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A One-Pot, Transition-Metal-Free Procedure for C-O, C-S, and C-N Bond Formation at the Benzylic Position of Methylarenes

Hiroyuki Shimojo, Katsuhiko Moriyama, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2015, 47, 1280-1290.

DOI: 10.1055/s-0034-1380069 (free Supporting Information)


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Abstract

Treatment of methylarenes with 1,3-dibromo-5,5-dimethylhydantoin or N-bromosuccinimide and a catalytic amount of 2,2′-azobis(isobutyronitrile) followed by a reaction with a nucleophile, such as benzoic acid, p-toluenethiol, sodium p-toluenesulfinate, aqueous dimethylamine, or succinimide, provides the corresponding benzylated products in good yields.

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Key Words

methylarenes, Wohl-Ziegler reaction, 1,3-dibromo-5,5-dimethylhydantoin, esters, benzyl amines, benzyl sulfides, benzyl sulfones


ID: J66-Y2015