New synthetic routes towards 1,4- dienylboronates via catalytic alkyne allylboration reactions
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 synthes...
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| Formato: | tesis doctoral |
| Fecha de publicación: | 2022 |
| País: | España |
| Recursos: | Universidad de Santiago de Compostela (USC) |
| Repositorio: | Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela |
| Idioma: | inglés |
| OAI Identifier: | oai:minerva.usc.gal:10347/27566 |
| Acesso em linha: | http://hdl.handle.net/10347/27566 |
| Access Level: | acceso abierto |
| Palavra-chave: | Materias::Investigación::22 Física::2210 Química física::221001 Catálisis Materias::Investigación::23 Química::2303 Química inorgánica::230304 Compuestos de boro Materias::Investigación::23 Química::2303 Química inorgánica::230316 Mecanismos de las reacciones inorgánicas |
| Resumo: | 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. |
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