Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylation of Arenes
Organic Letters2009Vol. 11(21), pp. 4906–4909
Citations Over TimeTop 10% of 2009 papers
Ana B. Cuenca, Sergi Montserrat, Kabir M. Hossain, Gisela Mancha, Agustı́ Lledós, Mercedes Medio‐Simón, Gregori Ujaque, Gregorio Asensio
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 intermolecular gold(I)-catalyzed reaction.
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