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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
Organic & Biomolecular Chemistry Pub Date : 01/26/2011 00:00:00 , DOI:10.1039/C0OB01148G
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.

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