Table 6 Preparation of biphenyl derivative from Stille 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

7

98

68–70

68–7058

13.207

2

4-OCH3

I

9

92

87–89

88–9058

9.643

3

4-CH3

I

10

97

45–47

44–4658

9.150

4

H

Br

8

98

68–70

68–7058

11.556

5

4-CH3

Br

14

97

45–47

44–4658

6.536

6

4-OH

Br

10

96

161–163

163–16460

9.056

7

4-CHO

Br

18

93

55–57

54–5661

4.874

8

4-CN

Br

11

98

84–86

85–8660

8.404

9

H

Cl

20

90

162–164

163–16460

4.245

10

4-Cl

Br

12

90

71–73

71–7365

7.075

  1. aReaction conditions: aryl halide (1 mmol), Ph3SnCl (0.5 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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