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*

*Corresponding author for this work

Research output: Indexed journal article Articlepeer-review

119 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.

Original languageEnglish
Pages (from-to)4906-4909
Number of pages4
JournalOrganic Letters
Volume11
Issue number21
DOIs
Publication statusPublished - 5 Nov 2009
Externally publishedYes

Fingerprint

Dive into the research topics of 'Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes'. Together they form a unique fingerprint.

Cite this