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Stereoselective Heck Reactions with Vinyl Sulfoxides, Sulfides and Sulfones
Author(s) -
Bachmann Daniel G.,
Wittwer Christopher C.,
Gillingham Dennis G.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300678
Subject(s) - chemistry , phosphine , triethylamine , heck reaction , steric effects , organic chemistry , stereoselectivity , ligand (biochemistry) , palladium , catalysis , biochemistry , receptor
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‐ tert‐ butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, E ‐selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry.