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RESEARCH FRONT
Contents Vol 63(7)

Synthetic Methods for the Generation and Preparative Application of Benzyne

Tsugio Kitamura A
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A 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




Tsugio Kitamura was born in Nagasaki, Japan, in 1954. He received his Ph.D. from Kyushu University in 1982 under the direction of Professor Hiroshi Taniguchi. He joined the faculty as an Assistant Professor at Kyushu University in 1982 and was promoted to an Associate Professor in 1993. From 1986 to 1988, he worked as a postdoctoral fellow with Professor Peter J. Stang at the University of Utah, USA. In 2002, he moved to Saga University as a Professor. His research interests are in the areas of synthetic organic chemistry, including vinyl cations, hypervalent iodines, and transition-metal catalysts.

Australian Journal of Chemistry 63(7) 987-1001 https://doi.org/10.1071/CH10072
Submitted: 9 February 2010  Accepted: 23 March 2010   Published: 15 July 2010

Abstract

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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