Direct arylation of oligonaphthalenes using PIFA/BF3· Et2O: From double arylation to larger oligoarene products

Wusheng Guo, Enrico Faggi, Rosa M. Sebastián, Adelina Vallribera, Roser Pleixats, Alexandr Shafir

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

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. © 2013 American Chemical Society.
Original languageEnglish
Pages (from-to)8169-8175
JournalJournal of Organic Chemistry
Volume78
Issue number16
DOIs
Publication statusPublished - 16 Aug 2013

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