Appendix 3
Spectra Relevant to Chapter 3:
Decarboxylative Asymmetric Ni-Catalyzed Cross-Coupling of Benzylic
N-Hydroxyphthalimide Esters and Alkenyl Bromides
-50510152025303540455055606570758085909510010511015 f1 (ppm)
C (d) 20.16D (m) 11.34
E (d) 10.55 F (s) 6.96
G (s) 5.40 H (s) -0.65B (s) 46.46A (s) 96.48
2.0 0
2.0 2
1.9 3
2.0 7
6.1 0
2.0 0
1.7 2
1.6 0
ParameterValue leJLH-5-151-recryst ginVarian lventcdcl3 perature25.0 lse Sequences2pul mber of Scans64 eiver Gain30 axation Delay2.0000 lse Width4.1500 uisition Time1.9923 uisition Date2016-08-19T13:13:47 ectrometer Frequency399.81 ectral Width65789.5 west Frequency-13264.8 cleus1H uired Size131072 ectral Size262144
L2·NiBr2
O NN
O Ni BrBr
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (s) 3.02B (s) 2.29 19.76
1.0 0
Value JLH-5-150 Varian "cdcl3" 25.0 s2pul 8 0 1.0000 5.1000 2.4999 2016-08-18T01:32:15 ency300.09 4796.2 -597.5 1H 11990 65536
S29
NMe2 NMe2Me2N
010203040506070809010011012013014015016017018019020010 f1 (ppm)
41 .3
10 0.3
ParameterValue leJLH-5-150.2.fid ginBruker BioSpin GmbH lventCDCl3 perature294.9 lse Sequencezgpg30 mber of Scans128 eiver Gain72.0 axation Delay2.0000 lse Width10.0000 uisition Time1.3631 uisition Date2016-08-19T15:48:48 ectrometer Frequency100.62 ectral Width24038.5 west Frequency-1958.0 cleus13C uired Size32768 ectral Size65536
S29
NMe2 NMe2Me2N
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (s) 2.57 24.00
Value JLH-5-168-D2F3 Varian cdcl3 24.0 s2pul 1 20 1.0000 4.1500 20.4472 2016-08-30T22:06:00 ency399.80 6410.3 -808.0 1H 131072 262144
TDAE
NMe2 NMe2Me2N
Me2N
0102030405060708090100110120130140150160170180190200210 f1 (ppm)
41 .2
13 1.5
ParameterValue leJLH-5-168-D2F3-carbon ginVarian lventcdcl3 perature24.0 lse Sequences2pul mber of Scans36 eiver Gain30 axation Delay1.0000 lse Width3.5125 uisition Time1.3107 uisition Date2016-08-30T22:15:08 ectrometer Frequency100.54 ectral Width25000.0 west Frequency-1402.1 cleus13C uired Size32768 ectral Size65536
TDAE
NMe2 NMe2Me2N
Me2N
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dd) 7.85
B (dd) 7.76 C (m) 7.40
D (m) 7.33 E (q) 4.13F (d) 1.68 2.98
0.9 9
0.9 9
3.9 4
2.0 0
1.9 2
Value NAO-01-071-A.1.fid Bruker BioSpin GmbH CDCl3 294.9 zg30 16 55.5 1.0000 11.7000 4.0894 2016-08-17T23:57:55 ency400.13 8012.8 -1555.6 1H 32768 65536
136
Me O O
N
O O
010203040506070809010011012013014015016017018019020010 f1 (ppm)
19 .1
43 .1
12 4.0
12 7.7
12 7.9
12 9.0
12 9.0
13 4.9
13 8.5
16 1.9 17 0.9
ParameterValue leNAO-01-071-A.2.fid ginBruker BioSpin GmbH lventCDCl3 perature295.0 lse Sequencezgpg30 mber of Scans128 eiver Gain64.2 axation Delay2.0000 lse Width10.0000 uisition Time1.3631 uisition Date2016-08-18T00:05:45 ectrometer Frequency100.62 ectral Width24038.5 west Frequency-1942.9 cleus13C uired Size32768 ectral Size65536 127.5128.0128.5129.0 f1 (ppm)
136
Me O O
N
O O
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dd) 7.86
B (dd) 7.77 C (d) 7.33D (d) 6.92E (q) 4.08
F (s) 3.81 G (d) 1.65 3.06
2.8 8
1.0 0
1.9 8
1.9 8
2.0 1
1.8 7
Value NAO-01-174-A.1.fid Bruker BioSpin GmbH CDCl3 295.0 zg30 16 78.7 1.0000 11.7000 4.0894 2016-08-18T00:56:19 ency400.13 8012.8 -1555.6 1H 32768 65536
62a
Me O O
N
O OMeO
010203040506070809010011012013014015016017018019020010 f1 (ppm)
19 .2
42 .2
55 .4
11 4.4
12 4.0
12 8.8
12 9.0
13 0.5
13 4.9
15 9.2
16 2.0
17 1.1
ParameterValue leNAO-01-174-A.2.fid ginBruker BioSpin GmbH lventCDCl3 perature294.9 lse Sequencezgpg30 mber of Scans128 eiver Gain72.0 axation Delay2.0000 lse Width10.0000 uisition Time1.3631 uisition Date2016-08-18T01:04:09 ectrometer Frequency100.62 ectral Width24038.5 west Frequency-1938.0 cleus13C uired Size32768 ectral Size65536 128.5129.0129.5130.0130.5 f1 (ppm) 12
8.8 12 9.0
13 0.5
62a
Me O O
N
O OMeO
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
E (q) 4.19F (d) 1.69C (d) 7.66
D (d) 7.54 B (dd) 7.78
A (dd) 7.87
3.0 6
0.9 9
2.0 2
2.0 7
2.1 2
2.0 9
Value NAO-01-176-A.1.fid Bruker BioSpin GmbH CDCl3 295.0 zg30 16 98.9 1.0000 11.7000 4.0894 2016-08-17T22:00:38 ency400.13 8012.8 -1535.6 1H 32768 65536
62b
Me O O
N
O OF3C
010203040506070809010011012013014015016017018019020010 f1 (ppm)
19 .1
43 .0
12 0.1
12 2.8
12 4.1
12 5.5
12 6.0
12 6.0
12 6.1
12 6.1
12 8.2
12 8.9
12 9.8
13 0.1
13 0.4
13 0.7
13 5.0
14 2.4
14 2.4
14 2.4
14 2.4
16 1.9 17 0.3
ParameterValue leNAO-01-176-A.2.fid ginBruker BioSpin GmbH lventCDCl3 perature294.9 lse Sequencezgpg30 mber of Scans128 eiver Gain64.2 axation Delay2.0000 lse Width10.0000 uisition Time1.3631 uisition Date2016-08-17T22:08:28 ectrometer Frequency100.62 ectral Width24038.5 west Frequency-1934.6 cleus13C uired Size32768 ectral Size65536 142.3142.5 f1 (ppm)142.4 14
2.4 14 2.4
14 2.4
120122124126128130132 f1 (ppm) 12
0.1
12 2.8
12 5.5
12 6.0
12 6.0
12 6.1
12 6.1
12 8.9
12 9.8
13 0.1
13 0.4
13 0.7
62b
Me O O
N
O OF3C
-190-180-170-160-150-140-130-120-110-100-90-80-70-60-50-40-30-20-10 f1 (ppm)
-6 5.8
Value NAO-01-176A Varian "cdcl3" 25.0 s2pul 16 30 1.0000 6.3333 0.9856 2016-08-31T23:19:24 ency282.34 64935.1 -58259.3 19F 64000 131072
62b
Me O O
N
O OF3C
-190-180-170-160-150-140-130-120-110-100-90-80-70-60-50-40-30-20-100100 f1 (ppm)
-6 5.8
ParameterValue leNAO-01-176A-C6F6 ginVarian lvent"cdcl3" perature25.0 lse Sequences2pul mber of Scans16 eiver Gain30 axation Delay1.0000 lse Width6.3333 uisition Time0.9856 uisition Date2016-08-31T23:23:38 ectrometer Frequency282.34 ectral Width64935.1 west Frequency-58249.7 cleus19F uired Size64000 ectral Size131072
with C6F662b
Me O O
N
O OF3C
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dd) 7.86
B (m) 7.78 C (d) 7.52D (d) 7.29E (q) 4.08F (d) 1.65 3.10
1.0 0
2.0 0
2.0 1
2.1 1
2.0 2
Value NAO-01-199-A.2.fid Bruker BioSpin GmbH CDCl3 294.9 zg30 16 112.8 1.0000 11.7000 4.0894 2016-08-19T23:03:07 ency400.13 8012.8 -1555.6 1H 32768 65536
62c
Me O O
N
O OBr
010203040506070809010011012013014015016017018019020010 f1 (ppm)
19 .0
42 .6
12 2.0
12 4.1
12 9.0
12 9.4
13 2.2
13 4.9
13 7.4
16 1.9 17 0.5
ParameterValue leNAO-01-199-A.3.fid ginBruker BioSpin GmbH lventCDCl3 perature294.9 lse Sequencezgpg30 mber of Scans128 eiver Gain72.0 axation Delay2.0000 lse Width10.0000 uisition Time1.3631 uisition Date2016-08-19T23:11:04 ectrometer Frequency100.62 ectral Width24038.5 west Frequency-1937.5 cleus13C uired Size32768 ectral Size65536
62c
Me O O
N
O OBr
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0.5 f1 (ppm)
A (dd) 7.86
B (dd) 7.77 C (m) 7.38D (m) 7.08E (q) 4.11F (d) 1.66 3.05
1.0 0
1.9 8
1.9 8
1.9 9
1.9 2
Value NAO-01-194-A.1.fid Bruker BioSpin GmbH CDCl3 294.9 zg30 16 87.8 1.0000 11.7000 4.0894 2016-09-23T19:21:20 ency400.13 8012.8 -1535.6 1H 32768 65536
62d
Me O O
N
O OF
