Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates.
[reaction: see text] The design and development of an effective protocol for the palladium-catalyzed cross-coupling of (E)- and (Z)-heptenyldimethylsilanols with organo-triflates and nonaflates is described. Optimization of this coupling focused on the issues of both reactivity and stability of the psuedohalides in the presence of the nucleophilic fluoride promoter for the coupling. The crucial role of varying amounts of water to modulate the reactivity of the fluoride ion is highlighted.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Sweis
Ramzi F
RF
D012821:Silanes / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
D012821:Silanes; D013451:Sulfonic Acids; C082343:silanol