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Synlett 2009(5): 739-742  
DOI: 10.1055/s-0028-1087933
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Vijay Kumar A., V. Prakash Reddy, R. Sridhar, B. Srinivas, K. Rama Rao*
Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
e-Mail: kakulapatirama@gmail.com;
Further Information

Publication History

Received 21 October 2008
Publication Date:
25 February 2009 (online)

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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

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16

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.

17

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