New synthetic routes towards 1,4- dienylboronates via catalytic alkyne allylboration reactions

Abstract

In this Ph.D. thesis, the synthesis of 1,4-dienyl boronates is explored using transition metal-catalyzed methodologies. In chapter I an introduction about the most important features of organoboron compounds and the most common methods to synthetize them is reported. Chapter II describes the synthesis of linear borylated 1,4-dienes through a synergistic Cu/Pd catalyzed stereo- and regioselective allylboration of alkynes. In chapter III, we explore the synthesis of multifunctional branched borylated 1,4-dienes by means of a copper-catalyzed stereo- and regioselective allylboration of alkynes. Then, we report the use of these 1,4-dienes for the synthesis of a new type of organoboron compounds, borylated dendralenes. In chapter IV, an enantioselective version of the allylboration of alkynes reported in chapter III with a chiral copper catalyst is disclosed. Finally, chapter V details the discovery of a novel transformation that entails á la carte multifunctionalization of borylated dendralenes to access to highly substituted 1,3-dienes.