
Bu
Cy
Cy
Pr
1.0
0.0
23
10
22
0
11.001
51.201
(c)
t
i
Pr
Bu
N
N
C
B
Cy2B
N
i
90
80
70
60
50
40
30
20
10
f1 (ppm)
0
-10
-20
-30
Cy
Pr
-40
Figure S13. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 9.
S26
Cy
-50
-60
(b)
41.075
39.919
39.709
39.322
39.306
37.243
36.993
36.356
36.051
34.428
34.244
33.954
29.781
29.723
6.5
160
6.0
43
42
150
5.5
41
140
5.0
40
39
130
1.5
4.5
38
120
1.3
4.0
3.5
f1 (ppm)
37
110
100
S27
3.0
36
35
f1 (ppm)
34
90
2.5
33
80
f1 (ppm)
32
70
10.88
6.38
2.12
1.9
1.7
f1 (ppm)
29.781
29.723
6.00
1.83
1.92
7.0
2.1
34.428
34.244
33.954
7.5
2.3
37.243
36.993
36.356
36.051
2.5
39.919
39.709
39.322
39.306
2.7
41.075
2.585
2.580
2.273
2.269
1.609
1.602
1.600
1.597
1.594
1.593
1.589
1.584
1.581
1.579
1.576
1.574
1.570
1.568
1.551
1.549
1.545
1.543
1.533
1.511
1.507
1.468
1.463
1.444
1.440
1.302
1.297
1.260
1.256
31
1.602
1.600
1.597
1.584
1.581
1.579
1.576
1.574
1.444
1.440
1.302
1.297
1.260
1.256
2.585
2.580
2.375
2.371
2.356
2.352
2.273
2.269
2.266
(a)
N
B
2.0
30
60
Nrb
Nrb
1.1
1.5
1.0
N
50
0.5
B
40
30
0.0
Nrb
Nrb
29
20
10
0
44.633
(c)
N
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
-40
-50
B
-60
Nrb
Nrb
-70
-80
-90
Figure S14. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 10 (diastereomer
mixture).
S28
2.590
1.824
1.810
1.803
1.623
1.591
1.480
1.475
1.450
1.445
1.341
1.328
1.322
1.292
1.824
1.810
1.803
1.623
1.591
1.480
1.475
1.450
1.445
1.341
1.328
1.322
1.292
N
2.3
2.1
1.9
f1 (ppm)
1.7
1.5
1.3
1.1
6.5
6.0
5.5
5.0
4.5
4.0
f1 (ppm)
3.5
(b)
N
43
170
42
160
40
150
2.5
2.0
1.5
1.0
0.5
40
30
0.0
Cy
B
41
3.0
28.892
28.774
27.733
7.0
30.923
7.5
40.132
8.0
30.923
28.892
28.774
27.733
2.5
Cy
30.41
2.7
6.00
2.9
Cy
B
40.132
2.590
(a)
Cy
39
140
38
37
130
36
35 34 33
f1 (ppm)
120
110
S29
32
100
31
30
29
90
80
f1 (ppm)
28
27
70
26
25
60
50
20
10
0
44.170
(c)
N
100
90
80
70
60
50
40
30
20
10
0
f1 (ppm)
-10
-20
-30
B
-40
Cy
Cy
-50
-60
-70
Figure S15. 1H (a), 13C{1H} (b) and 11B (c) NMR spectra for compound 11.
S30
-80
-90
-100