Stereocontrolled access to unsymmetrical 1,1-diaryl-2-fluoroethenes.
A simple and effective method for stereocontrolled preparation of 1,1-diaryl-2-fluoroethenes is reported. First, 1-aryl-1-bromo-2-fluoroethenes are generated using an addition/elimination reaction of hydride to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction. Subsequent Suzuki-Miyaura coupling with a variety of boronic acids gives access to the desired 1,1-diaryl-2-fluoroethenes.
Landelle
Grégory
G
Canada Research Chair in Organic and Medicinal Chemistry, Dpartement de chimie, 1045 avenue de la Médecine, Université Laval, Québec, QC, Canada G1V 0A6.
Turcotte-Savard
Marc-Olivier
MO
Marterer
Judikaëlle
J
Champagne
Pier Alexandre
PA
Paquin
Jean-François
JF
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry
D001897:Boronic Acids; D005030:Ethylenes; D006845:Hydrocarbons, Fluorinated; D012821:Silanes