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Synthesis of α-Keto Acids via Oxidation of Alkenes Catalyzed by a Bifunctional Iron Nanocomposite

Tao Song, Zhiming Ma, Xiaoxue Wang and Yong Yang*

*CAS Key Laboratory of Bio-Based Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China, Email: yangyongqibebt.ac.cn

T. Song, Z. Ma, X. Wang, Y. Yang, Org. Lett., 2021, 23, 5917-5921.

DOI: 10.1021/acs.orglett.1c02021


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Abstract

A recyclable, bifunctional iron nanocomposite catalyzes an efficient synthesis of α-keto acids via oxidation of alkenes using TBHP as oxidant. A variety of alkenes with different functional groups were smoothly oxidized into their corresponding α-keto acids in good yields.

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proposed mechanism

recycling performance of catalyst



General procedures for the synthesis of α-keto acids

A 25 mL sealing tube was charged with a magnetic stirring, alkenes (0.2 mmol), Fe@NCP-800 (20 mg, 10 mol% of Fe), tBuOOH 70wt% in water (Mw = 90.18, 121 μL, 1.0 mmol, 5 eq.), TBAI (Mw = 369.37, 22.1 mg, 0.06 mmol, 30 mol%), CH3CN/H2O (2 mL, 20/1 v/v). The reaction was stirred for 12 h at 90 C in an oil bath. After completion of the reaction, the reaction mixture was cooled to room temperature and the liquid was extracted by ethyl acetate and the organic phase was analyzed by NMR and GC-MS. The products were purified by silica gel column (DCM/EtOH = 20:1, 15:1, 10:1 or 5:1) and structurally confirmed by NMR.


Key Words

α-keto carboxylic acids, TBHP


ID: J54-Y2021