Cross-coupling of E,E-1,4-diiodobuta-1,3-diene
Russ.Chem.Bull., Int.Ed., Vol. 50, No. 11, November, 2001 2099
Found (%): C, 78.75; H, 5.74. C28H24P2. Calculated (%):
C, 79.61; H, 5.76. 1H NMR (CDCl3), δ: 6.40 (m, 2 H,
=CHCH=); 7.31 (m, 20 H, C6H5); 7.65 (m, 2 H, =CHP).
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4
13C NMR (CDCl3), δ: 128.45 (d, JPC = 4.0 Hz); 128.60 (d,
2
3JPC = 23.1 Hz); 133.15 (d, JPC = 18.1 Hz); 137.29 (d,
1
C6H5P, JCP = 9.1 Hz); 133.50 (dd, PC=CC=CP,
2JCP
=
18.11 Hz, 3JPC
=
3.5 Hz); 142.75 (dd,
1
4
PC=CC=CP, JCP = 24.14 Hz, JPC = 12.0 Hz).
The reaction of E,E-1,4-diiodobuta-1,3-diene (1) with
diphenyl(trimethylsilyl)phosphine. A solution of compound 1
(0.306 g, 1 mmol) in benzene (2.5 mL) was placed in a tube.
Then diphenyl(trimethylsilyl)phosphine (0.516 g, 2 mmol) and
bis(triphenylphosphino)palladium dichloride (0.028 g, 4 mol.%)
were added and the tube was sealed. The reaction mixture was
heated at 90100 °C for 9 h. After completion of the reaction,
the solvent was distilled off in vacuo. The target product was
extracted from the crystalline precipitate with a 1 : 1 ben-
zenelight petroleum ether mixture. E,E-1,4-Bis(diphenyl-
phosphino)buta-1,3-diene (6) was obtained in a yield of 0.398 g
(95%), m.p. 142142.5 °C.
The reaction of E,E-1,4-diiodobuta-1,3-diene (1) with
thiophenol. Lithium thiophenoxide (0.26 g, 2.13 mmol), which
was prepared from thiophenol (0.23 g, 2.13 mmol) in THF
(2 mL) and butyllithium in hexane (0.138 g, 1.2 mL,
1.78 mol L1, 2.16 mmol), was added to a solution of com-
pound 1 (0.306 g, 1 mmol) and tetrakis(triphenylphos-
phino)palladium (0.046 g, 4 mol.%) in benzene (5 mL). The
reaction mixture was stored at 20 °C for 2 h. After completion
of the reaction (TLC control, ethanoldichloromethane, 1 : 1),
the solvent was distilled off in vacuo and the residue was
recrystallized from light petroleum ether. E,E-1,4-Bis(phenyl-
thio)buta-1,3-diene (7) was obtained in a yield of 0.24 g
(90%), m.p. 56.357.2 °C. Found (%): C, 70.95; H, 5.23;
S, 23.82. C16H14S2. Calculated (%): C, 71.11; H, 5.19; S, 23.70.
1H NMR (CDCl3), δ: 6.29 (m, 2 H, =CHS); 7.22 (m, 2 H,
=CHCH=); 7.30 (m, 10 H, C6H5). 13C NMR (CDCl3), δ:
125.67 (=CS); 130.44 (=CC=); 127.04, 127.36, 128.96,
136.90 (C6H5).
The reaction of E,E-1,4-diiodobuta-1,3-diene (1) with
tripropyl(phenylthio)stannane. A solution of compound 1 (0.3 g,
1 mmol), tripropyl(phenylthio)stannane (0.7 g, 1.96 mmol),
and tetrakis(triphenylphosphino)palladium (0.057 g, 5 mol.%)
in toluene (2 mL) was kept at 20 °C for 24 h (the completion
of the reaction was determined by TLC). Then the reaction
mixture was intensively washed three times with a solution of
potassium fluoride. The precipitate that formed was filtered
off, the solvent was evaporated from the filtrate, and
the crystalline precipitate was recrystallized from hexane.
E,E-1,4-Bis(phenylthio)buta-1,3-diene (7) was obtained in a
yield of 0.22 g (82%), m.p. 5657 °C.
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This study was financially supported by the Russian
Foundation for Basic Research (Project No. 0003-32747),
by the Program "Leading Scientific Schools" (Project
No. 0015-97406), and by the Program "Integration of
the Higher School and Basic Research" (AO115).
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