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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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.
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Regioselectivity and Stereochemistry of Hydroboration02:36

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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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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

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The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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La reacción de acoplamiento cruzado de Suzuki-Miyaura promovida por trimetilsilanolato de potasio se produce a través

Connor P Delaney1, Daniel P Marron2, Alexander S Shved1

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|March 1, 2022
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Resumen

Las reacciones de acoplamiento cruzado Suzuki-Miyaura pueden ocurrir a través de una nueva vía de boronato, distinta de la ruta de oxo-palladio establecida. Este estudio identifica un complejo binuclear de paladio (I) sin precedentes potencialmente involucrado en este ciclo catalítico.

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Área de la Ciencia:

  • Química orgánica
  • Química organometálica
  • Catálisis

Sus antecedentes:

  • El acoplamiento Suzuki-Miyaura es una reacción vital en la síntesis orgánica.
  • El paso de transmisión generalmente procede a través de una vía de oxo-palladio que involucra ácidos borónicos de arilo.
  • La vía del boronato, utilizando boronatos de arilo, se ha considerado demasiado lenta para su aplicación práctica.

Objetivo del estudio:

  • Investigar el mecanismo de las reacciones de acoplamiento cruzado Suzuki-Miyaura promovidas por el trimetilsilanolato de potasio (TMSOK).
  • Explorar vías de reacción alternativas más allá del mecanismo de oxo-palladio establecido.
  • Caracterizar los nuevos complejos de paladio involucrados en el ciclo catalítico.

Principales métodos:

  • Aislamiento y caracterización de los intermedios de reacción.
  • Análisis cinético de las velocidades de reacción.
  • Espectroscopia de resonancia magnética nuclear (RMN), espectrometría de masas y métodos computacionales (DFT) para la caracterización compleja.

Principales resultados:

  • Demostración de que las reacciones de Suzuki-Miyaura promovidas por TMSOK proceden a través de la vía del boronato.
  • Descubrimiento y caracterización de un complejo binuclear sin precedentes de paladio con un ligando puente μ-fenilo.
  • Los cálculos de la teoría funcional de la densidad (DFT) indican un estado electrónico básico de cáscara abierta para el complejo binuclear.
  • La cinética de la reacción sugiere que el complejo binuclear participa en el ciclo catalítico.

Conclusiones:

  • El mecanismo de reacción de Suzuki-Miyaura es más diverso de lo que se entendía anteriormente, y la vía del boronato es viable en condiciones específicas.
  • El nuevo complejo binuclear de paladio representa un descubrimiento significativo con implicaciones potenciales para varias reacciones de acoplamiento cruzado catalizadas por paladio.
  • Esta investigación amplía el alcance mecanicista de los acoplamientos Suzuki-Miyaura y destaca nuevas vías en la catálisis del paladio.