Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes

Ana B. Cuenca, Sergi Montserrat, Kabir M. Hossain, Gisela Mancha, Agustí Lledós, Mercedes Medio-Simón, Gregoři Ujaque, Gregorio Asensio

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103 Citations (Scopus)

Abstract

The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 In good yields. Unpredictably, In all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom Is obtained Instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations Is proposed to account for the products In this lntermolecular gold(l)-catalyzed reaction. © 2009 American Chemical Society.
Original languageEnglish
Pages (from-to)4906-4909
JournalOrganic Letters
Volume11
Issue number21
DOIs
Publication statusPublished - 5 Nov 2009

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