Date of Award

5-2005

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

Richard M. Pagni, Ziling (Ben) Xue, Engin Serpersu

Abstract

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.

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