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Aerobic Photooxidation of Toluene Derivatives into Carboxylic Acids with Bromine-Water under Catalyst-Free Conditions

Masayuki Kirihara* , Yugo Sakamoto, Sho Yamahara, Atsuhito Kitajima, Naoki Kugisaki, Yoshikazu Kimura*

*Shizuoka Institute of Science and Technology, Shizuoka 437-8555; Iharanikkei Chemical Industry Co. Ltd., Shizuoka 421-3203, Japan, Email: kirihara.masayukisist.ac.jp, kimura.yoshikazuiharanikkei.co.jp

M. Kirihara, Y. Sakamoto, S. Yamahara, A. Kitajima, N. Kugisaki, Y. Kimura, Synlett, 2022, 33, 1670-1674.

DOI: 10.1055/a-1887-7885


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Abstract

Photoirradiation of toluene derivatives with two equivalents of bromine in benzotrifluoride-water provides benzoic acid derivatives in good yields using either a fluorescent lamp, blue LEDs (454 nm), or UV LEDs (385 nm). The reaction might proceed through dibromination of benzylic carbon, generation of the benzylic radical via oxidative C-H abstraction, formation of benzoyl bromide, and hydrolysis.


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Key Words

oxidation, toluene, benzoic acids, carboxylic acid, bromine, oxygen, photochemistry


ID: J72-Y2022