Facile dihydroboration of 1-trimethylsilyl-1-alkynes with 9-borabicyclo[3.3.1]nonane(9-BBN) followed by oxidation

ORGN 565

Narayan G. Bhat, nbhat@panam.edu1, Robert L. Salazar2, and Aroldo J. Ibarra2. (1) Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, (2) Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541
1-Trimethylsilyl-1-alkynes easily prepared by the deprotonation of the terminal alkynes with n-butyllithium followed by reaction with trimethylchlorosilane readily undergo dihydroboration with 9-borabicyclo[3.3.1]nonane (9-BBN) in tetrahydrofuran at room temperature for 12 h. The resulting dihydroborated products are reacted with alkaline hydrogen peroxide at 0 oC followed by stirring at room temperature for 4 hours to provide the corresponding alpha-trimethylsilyl-1-alkanols in excellent yields (80%-88%). The structures of these alpha-trimethylsilyl-1-alkanols are confirmed by NMR spectral data.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006