Publication: Nuevas reacciones estereoselectivas de formación de enlaces C-C empleando ácidos borónicos en ausencia de metal de transición
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2020-03-19
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Universidad Complutense de Madrid
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Abstract
El desarrollo de nuevos métodos de formación de enlaces C-C es fundamental para la síntesis de nuevos compuestos orgánicos. En este sentido, los ácidos borónicos y sus derivados los organotrifluoroboratos potásicos constituyen una opción interesante, ya que, al contrario que otros nucleófilos carbonados como son los magnesianos o los cupratos, son compuestos estables, compatibles con una gran variedad de grupos funcionales, presentan baja toxicidad y muchos de ellos se encuentran comercialmente disponibles. A pesar de estas ventajas, los ácidos borónicos poseen una nucleofilia moderada, siendo necesario algún tipo de activación adicional en los procedimientos sintéticos en los que se ven involucrados. Concretamente, las reacciones más populares de formación de enlaces C-C empleando ácidos borónicos requieren del empleo de metales de transición. Comparativamente, las transformaciones en ausencia de dichos metales han sido mucho menos exploradas. El descubrimiento de nuevas metodologías que permitan la formación estereoselectiva de enlaces C-C empleando ácidos borónicos en ausencia de metal de transición constituye una aportación importante a la química de estos compuestos...
Investigation of new methods for the construction of C–C bonds is fundamental for the development of new organic compounds. Boronic acids and their derivatives constitute attractive reagents towards this end. Opposite to other conventional organometallic carbon nucleophiles, such as organolithiums, Grignard reagents or cuprates, these compounds are thermally stable and compatible with a large variety of functional groups. In addition, a large number of them are nowadays commercially available or can be prepared by easy synthetic routes, and their toxicity is low. Despite these advantages, boronic acids and their derivatives are only moderately nucleophilic. This requires the inclusion of some type of extra activation in the synthetic procedures. Most frequently, transition metal catalysis has been used towards this end. Comparatively, synthetic transformations under metal-free conditions have been much less explored. The finding of new reactions that enable C-C bond formation using boronic acids under metal-free conditions is a highly attractive addendum to the synthetic arsenal of these compounds...
Investigation of new methods for the construction of C–C bonds is fundamental for the development of new organic compounds. Boronic acids and their derivatives constitute attractive reagents towards this end. Opposite to other conventional organometallic carbon nucleophiles, such as organolithiums, Grignard reagents or cuprates, these compounds are thermally stable and compatible with a large variety of functional groups. In addition, a large number of them are nowadays commercially available or can be prepared by easy synthetic routes, and their toxicity is low. Despite these advantages, boronic acids and their derivatives are only moderately nucleophilic. This requires the inclusion of some type of extra activation in the synthetic procedures. Most frequently, transition metal catalysis has been used towards this end. Comparatively, synthetic transformations under metal-free conditions have been much less explored. The finding of new reactions that enable C-C bond formation using boronic acids under metal-free conditions is a highly attractive addendum to the synthetic arsenal of these compounds...
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Tesis inédita de la Universidad Complutense de Madrid, Facultad de Ciencias Químicas, Departamento de Química Orgánica I, leída el 08/11/2019