Copper-Catalyzed Carbenoid Insertion Reactions of α-diazoesters and α-diazoketones into Si H and S H Bonds
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1 Supporting Information for: Copper-Catalyzed Carbenoid Insertion Reactions of α-diazoesters and α-diazoketones into Si H and S H Bonds Hoda Keipour, Angela Jalba, Léo Delage-Laurin, Thierry Ollevier * Département de chimie, Université Laval, 1045 avenue de la Médecine Québec, QC, G1V 0A6, Canada S-1
2 CONTENT 1 H and 13 C NMR of p-tosyl Azide... S-5 1 H and 13 C NMR of p-acetamidobenzenesulfonyl Azide... S-6 1 H and 13 C NMR of Methanesulfonyl Azide... S-7 1 H and 13 C NMR of Methyl α-diazophenylacetate (1a)... S-8 1 H and 13 C NMR of Methyl α-diazo-4-methylphenylacetate (1b)... S-9 1 H and 13 C NMR of Methyl α-diazo-2-methylphenylacetate (1c)... S-10 1 H and 13 C NMR of Methyl α-diazo-4-methoxylphenylacetate (1d)... S-11 1 H and 13 C NMR of Methyl α-diazo-4-fluorophenylacetate (1e)... S-12 1 H and 13 C NMR of Methyl α-diazo-3-fluorophenylacetate (1f)... S-13 1 H and 13 C NMR of Methyl α-diazo-4-chlorophenylacetate (1g)... S-14 1 H and 13 C NMR of Methyl α-diazo-3-chlorophenylacetate (1h)... S-15 1 H and 13 C NMR of Methyl α-diazo-2-chlorophenylacetate (1i)... S-16 1 H and 13 C NMR of Methyl α-diazo-4-bromophenylacetate (1j)... S-17 1 H and 13 C NMR of Methyl α-diazo-3-bromophenylacetate (1k)... S-18 1 H and 13 C NMR of Ethyl α-diazophenylacetate (1l)... S-19 1 H and 13 C NMR of Isobutyl α-diazophenylacetate (1m)... S-20 1 H and 13 C NMR of Allyl α-diazophenylacetate (1n)... S-21 1 H and 13 C NMR of Methyl α-phenyl-α-triethylsilylacetate (2a)... S-22 1 H and 13 C NMR of Methyl α-(4-methylphenyl)-α-triethylsilylacetate (2b)... S-23 1 H and 13 C NMR of Methyl α-(2-methylphenyl)-α-triethylsilylacetate (2c)... S-24 1 H and 13 C NMR of Methyl α-(4-methoylphenyl)-α-triethylsilylacetate (2d)... S-25 1 H and 13 C NMR of Methyl α-(4-fluorophenyl)-α-triethylsilylacetate (2e)... S-26 1 H and 13 C NMR of Methyl α-(3-fluorophenyl)-α-triethylsilylacetate (2f)... S-27 1 H and 13 C NMR of Methyl α-(4-chlorophenyl)-α-triethylsilylacetate (2g)... S-28 1 H and 13 C NMR of Methyl α-(3-chlorophenyl)-α-triethylsilylacetate (2h)... S-29 1 H and 13 C NMR of Methyl α-(2-chlorophenyl)-α-triethylsilylacetate (2i)... S-30 1 H and 13 C NMR of Methyl α-(4-bromophenyl)-α-triethylsilylacetate (2j)... S-31 1 H and 13 C NMR of Methyl α-(3-bromophenyl)-α-triethylsilylacetate (2k)... S-32 1 H and 13 C NMR of Ethyl α-phenyl-α-triethylsilylacetate (2l)... S-33 1 H and 13 C NMR of Isobutyl α-phenyl-α-triethylsilylacetate (2m)... S-34 1 H and 13 C NMR of Allyl α-phenyl-α-triethylsilylacetate (2n)... S-35 S-2
3 1 H and 13 C NMR of Methyl 2-(Benzylthio)-2-phenylacetate (3a)... S-36 1 H and 13 C NMR of Methyl 2-(Benzylthio)-2-(4-chlorophenyl)-acetate (3b)... S-37 1 H and 13 C NMR of Methyl 2-Phenyl-2-(phenylthio)acetate (3c)... S-38 1 H and 13 C NMR of Methyl 2-((4-Methoxyphenyl)thio)-2-phenylacetate (3d)... S-39 1 H and 13 C NMR of Methyl 2-((4-Chlorophenyl)thio)-2-phenylacetate (3e)... S-40 1 H and 13 C NMR of Methyl 2-Phenyl-2-(p-tolylthio)acetate (3f)... S-41 1 H and 13 C NMR of Methyl 2-(4-Methoxyphenyl)-2-(phenylthio)acetate (3g)... S-42 1 H and 13 C NMR of Methyl 2-(Phenylthio)-2-(p-tolyl)acetate (3h)... S-43 1 H and 13 C NMR of Methyl 2-(4-Chlorophenyl)-2-(phenylthio)acetate (3i)... S-44 1 H and 13 C NMR of Methyl 2-(4-Bromophenyl)-2-(phenylthio)acetate (3j)... S-45 1 H and 13 C NMR of Ethyl 2-Phenyl-2-(phenylthio)acetate (3k)... S H and 13 C NMR of Isobutyl 2-Phenyl-2-(phenylthio)acetate (3l)... S-47 1 H and 13 C NMR of Methyl 1,2-Diphenylcyclopropane-1-carboxylate (4)... S-48 1 H and 13 C NMR of Allyl 2-Phenylacetate (6)... S-49 1 H and 13 C NMR of 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (7)... S-50 1 H and 13 C NMR of 2-Diazo-1-phenylpropan-1-one (8a)... S-51 1 H and 13 C NMR of 2-Diazo-1-(p-tolyl)propan-1-one (8b)... S-52 1 H and 13 C NMR of 2-Diazo-1-(p-chlorophenyl)propan-1-one (8c)... S-53 1 H and 13 C NMR of 2-Diazo-1-(p-fluorophenyl)propan-1-one (8d)... S-54 1 H and 13 C NMR of 1-(Benzo[d][1,3]dioxol-5-yl)-2-diazopropan-1-one (8e)... S-55 1 H and 13 C NMR of 2-Diazo-1,2-diphenylethan-1-one (8f)... S-56 1 H and 13 C NMR of 1-Diazo-1-phenylpropan-2-one (8g)... S-57 1 H and 13 C NMR of 2-Diazo-1-phenylbutan-1-one (8h)... S-58 1 H and 13 C NMR of 1-Phenyl-2-(triethylsilyl)propan-1-one (9a)... S-59 1 H and 13 C NMR of 1-(p-Tolyl)-2-(triethylsilyl)propan-1-one (9b)... S-60 1 H and 13 C NMR of 1-(4-Chlorophenyl)-2-(triethylsilyl)propan-1-one (9c)... S-61 1 H and 13 C NMR of 1-(4-Fluorophenyl)-2-(triethylsilyl)propan-1-one (9d)... S-62 1 H and 13 C NMR of 1-(Benzo[d][1,3]dioxol-5-yl)-2-(triethylsilyl)propan-1-one (9e).. S H and 13 C NMR of 1,2-Diphenyl-2-(triethylsilyl)ethan-1-one (9f)... S-64 1 H and 13 C NMR of 1-Phenyl-1-(triethylsilyl)propan-2-one (9g)... S-65 1 H and 13 C NMR of 1-Phenyl-2-(triethylsilyl)butan-1-one (9h)... S-66 1 H NMR of (E)-1-Phenylbut-2-en-1-one (9h')... S-67 S-3
4 1 H and 13 C NMR of Methyl 2-Hydroxy-2-phenylacetate (10)...S-68 1 H and 13 C NMR of Methyl-2,3-diphenylacrylate (11)... S-69 1 H and 13 C NMR of 2-Phenyl-2-(triethylsilyl)ethan-1-ol (12)... S-70 1 H and 13 C NMR of 2-Phenyl-2-(triethylsilyl)ethyl 2-phenylacetate (13)... S-71 1 H and 13 C NMR of 2-Phenyl-2-(triethylsilyl)ethyl 2-diazo-2-phenylacetate (14)... S-72 1 H and 13 C NMR of (E)-(1,3-Diphenylallyl)triethylsilane (16)... S-73 S-4
5 p-tosyl Azide S-5
6 p-acetamidobenzenesulfonyl Azide S-6
7 Methanesulfonyl Azide S-7
8 Methyl α-diazophenylacetate (1a) S-8
9 Methyl α-diazo-4-methylphenylacetate (1b) S-9
10 Methyl α-diazo-2-methylphenylacetate (1c) S-10
11 Methyl α-diazo-4-methoxylphenylacetate (1d) S-11
12 Methyl α-diazo-4-fluorophenylacetate (1e) S-12
13 Methyl α-diazo-3-fluorophenylacetate (1f) S-13
14 Methyl α-diazo-4-chlorophenylacetate (1g) S-14
15 Methyl α-diazo-3-chlorophenylacetate (1h) S-15
16 Methyl α-diazo-2-chlorophenylacetate (1i) S-16
17 Methyl α-diazo-4-bromophenylacetate (1j) S-17
18 Methyl α-diazo-3-bromophenylacetate (1k) S-18
19 Ethyl α-diazophenylacetate (1l) S-19
20 Isobutyl α-diazophenylacetate (1m) S-20
21 Allyl α-diazophenylacetate (1n) S-21
22 Methyl α-phenyl-α-triethylsilylacetate (2a) S-22
23 Methyl α-(4-methylphenyl)-α-triethylsilylacetate (2b) S-23
24 Methyl α-(2-methylphenyl)-α-triethylsilylacetate (2c) S-24
25 Methyl α-(4-methoylphenyl)-α-triethylsilylacetate (2d) S-25
26 Methyl α-(4-fluorophenyl)-α-triethylsilylacetate (2e) S-26
27 Methyl α-(3-fluorophenyl)-α-triethylsilylacetate (2f) S-27
28 Methyl α-(4-chlorophenyl)-α-triethylsilylacetate (2g) S-28
29 Methyl α-(3-chlorophenyl)-α-triethylsilylacetate (2h) S-29
30 Methyl α-(2-chlorophenyl)-α-triethylsilylacetate (2i) S-30
31 Methyl α-(4-bromophenyl)-α-triethylsilylacetate (2j) S-31
32 Methyl α-(3-bromophenyl)-α-triethylsilylacetate (2k) S-32
33 SiEt 3 OEt Ethyl α-phenyl-α-triethylsilylacetate (2l) O S-33
34 Isobutyl α-phenyl-α-triethylsilylacetate (2m) S-34
35 Allyl α-phenyl-α-triethylsilylacetate (2n) S-35
36 Methyl 2-(Benzylthio)-2-phenylacetate (3a) S-36
37 Methyl 2-(Benzylthio)-2-(4-chlorophenyl)-acetate (3b) S-37
38 Methyl 2-Phenyl-2-(phenylthio)acetate (3c) S-38
39 Methyl 2-((4-Methoxyphenyl)thio)-2-phenylacetate (3d) S-39
40 Methyl 2-((4-Chlorophenyl)thio)-2-phenylacetate (3e) S-40
41 Methyl 2-Phenyl-2-(p-tolylthio)acetate (3f) S-41
42 Methyl 2-(4-Methoxyphenyl)-2-(phenylthio)acetate (3g) S-42
43 Methyl 2-(Phenylthio)-2-(p-tolyl)acetate (3h) S-43
44 Methyl 2-(4-Chlorophenyl)-2-(phenylthio)acetate (3i) S-44
45 Methyl 2-(4-Bromophenyl)-2-(phenylthio)acetate (3j) S-45
46 Ethyl 2-Phenyl-2-(phenylthio)acetate (3k) S-46
47 Isobutyl 2-Phenyl-2-(phenylthio)acetate (3l) S-47
48 Methyl 1,2-Diphenylcyclopropane-1-carboxylate (4) S-48
49 Allyl 2-Phenylacetate (6) S-49
50 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one (7) S-50
51 2-Diazo-1-phenylpropan-1-one (8a) S-51
52 2-Diazo-1-(p-tolyl)propan-1-one (8b) S-52
53 2-Diazo-1-(p-chlorophenyl)propan-1-one (8c) S-53
54 2-Diazo-1-(p-fluorophenyl)propan-1-one (8d) S-54
55 1-(Benzo[d][1,3]dioxol-5-yl)-2-diazopropan-1-one (8e) S-55
56 2-Diazo-1,2-diphenylethan-1-one (8f) S-56
57 1-Diazo-1-phenylpropan-2-one (8g) S-57
58 2-Diazo-1-phenylbutan-1-one (8h) S-58
59 1-Phenyl-2-(triethylsilyl)propan-1-one (9a) S-59
60 1-(p-Tolyl)-2-(triethylsilyl)propan-1-one (9b) S-60
61 1-(4-Chlorophenyl)-2-(triethylsilyl)propan-1-one (9c) S-61
62 1-(4-Fluorophenyl)-2-(triethylsilyl)propan-1-one (9d) S-62
63 1-(Benzo[d][1,3]dioxol-5-yl)-2-(triethylsilyl)propan-1-one (9e) S-63
64 1,2-Diphenyl-2-(triethylsilyl)ethan-1-one (9f) S-64
65 1-Phenyl-1-(triethylsilyl)propan-2-one (9g) S-65
66 1-Phenyl-2-(triethylsilyl)butan-1-one (9h) S-66
67 (E)-1-Phenylbut-2-en-1-one (9h') S-67
68 Methyl-2,3-diphenylacrylate (10) S-68
69 Methyl-2,3-diphenylacrylate (11) S-69
70 2-Phenyl-2-(triethylsilyl)ethan-1-ol (12) S-70
71 2-Phenyl-2-(triethylsilyl)ethyl 2-phenylacetate (13) S-71
72 2-Phenyl-2-(triethylsilyl)ethyl 2-diazo-2-phenylacetate (14) S-72
73 (E)-(1,3-Diphenylallyl)triethylsilane (16) S-73
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