title: Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins.
abstract: Simple, mild, and efficient conditions are reported for a Pd(0)-catalyzed Heck reaction that delivers high yields and selectivity for (E)-styrenyl products using electronically nonbiased olefin substrates bearing a range of useful functionality. Preliminary mechanistic studies demonstrate that the σ-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes between β-hydrogens on the basis of their relative hydridic character, in contrast to previously reported Pd(II)-catalyzed oxidative reaction conditions.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors.forename: Erik W
authors.initials: EW
authors.lastname: Werner
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D055601:Organic Chemistry Phenomena; D010165:Palladium; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
chemical_list: D000475:Alkenes; D013343:Styrenes; D010165:Palladium