Co(III)-Catalyzed C H Activation: A Site-Selective Conjugate Addition of Maleimide to Indole at the C-2 Position
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1 Supporting Information Co(III)-Catalyzed C H Activation: A Site-Selective Conjugate Addition of Maleimide to Indole at the C-2 Position Nachimuthu Muniraj and Kandikere Ramaiah Prabhu* Department of Organic Chemistry, Indian Institute of Science, Bangalore , Karnataka, India * prabhu@orgchem.iisc.ernet.in S-1
2 Contents 1 Deuterium labelling studies S H and 13 C NMR spectra for all the products S-5 S-2
3 Deuterium labeling studies: Scheme S1: Deuterium labeling studies In a 8-mL screw cap reaction vial, N-pyrimidinylindole (0.2 mmol), cobalt catalyst (5mol %) and AgOAc (10 mol %), were added followed by the addition of TFE:MeOD(2 ml, 9:1). This vial was sealed with a screw cap, placed in a pre-heated metal block at 100 C for 2 h, cooled to room temperature, and concentrated to yield the crude product, which was further purified by flash chromatography to give the desired product deutrio-1a in 99% yield. The deuterium incorporation was calculated from 1 H NMR spectroscopy (See the following 1 H NMR spectra). S-3
4 ppm ppm Figure S1. 1 H NMR spectra of the compound 1a and deutrio-1a S-4
5 ppm Figure S2. 1 H NMR spectra of the Compound 3aa S-5
6 ppm Figure S3. 13 C NMR spectra of the Compound 3aa S-6
7 ppm Figure S4. 1 H NMR spectra of the Compound 3ba S-7
8 ppm Figure S5. 13 C NMR spectra of the Compound 3ba S-8
9 ppm Figure S6. 1 H NMR spectra of the Compound 3ca S-9
10 ppm Figure S7. 13 C NMR spectra of the Compound 3ca S-10
11 ppm Figure S8. 1 H NMR spectra of the Compound 3da S-11
12 ppm Figure S9. 13 C NMR spectra of the Compound 3da S-12
13 ppm Figure S10. 1 H NMR spectra of the Compound 3ea S-13
14 ppm Figure S C NMR spectra of the Compound 3ea S-14
15 ppm Figure S12. 1 H NMR spectra of the Compound 3fa S-15
16 ppm Figure S C NMR spectra of the Compound 3fa S-16
17 ppm Figure S14. 1 H NMR spectra of the Compound 3ga S-17
18 ppm Figure S C NMR spectra of the Compound 3ga S-18
19 ppm Figure S16. 1 H NMR spectra of the Compound 3ha S-19
20 ppm Figure S C NMR spectra of the Compound 3ha S-20
21 ppm Figure S18. 1 H NMR spectra of the Compound 3ia S-21
22 ppm Figure S C NMR spectra of the Compound 3ia S-22
23 ppm Figure S20. 1 H NMR spectra of the Compound 4ab S-23
24 ppm Figure S C NMR spectra of the Compound 4ab S-24
25 ppm Figure S22. 1 H NMR spectra of the Compound 4ac S-25
26 ppm Figure S C NMR spectra of the Compound 4ac S-26
27 ppm Figure S24. 1 H NMR spectra of the Compound 4ad S-27
28 ppm Figure S C NMR spectra of the Compound 4ad S-28
29 ppm Figure S26. 1 H NMR spectra of the Compound 4ae S-29
30 ppm Figure S C NMR spectra of the Compound 4ae S-30
31 ppm Figure S28. 1 H NMR spectra of the Compound 4af S-31
32 ppm Figure S C NMR spectra of the Compound 4af S-32
33 ppm Figure S30. 1 H NMR spectra of the Compound 4bb S-33
34 ppm Figure S C NMR spectra of the Compound 4bb S-34
35 ppm Figure S32. 1 H NMR spectra of the Compound 4bc S-35
36 ppm Figure S C NMR spectra of the Compound 4bc S-36
37 ppm Figure S34. 1 H NMR spectra of the Compound 4bd S-37
38 ppm Figure S C NMR spectra of the Compound 4bd S-38
39 ppm Figure S36. 1 H NMR spectra of the Compound 4cb S-39
40 ppm Figure S C NMR spectra of the Compound 4cb S-40
41 ppm Figure S38. 1 H NMR spectra of the Compound 4cc S-41
42 ppm Figure S C NMR spectra of the Compound 4cc S-42
43 ppm Figure S40. 1 H NMR spectra of the Compound 4cd S-43
44 ppm Figure S C NMR spectra of the Compound 4cd S-44
45 ppm Figure S42. 1 H NMR spectra of the Compound 5 S-45
46 ppm Figure S C NMR spectra of the Compound 5 S-46
47 ppm Figure S44. 1 H NMR spectra of the Compound 7aa S-47
48 ppm Figure S C NMR spectra of the Compound 7aa S-48
49 ppm Figure S46. 1 H NMR spectra of the Compound 7ba S-49
50 ppm Figure S C NMR spectra of the Compound 7ba S-50
51 O N N O N N 7ca 1 H(CDCl3,400MHz) ppm Figure S48. 1 H NMR spectra of the Compound 7ca S-51
52 ppm Figure S C NMR spectra of the Compound 7ca S-52
53 ppm Figure S50. 1 H NMR spectra of the Compound 7ca S-53
54 ppm Figure S C NMR spectra of the Compound 7ca S-54
55 O N N O N N 8 O OEt 1 H(CDCl3,400MHz) ppm Figure S52. 1 H NMR spectra of the Compound 8 S-55
56 O N N O N N 8 O OEt 13 C(CDCl3,100MHz) ppm Figure S C NMR spectra of the Compound 8 S-56
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