Dihydroboration of 1-phenylselenyl-1-alkynes with dichloroborane-dioxane complex

ORGN 544

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Venessa Garate, 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 with n-butyllithium followed by reaction with phenylselenyl chloride, readily undergo dihydroboration with dichloroborane-dioxane complex in dichloromethane at room temperature for 12 h. The resulting dihydroborated products are reacted with water at 0 oC for 0.5 h followed by reaction with 1,3-propane diol in n-pentane. The corresponding dihydroborated products are isolated in good yields (72%-84%) and the structures of these intermediates are confirmed by spectral (PMR and CMR) data.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007