Stereoselective Heck Reactions with Vinyl Sulfoxides, Sulfides and Sulfones. Issue 18 (27th November 2013)

• Record Type: Journal Article
• Authors: Bachmann, Daniel G.; Wittwer, Christopher C.; Gillingham, Dennis G.
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 18(2013)
• Page Start: 3703
• Page End: 3707
• Publication Date: 2013-11-27
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300678
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We report the Heck cross‐coupling of notoriously unreactive, but synthetically valuable olefins: vinyl sulfoxides, vinyl sulfones, and vinyl sulfides. Key findings include the importance of the sterically hindered (tri‐<italic>tert‐</italic>butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, <italic>E</italic>‐selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t37wcbm" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>