Table 5 Preparation of biphenyl derivative from Suzuki reaction using Pd-BisPyP@bilayer-SiO2@NMPa.

From: Palladium anchored to BisPyP@bilayer-SiO2@NMP organic–inorganic hybrid as an efficient and recoverable novel nanocatalyst in suzuki and stille C–C coupling reactions

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Entry

R

X

Time (min)

Yield (%)b

M.p. (°C)

TOF (min−1)c

Found

Reported

1

H

I

5

98

68–70

68–7058

18.490

2

4-OCH3

I

8

95

87–89

88–9058

11.202

3

4-CH3

I

6

97

45–47

44–4658

15.251

4

2-CO2H

I

11

97

107–109

107–10959

8.319

5

H

Br

7

96

68–70

68–7058

12.938

6

4-CH3

Br

9

98

45–47

44–4658

10.272

7

4-OH

Br

10

98

161–163

163–16460

9.245

8

4-CHO

Br

12

97

55–57

54–5661

7.265

9

4-CN

Br

13

97

84–86

85–8660

7.039

10

4-CO2H

Br

13

94

226–228

224–22862

6.821

11

4-NO2

Br

9

97

111–113

112–11458

10.167

12

4-NH2

Br

10

97

51–53

50–5361

9.150

13

4-SH

Br

11

95

109–111

110–11163

8.147

14

3-CHO

Br

10

94

52–54

53–5464

8.867

15

4-Cl

Br

10

95

71–73

71–7365

8.962

16

H

Cl

15

94

162–164

163–16460

5.911

  1. aReaction conditions: aryl halide (1 mmol), PhB(OH)2 (1 mmol), base (3 mmol), Pd-BisPyP@bilayer-SiO2@NMP (5 mg, 1.06 mol%), PEG-400 (2 mL).
  2. bIsolated yield.
  3. cTurnover frequency.
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