B. Barati et al. / Inorganic Chemistry Communications 29 (2013) 114–117
117
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Table 3
Comparison of the results obtained with [RuHCl(CO)(PPh3)3]/styrene oxide catalytic
system with some of those reported in the literature.
Catalyst
Catalyst
amount
Yield (%)
Time (h)
Ref.
[RuHCl(CO)(PPh3)3]/DPSO
CuCl/tBuOOH
PS-TEMPO/NaClO
Pt-C/Air
TPAP/NMO
KMnO4
4 mol%
5 mol%
10 mol%
1.95 wt.%
10 mol%
4 mmol
4 wt.%
76–93
76–99
77–98
99
26–100
5–91
2.5
Present work
[10]
[6]
[9]
[11]
[34]
[35]
[36]
1–6
20–48
1–16
–
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catalyzed coupling reaction of arylboronic acids with aryl aldehydes, Chem. Lett.
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Commun. (2009) 6741–6743.
4–18
–
OsO4
CAN
50–85
42–95
2.2 eq
4
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sp3 C\C bond formation via cooperation of Lewis acid-promoted/Rh-catalyzed C\H
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Acknowledgment
The authors gratefully acknowledge financial support from the
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employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents,
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Center of Excellence of Chemistry of University of Isfahan (CECUI).
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[37] General information. Melting point was measured using Stuart Scientific SMP2 appa-
ratus in sealed capillary and not corrected. Solvents and liquid alcohols were dis-
tilled prior to use. The products were purified by silica gel chromatography
(Merck KGaA, Silica Gel 60).1H and 13C NMR (400 and 100 MHz) spectra were
recorded on a Bruker-Avance 400 MHz spectrometer. FT-IR spectra were recorded
on a Nicolet-Impact 400D instrument in the range 400–4000 cm−1. Mass spectra
were recorded on a Platform II spectrometer from Micromass; EI mode at 70 eV. El-
emental analysis was done on a LECO, CHNS-932 analyzer.
Typical procedure for the ruthenium hydride-catalyzed direct oxidation of alcohols to
carboxylic acids with diphenyl sulfoxide: Benzyl alcohol 1a (108.1 mg, 1 mmol),
diphenyl sulfoxide 2 (202.3 mg, 1 mmol), [RuHCl(CO)(PPh3)3] (39.1 mg, 0.04 mmol)
and THF (2 mL) were placed in a screw capped test tube. The test tube was purged
with argon and sealed. The mixture was stirred at 70 °C for 2.5 h. After the reaction
was completed, the solvent was removed under reduce pressure. The residue was pu-
rified by silica gel chromatography (petroleum ether/ethyl acetate=6/1) and
recrystallized from H2O–methanol to give the compound 3a as a white crystal.