Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes.
An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.
Landelle
Grégory
G
Canada Research Chair in Organic and Medicinal Chemistry, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, QC, Canada G1V 0A6.
Champagne
Pier Alexandre
PA
Barbeau
Xavier
X
Paquin
Jean-François
JF
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D012821:Silanes; D010165:Palladium