Appendix 1
Spectra Relevant to Chapter 2:
Synthesis and Utility of Chiral Allylic Silanes Prepared
via Ni-Catalyzed Asymmetric Reductive Cross-Coupling
Appendix 1 – Spectra Relevant to Chapter 2 205
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.45
B (qd) 7.22 C (d) 5.52
D (ddd) 5.32 E (dd) 3.38
F (dd) 3.19 G (m) 1.30 4.13
2.0 5
2.0 5
2.0 0
1.9 8
5.9 7
1.9 5
Value JLH-5-052.1.fid Bruker BioSpin GmbH CDCl3 295.0 zg30 16 112.8 1.0000 11.7000 4.0894 2016-08-19T15:53:20 ency400.13 8012.8 -1545.6 1H 32768 65536
L2
O NN
O
3040506070809010011012013014015016017018090 f1 (ppm) 39
.8
76 .5
83 .5
12 5.3
12 5.7
12 7.5
12 8.5
13 9.8
14 1.9
16 5.9
Value JLH-5-052.2.fid Bruker BioSpin GmbH CDCl3 295.0 zgpg30 128 87.8 2.0000 10.0000 1.3631 2016-08-19T16:01:10 ency100.62 24038.5 -1937.2 13C 32768 65536
L2
O NN
O
Appendix 1 – Spectra Relevant to Chapter 2 207
-505101520253035404550556065707580859095100105110 f1 (ppm)
A (s) 94.87B (s) 47.79C (s) 20.23D (s) 11.77
E (s) 11.51 F (s) 10.45
H (s) 3.92 I (s) -1.10
2.0 0
2.0 5
2.0 1
2.0 4
2.1 5
4.0 3
2.0 3
1.6 6
1.5 5
Value JLH-4-184-NiCl2BOX Varian "cdcl3" 22.0 s2pul 32 36 0.1000 4.1500 1.0000 2016-11-27T21:37:25 ency399.82 73529.4 -12777.0 1H 73529 262144
L2·NiCl2
O NN
O Ni ClCl
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.33
B (m) 7.27 C (m) 7.23
D (s) 4.37 0.90
1.0 0
1.9 6
1.9 5
Value JLH-4-198-F2-CH Varian "cdcl3" 25.0 s2pul 8 20 1.0000 5.9000 3.0000 2016-04-22T15:32:47 ency499.66 8000.0 -1002.1 1H 24000 65536
87
Cl
SiMe3
Appendix 1 – Spectra Relevant to Chapter 2 209
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.4
53 .1
12 6.7
12 7.0
12 8.3
14 0.3
Value JLH-4-198-F2-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-04-22T15:33:35 ency125.65 31446.5 -1903.0 13C 32768 65536
87
Cl
SiMe3
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.33
B (m) 7.24 C (s) 4.56D (dtt) 2.04
E (dtt) 1.90 F
1.1 3
1.1 7
1.0 0
1.1 4
4.1 8
Value JLH-2-177-Kugelrohr-CH Varian "cdcl3" 25.0 s2pul 32 24 1.0000 5.9000 3.0000 2016-04-22T00:08:32 ency499.66 8000.0 -1002.1 1H 24000 65536
89a
Cl
SiMe
Appendix 1 – Spectra Relevant to Chapter 2 211
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.4
13 .5
13 .8
17 .6
51 .7
12 6.9
12 6.9
12 8.5
13 9.5
Value JLH-2-177-Kugelrohr-CH Varian "cdcl3" 25.0 s2pul 1000 30 1.0000 4.5000 1.0420 2016-04-22T00:10:56 ency125.65 31446.5 -1903.0 13C 32768 65536
89a
Cl
SiMe
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.42
B (m) 7.35 C (m) 7.24
F (s) 4.51 0.99
2.0 7
1.0 7
2.2 8
2.1 3
3.2 5
Value JLH-6-202-distill-CH Varian cdcl3 25.0 s2pul 8 28 1.0000 5.8000 3.0000 2017-09-19T00:26:46 ency499.64 8000.0 -1002.2 1H 24000 65536
89b
Cl
SiMe2Ph
Appendix 1 – Spectra Relevant to Chapter 2 213
010203040506070809010011012013014015016017018090 f1 (ppm) -5
.1 -5 .1
52 .4
12 6.8
12 7.3
12 7.8
12 8.1
12 9.8
13 4.5
13 5.1
13 9.7
Value JLH-6-202-distill-CH Varian cdcl3 25.0 s2pul 256 30 1.0000 4.6125 1.0420 2017-09-19T00:27:35 ency125.65 31446.5 -1903.6 13C 32768 65536
89b
Cl
SiMe2Ph
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.30
B (m) 7.21 C (s) 4.48 1.00
1.0 1
4.0 6
Value JLH-2-031-CH Varian "cdcl3" 25.0 s2pul 8 20 1.0000 5.9000 3.0000 2016-04-22T15:18:57 ency499.66 8000.0 -1002.1 1H 24000 65536
89c
Cl
SiEt3
Appendix 1 – Spectra Relevant to Chapter 2 215
010203040506070809010011012013014015016017018090 f1 (ppm) 2.1
7.4
50 .9
12 6.7
12 7.2
12 8.4
14 0.7
Value JLH-2-031-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-04-22T15:19:45 ency125.65 31446.5 -1903.0 13C 32768 65536
89c
Cl
SiEt3
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (d) 7.58
B (d) 7.37 C (s) 4.39 1.00
2.0 6
2.0 6
Value JLH-4-255-distill-CH Varian "cdcl3" 25.0 s2pul 8 16 1.0000 5.9000 3.0000 2016-05-13T20:01:56 ency499.66 8000.0 -1002.1 1H 24000 65536
89d
Cl
SiMe3 F3C
Appendix 1 – Spectra Relevant to Chapter 2 217
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.6
52 .3
12 1.1
12 3.2
12 5.3
12 5.3
12 5.3
12 5.3
12 5.4
12 7.1
12 7.6
12 8.4
12 8.7
12 9.0
12 9.2
14 4.6
14 4.6
14 4.7
14 4.7
Value JLH-4-255-distill-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-05-13T20:02:44 ency125.65 31446.5 -1903.0 13C 32768 65536
89d
Cl
SiMe3 F3C
-160-150-140-130-120-110-100-90-80-70-60-50-40-30-200 f1 (ppm)
-6 5.6
Value JLH-4-255-F-CH Varian "cdcl3" 25.0 s2pul 16 30 1.0000 6.3333 0.9856 2016-10-11T14:22:53 ency282.34 64935.1 -56468.7 19F 64000 131072
89d
Cl
SiMe3 Cl
Appendix 1 – Spectra Relevant to Chapter 2 219
with C6F6 -190-180-170-160-150-140-130-120-110-100-90-80-70-60-50-40-30-200 f1 (ppm)
-6 5.6
Value JLH-4-255-F-C6F6-CH Varian "cdcl3" 25.0 s2pul 16 30 1.0000 6.3333 0.9856 2016-10-11T14:27:04 ency282.34 64935.1 -56468.7 19F 64000 131072
89d
Cl
SiMe3 Cl
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
C (s) 4.30A (m) 7.28
B (m) 7.18
1.0 0
2.0 4
1.9 8
Value JLH-3-250-CH Varian "cdcl3" 25.0 s2pul 8 22 1.0000 5.9000 3.0000 2016-06-04T19:34:47 ency499.66 8000.0 -1002.1 1H 24000 65536
89e
Cl
SiMe3 Br
Appendix 1 – Spectra Relevant to Chapter 2 221
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.5
52 .3
12 8.3
12 8.5
13 2.3
13 9.0
Value JLH-3-250-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-06-04T19:35:35 ency125.65 31446.5 -1903.0 13C 32768 65536
89e
Cl
SiMe3 Br
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.42
B (m) 7.12 C (s) 4.28 1.00
2.0 8
2.0 2
Value JLH-5-027-F3-CH Varian "cdcl3" 25.0 s2pul 32 34 1.0000 5.9000 3.0000 2016-06-03T23:09:22 ency499.66 8000.0 -1002.1 1H 24000 65536
89f
Cl
SiMe3 MeO
Appendix 1 – Spectra Relevant to Chapter 2 223
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.5
52 .3
12 0.3 12
8.6 13 1.4
13 9.5
Value JLH-5-027-F3-CH Varian "cdcl3" 25.0 s2pul 1000 30 1.0000 4.5000 1.0420 2016-06-03T23:11:46 ency125.65 31446.5 -1903.0 13C 32768 65536
89f
Cl
SiMe3 MeO
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (m) 7.22
B (ddq) 6.82 C (ddd) 6.76
D (s) 4.32E (s) 3.81 3.23
0.9 8
0.9 8
1.9 9
1.0 0
Value JLH-4-214-distill-CH Varian "cdcl3" 25.0 s2pul 8 22 1.0000 5.9000 3.0000 2016-04-22T00:50:02 ency499.66 8000.0 -1002.1 1H 24000 65536
89g
Cl
SiMe3 MeO
Appendix 1 – Spectra Relevant to Chapter 2 225
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.3
53 .0
55 .3
11 2.1
11 2.8
11 9.5
12 9.2
14 1.9
15 9.6
Value JLH-4-214-distill-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-04-22T00:50:50 ency125.65 31446.5 -1903.0 13C 32768 65536
89g
Cl
SiMe3 MeO
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dd) 7.41
B (ddd) 7.18 C (m) 6.98
E (s) 4.98F (s) 3.81 3.28
0.9 6
1.0 4
1.0 4
1.0 1
1.0 0
Value JLH-3-251-CH Varian "cdcl3" 25.0 s2pul 8 22 1.0000 5.9000 3.0000 2016-06-04T19:49:16 ency499.66 8000.0 -1002.1 1H 24000 65536
89i
Cl
SiMe3 OMe
Appendix 1 – Spectra Relevant to Chapter 2 227
010203040506070809010011012013014015016017018090 f1 (ppm) -3
.3
46 .1
55 .3
11 0.0
12 0.7
12 7.4
12 8.8
12 9.0
15 5.5
Value JLH-3-251-CH Varian "cdcl3" 25.0 s2pul 256 30 1.0000 4.5000 1.0420 2016-06-04T19:50:05 ency125.65 31446.5 -1903.0 13C 32768 65536
89i
Cl
SiMe3 OMe
1.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dt) 6.18
B (dt) 6.03 C (t) 3.61D (qd) 2.12
E (m) 1.61 2.00
1.9 1
2.1 5
0.8 9
0.9 0
Value JLH-3-232-CH Varian "cdcl3" 25.0 s2pul 8 24 1.0000 5.9000 3.0000 2016-10-08T17:53:05 ency499.66 8000.0 -1002.1 1H 24000 65536
S3
TBSOBr
