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Metal Catalyzed Cross-Coupling
Reactions
Diederich F.
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19
Synthesis of the
Fe
3
O
4
nanoparticles:
FeSO4˙7H2O (13.9 g) and Fe2
(SO4)3 (20
g) were dissolved in H2O (500 mL) in a 1000 mL beaker.
NH4OH (aq, 25%) was added slowly to adjust the
pH of the solution to 10. The reaction mixture was then continually
stirred for 1 h at 60 ˚C. The precipitated nanoparticles
were separated magnetically, washed with water until the pH 7,
and then dried under vacuum at 60 ˚C for 2 h.
This magnetic nano ferrite (Fe3O4) was then
used for the preparation of Pd/Fe3O4.
Synthesis of the Pd/Fe
3
O
4
catalyst:
Fe3O4 nanoparticles were impregnated with
Na2PdCl4 (1.0%) aqueous solution and
stirred for 1 h. After impregnation, the suspension was adjusted
to pH 12 by adding NaOH (1 M) and stirred for 6 h. The
solid was washed with distilled H2O. The catalyst precursors
were reduced by adding 0.2 M NaBH4 solution dropwise
under gentle stirring in an ice-water bath for 30 min
until no obvious bubbles were observed in the solution. The resulting
Pd/Fe3O4 was washed thoroughly with
distilled H2O and subsequently with EtOH. The palladium
content in the catalyst was measured as 0.023 mmol˙g-¹ using
ICP-AES.
General procedure for the
Hiyama reaction: A mixture
of aryl bromide (1 mmol),
aryl siloxane (1.2 mmol), NaOH (3 mmol), Pd/Fe3O4 catalyst
(50 mg, 0.2 mol% of Pd) and distilled H2O (3
mL) was taken in a round-bottomed flask and stirred at 90 ˚C
for 6 h. After completion of the reaction (monitored by
TLC) the catalyst was easily separated from the reaction mixture
with an external magnet. After removing the solvent, the crude material
was purified by chromatography on silica gel to afford the pure
product. The spectroscopic data of all known compounds were identical
to those reported in the literature.
2′-Methoxy-4-methylbiphenyl (Table
[²]
, entry 8): ¹H
NMR (300 MHz, CDCl3): δ = 2.35 (s,
3 H), 3.78 (s, 3 H), 6.88-6.99 (m, 2 H),
7.22-7.28 (m, 2 H), 7.15 (d, J = 8.0
Hz, 2 H), 7.35 (d, J = 8.0 Hz,
2 H). ¹³C NMR (75 MHz, CDCl3): δ = 21.1,
55.4, 111.1, 120.7, 128.3, 128.6, 129.3, 130.7, 131.4, 131.5, 136.4,
156.4. MS (EI): m/z = 198 [M]+.
4′-Methoxy-2,4,6-trimethylbiphenyl (Table
[²]
, entry 16): ¹H
NMR (300 MHz, CDCl3): δ = 2.03 (s,
6 H), 2.35 (s, 3 H), 3.86 (s, 3 H), 6.95
(s, 2 H), 7.07 (d, J = 8.6 Hz,
2 H), 7.49 (d, J = 8.6 Hz, 2 H). ¹³C
NMR (75 MHz, CDCl3): δ = 20.7, 20.9, 55.2,
113.7, 127.9, 130.3, 133.2, 136.4, 138.6, 158.1. MS (EI): m/z = 226 [M]+.
4′-tert-Butyl-2,4,6-trimethylbiphenyl (Table
[²]
, entry 17): ¹H
NMR (300 MHz, CDCl3): δ = 1.39 (s,
9 H), 1.98 (s, 6 H), 2.30 (s, 3 H), 6.85
(s, 2 H), 7.01 (d, J = 8.3 Hz,
2 H), 7.41 (d, J = 8.3 Hz, 2 H). ¹³C
NMR (75 MHz, CDCl3): δ = 20.8, 27.0, 31.3,
34.4, 125.6, 126.6, 127.9, 128.8, 136.2, 138.2, 149.8. MS (EI):
m/z = 252 [M]+.
1-p-Tolylnaphthalene (Table
[²]
, entry 18): ¹H
NMR (300 MHz, CDCl3): δ = 2.45 (s,
3 H), 7.25 (d, J = 8.3 Hz, 2 H), 7.33-7.38
(m, 3 H), 7.39-7.49 (m, 3 H), 7.77-7.92
(m, 3 H). ¹³C NMR (75 MHz,
CDCl3): δ = 21.2, 125.3, 125.6, 125.8, 126.0,
126.8, 127.4, 128.2, 128.9, 129.9, 131.6, 133.7, 136.8, 137.7, 140.2.
MS (ESI): m/z = 218 [M]+.