Novel route to (Z)-1-phenylselenyl-1-alkenylboronate esters via hydroboration

ORGN 133

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Robert K. Ruiz, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
1-Phenylselenyl-1-alkynes easily prepared by the deprotonation of the corresponding terminal alkynes followed by treatment with phenylselenyl chloride, readily react with dichloroborane-dioxane complex in dichloromethane at room temperature for 12 h. The resulting solution is then treated with 1,3-propane diol at 0 oC for half an hour to provide the corresponding (Z)-1-phenylselenyl-1-alkenylboronate esters in high yields (72%-83%) and the oxidation studies of these intermediates are currently in progress.