Video Experimental Relacionado

Updated: Nov 5, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Meta-borilación selectiva de C-H de sustratos estéricamente sesgados y no sesgados dirigida por la interacción

Jagriti Chaturvedi^1,2, Chabush Haldar¹, Ranjana Bisht¹

¹Division of Molecular Synthesis & Drug Discovery, Center of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow 226014, Uttar Pradesh, India.

Journal of the American Chemical Society

|May 14, 2021

Resumen

Este estudio introduce un nuevo método de metaborilación que utiliza interacciones electrostáticas para la borilación selectiva de sustratos difíciles. El enfoque evita ligandos complejos y condiciones difíciles, lo que permite una metafuncionalización eficiente.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La funcionalización selectiva de las moléculas orgánicas es crucial en la síntesis.
La meta-borilación de compuestos aromáticos sigue siendo un desafío sintético, especialmente para los sustratos estéricamente obstaculizados.

Objetivo del estudio:

Desarrollar una nueva estrategia de metaborilación dirigida electrostáticamente.
Para lograr la meta-borilación selectiva de sustratos diversos y difíciles, incluidos los aromáticos 4-sustituidos y no sustituidos.

Principales métodos:

Utilizando una interacción electrostática entre un ligando y un sustrato para dirigir la borilación.
Empleando un ligando estable en el banco y condiciones de reacción más suaves.

Principales resultados:

Se ha demostrado la meta-borilación selectiva de sustratos estéricamente sesgados y no sesgados.
Se ha logrado una excelente meta selectividad para compuestos aromáticos 4-sustituidos y no sustituidos.
La reacción procede de manera eficiente sin la necesidad de ligandos o plantillas complejas.

Conclusiones:

La meta borilación dirigida electrostáticamente ofrece un método poderoso y general para la funcionalización aromática selectiva.
Esta estrategia simplifica las rutas sintéticas al evitar la síntesis elaborada de ligandos y las condiciones adversas.

Más Videos Relacionados

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Videos de Conceptos Relacionados

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Directing and Steric Effects in Disubstituted Benzene Derivatives

Directing and Steric Effects in Disubstituted Benzene Derivatives

When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...