Le diisopropylaminoborane : un agent de borylation alternatif pour la pformation de liaison carbone-bore. Etude de réactivité et développement de nouvelles méthodologies.

摘要

This manuscript describes the use of diisopropylaminoborane as borylating agent of aryl halides anddiazonium salts. This borylating agent has been the subject of studies in the laboratory and newmethodologies has been done. A general methodology of borylation of aryl diazonium salt catalyzed byiron, titanium and zirconium metallocene was developed, allowing access to useful compounds such ashalogenated aryl boron species. Furthermore, kinetic and mechanistic studies supported by theoreticalcalculation allowed a better understanding of the mechanism of the reaction. An extension of thepalladium catalyzed reaction was realized, allowing the use of aryl bromides and chlorides together witha new one-pot unsymetrical biaryl synthesis. Those methods allowed an efficient borylation of arylshalides using homogeneous semi-heterogeneous palladium catalyst. Finally, a study of reactivity of thediisopropylaminoborane and organometallics such as Grignard and organolithium was done. A generalmethodology was developed for the synthesis of diarylborinic acids and a mechanistic study wasachieved.