Gold-Catalyzed Cyclotrimerization of Arynes for the Synthesis of Triphenylenes

来源 :第五届岭南有机化学论坛暨华南理工大学-兰州大学有机化学双边论坛 | 被引量 : 0次 | 上传用户:teddycici
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Aryne chemistry has been of particular interest due to its high reactivity and broad applications in organic synthesis.Recently,transition metal-catalyzed reactions involving arynes,which are generated by fluoride-induced elimination of Kobayashis silylaryl triflate under mild conditions,have been well documented.Since Guiti n and co-workers first reported Pd(0)-catalyzed cyclotrimerization of arynes to generate triphenylenes in 1998,a variety of important triphenylene derivatives,which demonstrated potent applications in organic materials,have been prepared under similar reaction conditions.Most recently,our group developed a novel Au(Ⅲ)-catalyzed tetramerization of terminal electron-deficient alkynes to afford 1,2,5,6-tetrasubstituted-cyclooctatetraene(1,2,5,6-COT).We have been interested in studying gold-catalyzed cyclotrimerization of arynes(active π-components),which have seldom served as the substrate for gold catalysis.Herein,we report that the use of PPh3AuCl as the catalyst for the cyclotrimerization of arynes provides a convenient and general approach to triphenylenes under mild conditions.(Scheme 1).
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