Co(III)-Catalyzed C H Activation: A Site-Selective Conjugate Addition of Maleimide to Indole at the C-2 Position

Transcription

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