Organoboron halides in organic synthesis

This dissertation summarizes our recent researches in organoboron halides chemistry. The coordination of the very effective Lewis acids, boron halides or organoboron halides, with weak Lewis bases, carbonyl compounds mediated a series of new reactions. These newly-discovered reactions include reductive bromination of aromatic aldehydes to give rise to benzyl bromides; alkylation and chloroalkylation of aromatic aldehydes by alkylboron dichloride and dialkylboron chloride; dialkenylation of aldehydes to 1,3,5-triaryl-1,5-dihalo-l ,4-dienes with alkynes mediated by boron trihalides; addition of aldehydes with styrenes to form 1,3-diaryl-1,3-dihalo-propanes in the presence of boron halides, and reactions of aromatic aldehydes with styrenes and (E)J3- methylstyrene to afford 1,3-diaryl-3-chloro-1-propanaols stereo- and regioselectively. The new synthetic methodologies involving organoboron halides developed in this dissertation are important transformations in modem organic synthesis. Mild reaction conditions and tolerance of various organic functional groups are advantages of utilizing boron reagents in synthesis.