Gold-Catalyzed Direct Arylation

Liam T Ball, Guy C Lloyd-Jones, Chris A Russell

Research output: Contribution to journalArticle (Academic Journal)peer-review

235 Citations (Scopus)

Abstract

Biaryls (two directly connected aromatic rings, Ar1-Ar2) are common motifs in pharmaceuticals, agrochemicals, and organic materials. Current methods for establishing the Ar1-Ar2 bond are dominated by the cross-coupling of aryl halides (Ar1-X) with aryl metallics (Ar2-M). We report that, in the presence of 1 to 2 mole percent of a gold catalyst and a mild oxidant, a wide range of arenes (Ar1-H) undergo site-selective arylation by arylsilanes (Ar2-SiMe3) to generate biaryls (Ar1-Ar2), with little or no homocoupling (Ar1-Ar1/Ar2-Ar2). Catalysis proceeds at room temperature and tolerates a broad range of functional groups, including those incompatible with cross-coupling. These features expedite biaryl preparation, as demonstrated by synthesis of the nonsteroidal anti-inflammatory diflunisal.
Original languageEnglish
Pages (from-to)1644-1648
Number of pages5
JournalScience
Volume337
Issue number6102
DOIs
Publication statusPublished - 28 Sep 2012

Structured keywords

  • BCS and TECS CDTs

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