New Carbon-Carbon Bond Forming Reactions Mediated by Boron and Transition Metal Halides

Author

Travis R. Quick, University of Tennessee - Knoxville

Date of Award

12-2008

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

Shane Foister, Bin Zhao, Engin Serpersu

Abstract

This dissertation summarizes the recent use of boron and transition metal halides to form new carbon-carbon bonds. Several novel reactions have been discovered. These include the haloallylation of aryl aldehydes with boron trihalide; alkyne-aldehyde couplings mediated by boron trihalide to give either (Z,Z)-1,5-dihaloalkenes or (Z,E)-1,5- dihaloalkenes; dehydroxylation of benzylic alcohols and in situ generated benzylic alcohol salts with iron(III) chloride and triethylsilane to afford diarylmethanes; and, the alkenylation of allylic, benzylic, and propargylic alcohols with phenylacetylenes and titanium(IV) halide. The results of these studies strongly imply a cationic mechanism. The reaction methodology of the research described herein can be characterized as atomefficient, environmentally friendly, and capable of generating the desired products in good to excellent yields.

Recommended Citation

Quick, Travis R., "New Carbon-Carbon Bond Forming Reactions Mediated by Boron and Transition Metal Halides. " PhD diss., University of Tennessee, 2008.
https://trace.tennessee.edu/utk_graddiss/593