Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes

Richard J Mudd, Paul Young, James Jordan-Hore, Georgina Margaret Rosair, Ai-Lan Lee

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren’s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.
Original languageEnglish
Pages (from-to)7633-7639
Number of pages7
JournalJournal of Organic Chemistry
Volume77
Issue number17
DOIs
Publication statusPublished - 7 Sep 2012

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