Abstract
Efficient synthesis of carboxylic acids from alkynes; aldehydes
from alkenes and diols employing Ru/C-based recyclable catalytic
system is reported with good to excellent yields.
Key words
oxidation - Ru/C - supported catalyst - alkenes - alkynes - diols - carboxylic
acids
References and Notes
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16
Typical Experimental
Procedure for the Oxidation of Alkynes
3 (2.5 equiv) were taken in a round-bottom
flask (25 mL) with a magnetic stir bar. Then, a mixture of H2 O-MeCN
(1:1, 5 mL) was added and stirred until complete consumption of
the alkyne was observed as monitored by TLC. The reaction mixture
was extracted with EtOAc (3 × 10 mL),
the combined organic layers were dried over anhyd Na2 SO4 ,
and concentrated to give the analyti-cally pure product.Typical Experimental Procedure for the Oxidation
of Alkenes and Diols
Ruthenium (1 mol%, Ru/C,
20 mg), alkene/diol (1 mmol), and NaIO4 (214
mg, 1.1 equiv), were taken in a mixture EtOAc-MeCN-H2 O
(1:1:1, 4.5 mL) in a 25 mL round-bottom flask with a magnetic stir
bar and stirred until complete consumption of the alkene/diol
was observed as monitored by TLC. The reaction mixture was extracted
with EtOAc (3 × 10 mL), the combined
organic layers were dried over anhyd Na2 SO4 ,
and concentrated to give the analytically pure product.
17 Specific optical rotation of the product
(+)-3-methyladipic acid was [α]D
²0 7.1
(c 5, MeOH).
