Table 1 Optimization of the reaction conditions[a]

From: Electrochemical selective hydrocarboxylation of acrylamides with carbon dioxide for precise control of α- and β-carboxylation

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Entry

Anode/Cathode

Electrolyte

Solvent

T.

Yield (%)[d]

2a

3a

1

Mg/C

TBAC

DMF

R.T.

80 (70)[e]

-

2

Al/C

TBAC

DMF

R.T.

51

-

3

Zn/C

TBAC

DMF

R.T.

26

-

4

C/C

TBAC

DMF

R.T.

39

-

5

Mg/C

TBAI

DMF

R.T.

45

-

6

Mg/C

TBABF4

DMF

R.T.

63

-

7

Mg/C

TBAPF6

DMF

R.T.

33

-

8

Mg/C

TBAClO4

DMF

R.T.

55

-

9

Mg/C

TBAC

DMAC

R.T.

72

-

10

Mg/C

TBAC

NMP

R.T.

52

-

11

Mg/C

TBAC

DMSO

R.T.

47

6

12

Mg/C

TBAC

CH3CN

R.T.

62

14

13[b]

Mg/C

TBAB

CH3CN

R.T.

20

13

14[b]

Mg/C

TBAI

CH3CN

R.T.

11

7

15[b]

Mg/C

TBABF4

CH3CN

R.T.

13

16

16[b]

Mg/C

TBAPF6

CH3CN

R.T.

16

14

17[b]

Mg/C

TBAClO4

CH3CN

R.T.

-

18

18[b]

Mg/C

TEAClO4

CH3CN

R.T.

-

37

19[b][c]

Mg/C

TEAClO4

CH3CN

R.T.

-

46

20[b][c]

Mg/C

TEAClO4

CH3CN

0 °C

-

64

21[b][c]

Mg/C

TEAClO4

CH3CN

-10 °C

-

77 (70)[e]

22[b][c]

Mg/C

TEAClO4

CH3CN

-20 °C

-

73

23

Mg/C

TBAC

DMF

-10 °C

76

-

  1. [a] Reaction conditions: undivided cell, Mg plate anode (10 mm × 20 mm × 0.5 mm), C plate cathode (10 mm × 20 mm × 1.0 mm), 1a (0.2 mmol), electrolyte (0.2 mmol), CO2 (1 atm), solvent (3.0 mL), 8 mA, 3.5 h, room temperature (R.T.). [b] 6 mA. [c] 1a (0.1 mmol). [d] The yield was determined by 1H NMR using maleic acid as the internal standard. [e] Isolated yield. DMF=N, N-dimethylformamide, DMSO dimethyl sulfoxide, CH3CN acetonitrile, NMP N-methyl-2-pyrrolidone, DMAC=N, N-dimethylacetamide, TBAC tetrabutylammonium chloride, TBAI tetrabutylammonium iodide, TBAB tetrabutylammonium bromide, TB0AClO4 tetrabutylammonium perchlorate, TBABF4 tetrabutylammonium tetrafluoroborate, TBAPF6 tetrabutylammonium hexafluorophosphate.