Table 1 Optimization of the Reaction Conditions

From: Bench-stable azidodifluoromethyl imidazolium reagents unlock the synthetic potential of carbonimidic difluorides

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Entry

PC (3%)

Solvent

Light intensity

Reagent

Yielda

(isolated)

1

fac-Ir(ppy)3

DCM (0.1 M)

30 W

IMADF-1

30%

s2

Ir(piq)3

DCM (0.1 M)

30 W

IMADF-1

40%

3

Ir[dF(CF3)ppy]2(dtbpy)PF6

DCM (0.1 M)

30 W

IMADF-1

<5%

4

Ir(Fppy)3

DCM (0.1 M)

30 W

IMADF-1

26%

5

4CzIPN

DCM (0.1 M)

30 W

IMADF-1

13%

6

Ir(piq)3

DCM (0.1 M)

30 W

IMADF-2

24%

7

Ir(piq)3

DCM (0.1 M)

30 W

IMADF-3

13%

8

Ir(piq)3

DCM (0.1 M)

30 W

IMADF-4

trace

9

Ir(piq)3

DCM (0.05 M)

30 W

IMADF-1

55%

10

Ir(piq)3

DCM (0.033 M)

30 W

IMADF-1

60%

11b

Ir(piq)3

DCM (0.033 M)

30 W

IMADF-1

61%

12b

Ir(piq)3

DCM (0.05 M)

30 W

IMADF-1

61%

13b

Ir(piq)3

DCM (0.05 M)

60 W

IMADF-1

72%

14b

Ir(piq)3

DCM (0.05 M)

90 W

IMADF-1

78% (72%)

15b

Ir(piq)3

DCM (0.05 M)

–

IMADF-1

0%

16b

–

DCM (0.05 M)

90 W

IMADF-1

trace

  1. Reaction conditions: 1a (0.1 mmol), IMADF (0.15 mmol), PC (0.003 mmol), solvent, blue LED, 12 h under Ar.
  2. DCM dichloromethane, IMADF azidodifluoromethyl imidazolium reagent, PC photocatalyst.
  3. aGC-MS yield with n-dodecane as the internal standard.
  4. b1a (0.2 mmol), IMADF (0.3 mmol), PC (0.006 mmol), solvent, blue LED, 12 h under Ar. Isolated yield in parentheses.
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