Novel Applications
of Polyfunctionalised Organoboron
and Nitroso Compounds

Abstract

This thesis deals with the reactivity of dienylboronated compounds towards aryl- and carbonylnitroso derivatives. The first part of this focused on the reactivity of dienylboronate compounds with arylnitroso derivatives resulting in pyrrole or furan formation. The outcome and efficiency of the reaction is related to the boron substituents and the solvent used, thus giving pyrroles, boronated oxazines or nitrones. A one-pot strategy was then applied to synthesise oxazoline derivatives using nitrones as key intermediates. Theoretical, as well as experimental, works supported that the formation of the pyrrole via regioselective nitroso Diels-Alder reaction/rearrangement/borate elimination cascade process. Secondly, attention was focused on the reactivity of dienylboronate compounds with carbonylnitroso derivatives. The nature of the carbonylnitroso had a dramatic impact on reactivity and, for example, the product resulting from a nitroso-ene reaction was obtained with pinacol derivatives. This ene-species was further used as the key intermediate for the synthesis of different polycyclic compounds. Several one-pot multicomponent processes were developed, giving access to various heterocycles with a high functional and structural diversity.