(IPr)CuF-Catalyzed α-Site Regiocontrolled trans ... · PDF file S1 (IPr)CuF-Catalyzed...

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  • S1

    (IPr)CuF-Catalyzed α-Site Regiocontrolled trans-Hydrofluorination

    of Ynamides

    Guohao Zhu, Shineng Qiu, Yang Xi, Yao Ding, Dongming Zhang, Rong Zhang,

    Guangke He∗ and

    Hongjun Zhu∗

    Department of Applied Chemistry, College of Chemistry and Molecular Engineering, Nanjing

    Tech University, Nanjing 211816, People’ s Republic of China

    *E-mails: hegk@njtech.edu.cn; zhuhj@njtech.edu.cn.

    Spectra of compounds Z-2a-4o

    Spectra of compound Z-2a p 2-4 Spectra of compound Z-2k p 33-35

    Spectra of compound Z-3a p 5 Spectra of compound Z-3k p 36

    Spectra of compound Z-2b p 6-8 Spectra of compound Z-2l p 37-39

    Spectra of compound Z-2c p 9-11 Spectra of compound Z-3l p 40

    Spectra of compound Z-2d p 12-14 Spectra of compound Z-2m p 41-43

    Spectra of compound Z-2e p 15-17 Spectra of compound Z-2n p 44-46

    Spectra of compound Z-2f p 18-20 Spectra of compound Z-2o p 47-49

    Spectra of compound Z-2g p 21-23 Spectra of compound Z-2p p 50-52

    Spectra of compound Z-2h p 24-26 Spectra of compound 4a p 53-55

    Spectra of compound Z-2i p 27-29 Spectra of compound 4o p 56-58

    Spectra of compound Z-2j p 30-32 Detailed discussions p 59-60

    Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2016

    mailto:hegk@njtech.edu.cn mailto:zhuhj@njtech.edu.cn

  • 10 9

    8 7

    6 5

    4 3

    2 1

    0 pp

    m

    −0.0000

    1.6214

    3.9506 3.9539 3.9733 3.9905 3.9938 4.4338 4.4508 4.4545 4.4737

    5.9154 6.0027

    7.2134 7.2318 7.2502 7.2589 7.3120 7.3316 7.3502 7.4454 7.4641

    2.10

    2.09

    1.00

    1.36 2.10 2.10

    z g h − 2 − 1 7 6 − H

  • 17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 0

    pp m

    44.0761

    62.0310

    76.7284 77.0459 77.3637

    99.2639 99.3998

    127.1742 127.1974 128.3079 128.3810 128.5405 132.1570 132.2110 144.4725 147.1063

    154.1797

    z g h − 2 − 1 7 6 − C

  • −3 0

    −4 0

    −5 0

    −6 0

    −7 0

    −8 0

    −9 0

    −1 00

    −1 10

    −1 20

    −1 30

    −1 40

    −1 50

    pp m

    −99.2869

    z g h − 2 − 1 7 6 − F

  • 10 9

    8 7

    6 5

    4 3

    2 1

    0 pp

    m

    0.0000

    1.6044

    4.1806 4.1898 4.1997 4.2038 4.2089 4.2208 4.2300 4.4576 4.4786 4.4978

    6.6948 6.7724 7.2621 7.3063 7.3209 7.3242 7.3275 7.3478 7.3678 7.3859 7.4427 7.4610 7.4648

    2.06

    2.06

    1.00

    1.01 2.03 2.03

    z g h − 6 − 4 1 ( 2 ) − H

  • 10 9

    8 7

    6 5

    4 3

    2 1

    0 pp

    m

    −0.0000

    1.6363

    2.3356

    3.9359 3.9394 3.9588 3.9758 3.9793 4.4257 4.4428 4.4462 4.4657

    5.8625 5.9493

    7.1280 7.1480 7.2584 7.3383 7.3586

    3.29

    2.16

    2.18

    1.00

    2.09 2.19

    z g h − 2 − 1 5 8 − H

  • 17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 0

    pp m

    20.1695

    43.1707

    61.0706

    75.7839 76.1028 76.4204

    98.5790 98.7232

    127.1743 127.2470 128.2251 136.0400 136.0621 143.0354 145.6695

    153.3398

    z g h − 2 − 1 5 8 − C

  • −3 0

    −4 0

    −5 0

    −6 0

    −7 0

    −8 0

    −9 0

    −1 00

    −1 10

    −1 20

    −1 30

    −1 40

    −1 50

    pp m

    −99.8240

    z g h − 2 − 1 5 8 − F

  • 11 10

    9 8

    7 6

    5 4

    3 2

    1 0

    pp m

    −0.0000

    1.5836

    3.8146 3.9400 3.9470 3.9636 3.9667 3.9793 3.9862 4.4343 4.4429 4.4557 4.4588 4.4626 4.4646 4.4741 4.4827 5.8285 5.8335 5.9142 5.9193 6.8621 6.8839 7.2631 7.3917 7.4136

    3.22 2.10

    2.09

    1.00

    2.08

    2.07

    z g h − 2 − 1 7 8 − H

  • 21 0

    20 0

    19 0

    18 0

    17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 0

    pp m

    44.3281

    55.2408

    62.1106

    76.7795 77.0970 77.4152

    100.0712 100.2221

    113.9769

    124.6053 124.6629 129.6482 129.7229

    143.3047 145.9325

    154.5499 158.7374 158.7656

    z g h − 2 − 1 7 8 − C

  • −4 0

    −5 0

    −6 0

    −7 0

    −8 0

    −9 0

    −1 00

    −1 10

    −1 20

    −1 30

    −1 40

    −1 50

    pp m

    −101.1844

    z g h − 2 − 1 7 8 − F

  • 10 9

    8 7

    6 5

    4 3

    2 1

    0 pp

    m

    0.0000

    1.5827

    3.9648 3.9682 3.9847 3.9878 4.0047 4.0081 4.4496 4.4664 4.4700 4.4895

    5.9064 5.9935

    7.2623 7.2806 7.3021 7.3648 7.3862

    2.12

    2.14

    1.00

    2.00 2.13

    z g h − 6 − 6 3 − H

  • 19 0

    18 0

    17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 0

    pp m

    43.9588

    62.0486

    76.7393 77.0564 77.3746

    97.7155 97.8515

    128.7164 129.4867 129.5608 130.7747 130.8279 132.6984 132.7330 144.8934 147.5247 153.9960

    z g h − 6 − 6 3 − C

  • −1 80

    −1 60

    −1 40

    −1 20

    −1 00

    −8 0

    −6 0

    −4 0

    −2 0

    0 pp

    m

    −98.9613

    z g h − 6 − 6 3 − F

  • 11 10

    9 8

    7 6

    5 4

    3 2

    1 0

    pp m

    0.0000

    1.5828

    3.9658 3.9688 3.9863 3.9882 4.0056 4.0086 4.4499 4.4704 4.4898

    5.8960 5.9834

    7.2625 7.2989 7.3202 7.4351 7.4564

    2.11

    2.13

    1.00

    2.05 2.15

    z g h − 2 − 1 6 1 − H

  • 20 0

    19 0

    18 0

    17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 pp

    m

    43.9258

    62.0502

    76.7411 77.0585 77.3763

    97.6167 97.7486

    120.8242 120.8556 129.7788 129.8528 131.2374 131.2916 131.6737 144.9764 147.6081 153.9525

    z g h − 2 − 1 6 1 − C

  • −1 80

    −1 60

    −1 40

    −1 20

    −1 00

    −8 0

    −6 0

    −4 0

    −2 0

    0 pp

    m

    −98.6946

    z g h − 2 − 1 6 1 − F

  • 10 9

    8 7

    6 5

    4 3

    2 1

    0 pp

    m

    0.0000

    1.5768

    3.9615 3.9808 4.0013 4.4495 4.4707 4.4894

    5.8935 5.9797

    6.9997 7.0214 7.0431 7.2622 7.4071 7.4209 7.4288 7.4425

    2.10

    2.15

    1.00

    2.05

    2.20

    z g h − 6 − 6 4 − H

  • 19 0

    18 0

    17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 pp

    m

    44.0833

    62.0768

    76.7403 77.0588 77.3755

    98.4645 98.6074

    115.4007 115.6148 128.2607 128.2941 128.3466 129.9232 129.9993 130.0774 144.2729 146.9043

    154.2216 160.5061 160.5378 162.9642 162.9966

    z g h − 6 − 6 4 − C

  • −1 80

    −1 60

    −1 40

    −1 20

    −1 00

    −8 0

    −6 0

    −4 0

    −2 0

    0 pp

    m

    −114.1784

    −100.4135

    z g h − 6 − 6 4 − F

  • 11 10

    9 8

    7 6

    5 4

    3 2

    1 0

    pp m

    −0.0000

    1.7066

    2.5927

    4.0104 4.0301 4.0483 4.0503 4.4699 4.4906 4.5098

    6.0377 6.1270

    7.2726 7.5052 7.5263 7.9013 7.9223

    3.01

    2.01

    2.03

    1.00

    2.02

    2.03 z g h − 2 − 1 8 0 − H

  • 20 0

    19 0

    18 0

    17 0

    16 0

    15 0

    14 0

    13 0

    12 0

    11 0

    10 0

    90 80

    70 60

    50 40

    30 20

    10 pp

    m

    26.5454

    43.7797

    62.0890

    76.8038 77.1220 77.4406

    96.4795 96.5977

    128.1245 128.2015 128.6266 135.1678 135.1877 137.4290 137.4839 146.1508 148.7939 153.6775

    197.5101

    z g h − 2 − 1 8 0 − C

  • −1 60

    −1 40

    −1 20

    −1 00

    −8 0

    −6 0

    −4 0

    −2 0

    0 pp

    m

    −96.7446

    z g h − 2 − 1 8 0 − F

  • 11 10

    9 8

    7 6

    5 4

    3 2

    1 0

    pp m

    −0.0000

    1.6125

    4.0464 4.0487 4.0661 4.0686 4.0861 4.0887 4.4961 4.5130 4.5166 4.5360

    6.1416 6.2316

    7.