Table 1 Optimisation of reaction conditions

From: A scalable photo-mechanochemical platform for sustainable photoredox catalysis by resonant acoustic mixing

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Entry

Variables

Time (min)

Yield (%)a

1

DABCO (2.0 equiv.), Et3N (0.25 equiv.), DMA (0.4 mL)

90

90

2

DABCO (2.0 equiv.), Et3N (0.25 equiv.)

90

87

3

DABCO (2.0 equiv.), Et3N (0.25 equiv.), sea sand (400 mg)

90

82

4

DABCO (2.0 equiv.), Et3N (0.25 equiv.), silica gel (400 mg)

90

43

5

DABCO (2.0 equiv.), Et3N (0.25 equiv.), no light

90

N.R.

6

DABCO (2.0 equiv.), Et3N (0.25 equiv.), no 4CzIPN

90

trace

7

DABCO (2.0 equiv.), Et3N (0.25 equiv.), no NiBr2•glyme

90

N.R.

8

DABCO (2.0 equiv.)

90

trace

9

Et3N (0.25 equiv.)

90

38

10

none

90

N.R.

11

DABCO (1.0 equiv.), Et3N (1.0 equiv.)

30

quant.

12

DABCO (1.0 equiv.), Et3N (1.0 equiv.), NiCl2•6H2O

30

quant.

13

DABCO (1.0 equiv.), Et3N (1.0 equiv.), NiCl2

30

quant.

14

DABCO (1.0 equiv.), Et3N (1.0 equiv.), NiCl2•glyme

30

quant.

15

DABCO (1.0 equiv.), Et3N (1.0 equiv.), NiBr2

30

quant.

16b

DABCO (1.0 equiv.), Et3N (1.0 equiv.)

90

quant.

17

DABCO (1.0 equiv.), Et3N (1.0 equiv.), 2 mmol scale

30

quant.

18

DABCO (1.0 equiv.), Et3N (1.0 equiv.), 5 mmol scale

30

quant.

19

DABCO (1.0 equiv.), Et3N (1.0 equiv.), 2 mmol scale, under air

30

N.R.

  1. aReaction conditions: 0.2 mmol of 1a, 0.4 mmol of 2a, 0.1 mol% of 4CzIPN, and 5 mol% of NiBr2·glyme in a 4 mL glass vial under irradiation of 90 W Aqua Blue LEDs with cooling mechanism (cooling fans and blowing cold air through the vent). The yields were determined by GC-FID with dodecane as the internal standard.
  2. b4-Chlorobenzonitrile 1b was used instead of 1a.