A highly efficient microwave-assisted suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids.
[reaction: see text] A new strategy to improve the efficiency of Suzuki coupling reactions is introduced by combining fast microwave reaction with easy fluorous separation. Aryl perfluorooctylsulfonates derived from the corresponding phenols are coupled with aryl boronic acids to form biaryls under general microwave conditions. Both intermediates and products are purified by solid-phase extraction over FluoroFlash silica gel. Application of this tagging strategy to multistep synthesis of biaryl-substituted hydantoin is also described.
Zhang
Wei
W
Fluorous Technologies, Inc., University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA. w.zhang@flourous.com
Chen
Christine Hiu-Tung
CH
Lu
Yimin
Y
Nagashima
Tadamichi
T
D017738:Alkanesulfonic Acids / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D008872:Microwaves; D015394:Molecular Structure; D013431:Sulfates / Q000138:chemical synthesis*
D017738:Alkanesulfonic Acids; D001897:Boronic Acids; D005466:Fluorocarbons; D006845:Hydrocarbons, Fluorinated; D013431:Sulfates; C076994:perfluorooctane sulfonic acid