-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S107
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4a
abundance
01.02.03.04.05.06.07.08.09.010.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.7499
8.0794 7.5877 7.5751 7.4261 7.4135 7.4009 7.3573 7.3459 7.3344 7.2576
1.6734
0.0000
2.182.09
1.03
1.01
1
N
S
4a
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S108
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4a
abundance
00.10.20.30.40.50.60.70.80.91.01.11.21.3
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
152.0425
139.3646 139.0292
131.1138 129.1110
128.4402 127.0028
77.2108 77.0000 76.7892
N
S
4a
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S109
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4b
abundance010.020.030.040.050.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.6972
8.0267 7.4586 7.4444 7.2507 7.2014 7.1888
2.3623
-0.0000
3.13
2.031.91
1.00
0.98
N
SMe
4b
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S110
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4b
abundance01.02.03.04.0 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
151.4963
139.3741 138.5021 138.3679 129.6955 128.1814 126.7919
77.2108 77.0000 76.7892
21.1134
N
SMe
4b
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S111
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4c
abundance02.04.06.08.010.012.014.016.018.020.022.024.026.0 X
: pa
rts p
er M
illio
n : 1
H
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.7035
8.0410
7.5098 7.4960 7.4284 7.4141
1.33479.01
2.18 2.17
1.00
0.97
N
St-Bu
4c
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S112
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4c
abundance01.02.03.04.05.0 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
151.6305 151.5730
139.2687 138.5883
128.1815 126.6770 125.9678
77.2108 77.0000 76.7892
34.5963 31.1370
N
St-Bu
4c
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S113
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4e
abundance
010.020.030.040.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.7121
8.0450
7.1888
6.9768
2.34736.38
2.02
1.0
1
0.97
N
S
Me
Me 4e
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S114
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4e
abundance
01.02.03.0
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
151.6976
139.5754 138.7609 138.6842
130.8263 130.1076
124.7988
77.2109 77.0000 76.7796
21.1805
N
S
Me
Me 4e
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S115
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4f
abundance01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.017.018.019.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.8102 7.8428 7.3637 7.3511 7.2869 7.2846 7.2777 7.2410 7.2353 7.2284 7.2215
2.38013.02
2.98
1.02
1.00
1.00
N
S
Me
4f
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S116
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4f
abundance00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.9 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
152.5983
141.5973 137.3426 136.4035 130.7305 130.6730 130.2130 128.5839 126.0062
77.2108 77.0000 76.7892
20.9217
N
S
Me
4f
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S117
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4g
abundance010.020.030.040.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.6955
7.9751 7.5126 7.5092 7.5012 7.4977 7.2622 6.9499 6.9464 6.9390 6.9355
3.8449
-0.0000
2.98
2.12
2.10
1.00
0.95
N
SMeO
4g
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S118
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4g
abundance
00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.7
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
159.8045
151.1705
139.1633 138.0421
128.2294
123.6488
114.4781
77.2108 77.0000 76.7892
55.3238
N
SMeO
4g
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S119
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4h
abundance010.020.030.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.6858
7.9465
7.2702 7.0547 7.0525 7.0387 6.8393 6.8267 5.9980
0.0000
2.02
1.99
1.04
1.03
1.00
N
S
O
O
4h
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S120
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4h
abundance
0.100.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.6
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
151.3238 148.1999 147.8453
139.1633 138.3392
125.0000
120.9178
108.7764 107.3007
101.3690
77.2108 77.0000 76.7892
N
S
O
O
4h
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S121
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4i
abundance010.020.030.040.050.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.7373
8.0084
6.7659
3.9176 3.8833
0.0000
6.02 3.03
2.12
1.10
1.00
N
SMeO
MeO
MeO4i
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S122
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4i
abundance
01.02.03.0
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
153.5374 151.7167
139.3454 138.7417 138.4350
126.5428
104.4354
77.2108 77.0000 76.7892
60.8339
56.1479
N
SMeO
MeO
MeO4i
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S123
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4j
abundance
01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.017.018.019.020.021.022.023.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.7569
8.0497
7.5006 7.4857 7.4823 7.3803 7.3769 7.3665 7.3620
0.0000
2.222.22
1.04
1.03
N
SCl
4j
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S124
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4j
abundance
01.02.03.0
X :
part
s per
Mill
ion
: 13C
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
152.2821
139.2783 138.0804
134.2857
129.5614 129.2547 128.0856
77.2108 77.0000 76.7892
N
SCl
4j
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S125
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4k
abundance
01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.017.018.019.020.021.022.023.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.8221
8.1551
7.6931 7.6794 7.6714 7.6565
7.2691
0.0000
4.42
1.14
1
N
SF3C
4k
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S126
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4k
abundance
00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.3
X :
part
s per
Mill
ion
: 13C
190.
018
0.0
170.
016
0.0
150.
014
0.0
130.
012
0.0
110.
010
0.0
90.0
80.0
70.0
60.0
50.0
40.0
30.0
20.0
10.0
0
153.1062
140.1599 137.7355 134.5732 130.6059 130.3855 130.1747 129.9543 127.0890 126.1020 126.0733 124.7604 122.9493
77.2108 77.0000 76.7892
N
SF3C
4k
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S127
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4m
abundance01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.017.018.019.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.7763
8.0599 7.6066 7.6020 7.5986 7.5906 7.5877 7.5826 7.2731 7.2679 7.2588
-0.0000
2.10
2.03
1.01
1.00
N
SF3CO
4m
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S128
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4m
abundance00.10.20.30.40.50.6 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
152.5217 152.4642 149.1389 139.5083 139.4508 137.8121 129.8680 129.8297 128.3635 128.3060 122.9685 121.5789 121.5215 121.2531 119.5474 117.8417
77.2108 77.0000 76.7892
17.6157
-0.0645
N
SF3CO
4m
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S129
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4n
abundance
010.020.030.040.050.060.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.8153
8.1735 8.0772 8.0669 8.0634
7.6485 7.6451 7.6347
3.9372
0.0000
3.5
2.34
2.251.06
1
N
SMeO2C
4n
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S130
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4n
abundance
00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.8
X :
part
s per
Mill
ion
: 13C
190.
018
0.0
170.
016
0.0
150.
014
0.0
130.
012
0.0
110.
010
0.0
90.0
80.0
70.0
60.0
50.0
40.0
30.0
20.0
10.0
0
166.3400
153.0391
140.1216 138.1667 135.3589
130.3472 129.7722 126.6195
77.2108 77.0000 76.7892
52.1615
N
SMeO2C
4n
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S131
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4o
abundance
010.020.030.040.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.8270
8.1852 8.0052 7.9903
7.6785 7.6648
2.62503.21
2.36
2.1
1.01
1
N
SMeOC
4o
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S132
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4o
abundance01.02.0 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
197.0048
153.1445
140.1887 138.0517 136.5280 135.4739 129.1206 126.7920
77.2108 77.0000 76.7796
26.5085
N
SMeOC
4o
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S133
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4p
abundance010.020.030.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.8749
8.2181 8.0038 7.9900 7.7883 7.7745 7.2909
3.1027
0.0000
3.00
1.961.94
0.94
0.80
N
SMeO2S
4p
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S134
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4p
abundance00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.9 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
153.7482
140.7732 139.8820 137.1509 136.4322 128.2677 127.4532
77.2108 77.0000 76.7892
44.4378
N
SMeO2S
4p
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S135
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4q
abundance01.02.03.04.05.06.07.08.09.010.011.012.013.014.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.8932
8.2961 8.2812 8.2399 7.7596 7.7459 7.2771
-0.0000
2.00
1.92 0.96
0.94
N
SO2N
4q
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S136
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4q
abundance
0.100.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.5
X :
part
s per
Mill
ion
: 13C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
10.0
20.0
154.0932
147.3182
141.1278 137.4192 136.9113
127.3286 124.5017
77.2108 77.0000 76.7892
N
SO2N
4q
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S137
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4s
abundance01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.017.018.019.020.021.022.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.6479
7.8903
7.2611 7.0181 7.0123 6.7304 6.7246
2.8677 2.8551 2.8425 2.8299
1.3410 1.3284 1.3158
-0.0000
3.16
2.01
1.00
0.890.78
0.76
N
SS
Et4s
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S138
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4s
abundance00.10.20.30.40.50.60.70.80.91.01.11.21.31.4 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
150.9213 148.4202
138.6267
132.9920 130.0597 125.7283 124.2334
77.2108 77.0000 76.7892
23.4516
15.7854
-0.0357
N
SS
Et4s
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S139
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4t
abundance
01.02.03.04.05.06.07.08.09.010.011.012.013.014.015.016.0
X :
part
s per
Mill
ion
: 1H
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0
8.8772 8.6571 8.6549 8.6468
8.2674
7.4743 7.4720 7.4640 7.2932 7.2909
0.0000
2.19
2.17
1
0.98
N
SN
4t
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S140
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4t
abundance00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.6 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
153.0008 149.3977 147.7015
139.9395 135.4356 133.9503
127.2519 123.6872
77.2204 77.0000 76.7892
N
SN
4t
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S141
N
S1
2
34
5
1H NMR (600 MHz, CDCl3) of 4u
abundance01.02.03.04.05.06.07.08.09.010.0 X
: pa
rts p
er M
illio
n : 1
H
12.0
11.0
10.0
9.0
8.0
7.0
6.0
5.0
4.0
3.0
2.0
1.0
0-1
.0-2
.0
8.8772 8.6571 8.6549 8.6468 8.2674 7.4743 7.4720 7.4640 7.2932 7.2909
2.3062
0.0000
2.19
2.17
1.00
0.98
N
SN
4u
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013
-
Supporting Information (Tani, Uehara, Yamaguchi, Itami) Programmed Synthesis of Arylthiazoles through Sequential C–H Couplings
S142
N
S1
2
34
5
13C NMR (150 MHz, CDCl3) of 4u
abundance00.10.20.30.40.50.60.70.80.91.01.11.21.31.41.51.61.71.81.9 X
: pa
rts p
er M
illio
n : 1
3C
220.
021
0.0
200.
019
0.0
180.
017
0.0
160.
015
0.0
140.
013
0.0
120.
011
0.0
100.
090
.080
.070
.060
.050
.040
.030
.020
.010
.00
-10.
0-2
0.0
153.8345 150.5476
141.0128 138.3871 136.5089
120.8698
77.2108 77.0000 76.7796
N
SN
4u
Electronic Supplementary Material (ESI) for Chemical ScienceThis journal is © The Royal Society of Chemistry 2013