Table 1 Initial studies for the photoinduced reaction of 4-vinyl-1,1’-biphenyl 1a with ethyl chlorooxoacetate 2aa.

From: Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides

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Entry

PS

Solvent

T (oC)

Time

Yield (%)

3a/6ab

1c

Ir(ppy)3

MeCN

40

24 h

NR

2

Ir(ppy)3

MeCN

40

24 h

30

3:1

3

3DPA2FBN

MeCN

40

24 h

22

>20:1

4

Ru(bpy)3Cl2

MeCN

40

6 days

42

14:1

5

Ru(bpy)3Cl2

MeCN

60

72 h

66

11:1

6

Ru(bpy)3Cl2

DMF

60

72 h

13

1:1.3

7

Ru(bpy)3Cl2

DCM

60

72 h

19

7:1

8d

Ru(bpy)3Cl2

MeCN

60

84 h

85

>20:1

9d

MeCN

60

84 h

NR

10d,e

Ru(bpy)3Cl2

MeCN

60

84 h

NR

  1. aReaction conditions: 4-vinyl-1,1’-biphenyl 1a (0.2 mmol), ethyl chlorooxoacetate 2a (0.6 mmol), photocatalyst (0.004 mmol), 2,6-lutidine (0.6 mmol), solvent (4.0 mL), blue LEDs, under N2 atmosphere. Conversion of 1a and the yield of 3a was determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard.
  2. bDetermined by 1H NMR analysis.
  3. cCompound 2a’ was used instead of ethyl chlorooxoacetate 2a.
  4. d2,6-Lutidine (0.3 mmol).
  5. eIn the dark.