Table 4 Screening of carbon-selenium bond formation reaction conditions using heterogeneous catalyst.

From: Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se

Entry

Catalyst (mg)

Solvent

Base (4 mmol)

Temp. (°C)

Yield (%)a,b

1

–

PEG200

KOH

120

N.R

2

50

PEG200

KOH

120

95

3

30

PEG200

KOH

120

94

4

10

PEG200

KOH

120

70

5

30

DMF

KOH

120

65

6

30

DMSO

KOH

120

80

7

30

H2O

KOH

reflux

N.R

8

30

Dioxane

KOH

reflux

N.R

9

30

PEG200

NaOH

120

70

10

30

PEG200

K2CO3

120

75

11

30

PEG200

Na2CO3

120

65

12

30

PEG200

KOH (2 mmol)

120

75

13

30

PEG200

KOH

130

95

14

30

PEG200

KOH

90

80

  1. aReaction conditions: iodobenzene (1 mmol), phenylboronic acid (1 mmol), Se (1.5 mmol), base (4 mmol), catalyst and solvent (2 mL), 2.5 h.
  2. bIsolated yield.
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