Boron and Metal Halides in Organic Synthesis

This dissertation summarizes the recent use of organoboron and metal halides to form new carbon-carbon bonds. Several novel reactions have been discovered. These include the halovinyl alkenylation of alkoxides with alkenylboron dihalides; alkynylation of alkoxides with alkynylboron dihalides; boron trichloride and ferric chloride-mediated allylation of alkoxides. The results of these studies strongly imply a cationic mechanism, and prompted a reinvestigation of the boron trihalide mediated alkyne-aldehyde coupling reaction. The olefin stereochemistry of the resultant 1,5-dihalo-1,4-pentadienes can be influenced by controlling the reaction temperature and the sequence of reagent addition. 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 high yields.