An Improved Protocol for the Oxidative Cleavage of Alkynes, Alkenes, and Diols with Recyclable Ru/C

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.

oxidation - Ru/C - supported catalyst - alkenes - alkynes - diols - carboxylic acids

References and Notes

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<A NAME="RG35008ST-16">16</A>

Typical Experimental Procedure for the Oxidation of Alkynes
Ruthenium (1 mol%, Ru/C, 20 mg), alkyne (1 mmol), Oxone (1 equiv), and NaHCO₃ (2.5 equiv) were taken in a round-bottom flask (25 mL) with a magnetic stir bar. Then, a mixture of H₂O-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 Na₂SO₄, 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-H₂O (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 Na₂SO₄, and concentrated to give the analytically pure product.

<A NAME="RG35008ST-17">17</A>

Specific optical rotation of the product (+)-3-methyladipic acid was [α]_D ^²0 7.1 (c 5, MeOH).