title: Pd-catalyzed cross-coupling of potassium alkenyltrifluoroborates with 2-chloroacetates and 2-chloroacetamides.
abstract: A protocol for the stereocontrolled synthesis of (E)- and (Z)-β,γ-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling reaction with potassium (E)- and (Z)-alkenyltrifluoroborates, affording the corresponding products in high yield.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Thiago
authors.initials: T
authors.lastname: Barcellos
authors.forename: Kaitlin M
authors.initials: KM
authors.lastname: Traister
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D000475:Alkenes; D001881:Borates; D062845:Chloroacetates; D006846:Hydrocarbons, Halogenated; D010165:Palladium; D011188:Potassium