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Article << Previous     |     Next >>   Contents Vol 63(7)

Synthetic Methods for the Generation and Preparative Application of Benzyne

Tsugio Kitamura

Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan. Email: kitamura@cc.saga-u.ac.jp
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Many methods have been developed for generating benzyne. Convenient and reliable precursors extensively studied so far involve benzenediazonium-2-carboxylate and o-dihalobenzenes such as 1,2-bromofluorobenzene and 1,2-dibromobenzene. Recently, in addition to the above precursors, o-(trimethylsilyl)phenyl triflate has been put into frequent use for benzyne reactions, in which benzyne is efficiently generated under mild conditions using fluoride ion. Furthermore, o-(trimethylsilyl)phenyliodonium triflate has been developed as a more efficient benzyne precursor. This mini-review focusses on recent progress in benzyne chemistry from the viewpoint of organic synthesis. The methods for generating benzynes are classified by the conditions into four categories: basic conditions using strong bases, mild conditions using fluoride ion, thermolysis, and oxidation.

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