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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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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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 stereochemistry.
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Hydroboration-Oxidation of Alkenes03:08

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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: Acid-Catalyzed Hydration02:40

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Hidroboración geminal catalizada por Ru de alquinas de silicio mediante un nuevo mecanismo de adición de gemas

Qiang Feng1, Haonan Wu2,3, Xin Li2

  • 1Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, SAR, China.

Journal of the American Chemical Society
|July 16, 2020
PubMed
Resumen

Este estudio introduce una nueva hidroboración de 1,1-alquinas, logrando la adición de geminal (H,B). Esta nueva vía, catalizada por un complejo de rutenio, sintetiza eficientemente valiosos boronatos de vinilo silílico.

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Área de la Ciencia:

  • Química organometálica
  • Química orgánica sintética

Sus antecedentes:

  • La adición de 1,2 es la vía de hidroboración predominante para los alquinos.
  • Se necesita un nuevo modo de hidroboración regioselectiva para expandir la utilidad sintética.

Objetivo del estudio:

  • Para informar el primer ejemplo de 1,1-hidroboración de alquinas.
  • Desarrollar un sistema catalítico para la adición de geminales (H,B) a las alquinas.
  • Para aclarar el mecanismo de esta nueva transformación.

Principales métodos:

  • La catálisis se realiza con [CpRu(MeCN) 3PF6.
  • Reacción de las alquinas silílicas con HBpin en condiciones leves.
  • Estudios mecanicistas, incluidos los experimentos de control y los cálculos del DFT.

Principales resultados:

  • Síntesis eficiente de los boronatos de silil-vinilo mediante la hidroboración del 1,1.
  • Se observó una estereoselectividad completa y una amplia tolerancia del grupo funcional.
  • Demostración de la extensión a las alquinas germanilas y las reacciones de hidrosilación relacionadas.
  • Identificación de un nuevo mecanismo que implica una adición de geminal (H,B) y un intermediario de Ru-carbeno, excluidos los intermediarios de vinilideno.

Conclusiones:

  • Se ha establecido una nueva hidroboración de 1,1-alquinas, que permite la adición de geminal (H,B).
  • El método desarrollado catalizado por rutenio proporciona acceso a boronatos de vinilo silílico sintéticamente útiles.
  • Las ideas mecanicistas avanzan en la comprensión de la funcionalización de alquinos y las reacciones de adición geminales.