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Videos de Conceptos Relacionados

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
17.9K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Desbloquear la ambifilicidad del anión borilo: síntesis y reactividad de un diazoborano aniónico

Chonghe Zhang1, Junyi Wang2, Xibao Zhang1

  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|June 10, 2025
PubMed
Resumen

Los aniones borilo sustituidos por arilo exhiben ambifilicidad, reaccionando con varias moléculas como el monóxido de carbono y el óxido nitroso. Este estudio explora su doble comportamiento nucleófilo y electrófilo, revelando nuevas transformaciones químicas.

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Área de la Ciencia:

  • Química del organoboron
  • Química de los elementos del grupo principal
  • Química sintética inorgánica

Sus antecedentes:

  • Los aniones de boro (R2B-) suelen mostrar nucleofilicidad debido a la conjugación n-p.
  • Los aniones de boro sustituidos por arilo (Ar2B-) no se han estudiado ampliamente para las propiedades ambifílicas.

Objetivo del estudio:

  • Para sintetizar y caracterizar un nuevo anión borilo sustituido por arilo.
  • Para investigar el comportamiento ambifílico (dual nucleófilo/electrófilo) de este anión borilo.
  • Explorar nuevas vías de reacción y mecanismos que involucren a los aniones de boro.

Principales métodos:

  • Reacción de diazotización utilizando la hidrazina de Carpino para la síntesis.
  • Reacciones de intercambio de ligandos con el CO y los isocyanuros.
  • Reacciones con N2O y CO2.
  • Análisis de la Teoría Funcional de Densidad (DFT) para conocimientos mecanicistas.

Principales resultados:

  • Síntesis del anión diazoborano [K(2.2.2-criptand) ]+Dmp(Mes) BN2- (3).
  • El compuesto 3 actúa como una fuente libre de aniones borilo y exhibe reactividad ambifílica.
  • Formación de oxoborano y productos de cicloadición con N2O y CO2, respectivamente.
  • Observación de la liberación de N2 y posterior activación del enlace en condiciones térmicas o fotolíticas.

Conclusiones:

  • Los aniones de boro sustituidos por arilo pueden exhibir ambifilicidad, desafiando los puntos de vista tradicionales.
  • El compuesto 3 sirve como un precursor versátil para nuevos compuestos de organoboron.
  • Los estudios de DFT proporcionan una comprensión mecánica crucial de estas reacciones únicas.