Table 1 Optimization of catalytic amination conditionsa.

From: Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism

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Entry

Variation of standard conditions

Yield (%)b

1

None

92 (91c)

2

L2 instead of L1

37

3

L3 instead of L1

66

4

L4 instead of L1

63

5

L5 instead of L1

27

6

FeCl3 instead of FeI2

7

7

Fe(acac)3 instead of FeI2

nd

8

PhSiH3 instead of (EtO)3SiH

79

9

Without 4CzIPN

59 (88d)

10

Without FeI2

nd

11

Without light irradiation

nd

  1. nd not detected, blue LED blue light-emitting diode.
  2. aStandard conditions: 4CzIPN (1 mol%), FeI2 (10 mol%), L1 (10 mol%), 1 (0.6 mmol), 2 (0.2 mmol), 2,6-lutidine (3.0 equiv.), (EtO)3SiH (2.0 equiv.), MeCN (2 mL), blue LEDs, 65 °C, 24 h.
  3. bGC yield. cIsolated yield.
  4. dTime = 44 h. See Supplementary Information for additional optimization experiments.