Development of Novel Synthetic Methods Utilizing Group III and IV Reagents

This dissertation summarizes the development of novel synthetic methods involving Group III & IV reagents. These newly discovered reactions include the rhodium-catalyzed direct cross-coupling of allylic alcohols with aryl- and vinylboronic acids; palladium-catalyzed coupling reaction of Baylis-Hillman acetate adducts with both potassium organotrifluoroborate reagents and organosiloxanes; efficient syntheses of functionalized allylmetals such as allylboranes, allylsilanes, and allylgermanes; application of allylboranes to the synthesis of homoallylic alcohols; syntheses of 4-(1-alkynyl)-2(5H)-furanones and coumarins; utilization of potassium alkynyltrifluoroborates in the synthesis of conjugated enediynes; and application of potassium alkynyltrifluoroborates as reagents in the Petasis reaction.

The new synthetic methodologies involving Group III & IV reagents developed in this dissertation are important transformations in modern organic synthesis. Mild reaction conditions and a tolerance for various organic functional groups are advantages of these methodologies. The ability to recycle the catalytic system in some cases is another attractive feature for ionic liquids-involved methods.