Benzyl radical addition reaction through the homolytic cleavage of a benzylic C–H bond

Masafumi Ueda; Eiko Kondoh; Yuta Ito; Hiroko Shono; Maiko Kakiuchi; Yuki Ichii; Takahiro Kimura; Tetsuya Miyoshi; Takeaki Naito; Okiko Miyata

doi:10.1039/C0OB01148G

Benzyl radical addition reaction through the homolytic cleavage of a benzylic C–H bond†‡

Masafumi Ueda,^a Eiko Kondoh,^a Yuta Ito,^a Hiroko Shono,^a Maiko Kakiuchi,^a Yuki Ichii,^a Takahiro Kimura,^a Tetsuya Miyoshi,^a Takeaki Naito^a and Okiko Miyata*^a

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^a Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe, Japan
E-mail: miyata@kobepharma-u.ac.jp
Fax: +81-78-441-7556

Abstract

Direct generation of a benzyl radical by C–H bond activation of toluenes and the addition reaction of the resulting radical to an electron deficient olefin were developed. The reaction of dimethyl fumarate with toluene in the presence of Et₃B as a radical initiator at reflux afforded 2-benzylsuccinic acid dimethyl ester in good yield.

This article is part of the themed collection: Free Radical Chemistry special themed issue in memory of Athel Beckwith

Organic & Biomolecular Chemistry

Benzyl radical addition reaction through the homolytic cleavage of a benzylic C–H bond†‡

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Benzyl radical addition reaction through the homolytic cleavage of a benzylic C–H bond

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