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