Direct Arylation of Oligonaphthalenes Using PIFA/BF3路Et2O: From Double Arylation to Larger Oligoarene Products

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• 作者：Wusheng Guo ; Enrico Faggi ; Rosa M. Sebasti谩n ; Adelina Vallribera ; Roser Pleixats ; Alexandr Shafir
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：78
• 期：16
• 页码：8169-8175
• 全文大小：397K
• 年卷期：v.78,no.16(August 16, 2013)
• ISSN：1520-6904

文摘

Direct dehydrogenative coupling between the linear ter- and quaternaphthalenes and substituted benzenes was achieved under the Kita conditions using the hypervalent PIFA/BF₃ reagent. Products resulting from either the double arylation of the naphthalenic substrate or the formal dimerizative arylation have been prepared. For example, in the latter mode, ternaphthalene was converted into a series of linear octiarenes (counting the capping Ar). The process represents an alternative to the cross-coupling methodologies employed in related syntheses and proceeds via a selective functionalization of six relatively inert aromatic CH bonds.