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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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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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The large ribosomal subunit has several important structures essential to translation. These include the peptidyl transferase center (PTC) - which is the site where the peptide bond is formed - and a large, internal, water-filled tube through which the nascent polypeptide moves. This latter structure is called the Peptide Exit Tunnel, and it begins at the PTC and spans the body of the large ribosomal subunit. During translation, as the nascent polypeptide chain is synthesized, it passes through...
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Herein, detailed protocols for the oxidative iodination of terminal alkynes using hypervalent-iodine reagents are presented, which chemoselectively afford 1-iodoalkynes, 1,2-diiodoalkenes, and...
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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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Microwave-assisted intramolecular dehydrogenative Diels-Alder (DA) reactions provide concise access to functionalized cyclopenta[b]naphthalene building blocks. The utility of this methodology is demonstrated by one-step conversion of the dehydrogenative DA cycloadducts into novel solvatochromic fluorescent dyes via Buchwald-Hartwig palladium-catalyzed cross-coupling...
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Updated: Jan 19, 2026

Hydroboration-Oxidation of Alkynes to Aldehydes and Ketones
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Catalizado por rutenio (Z) - Hidroboración selectiva de las alquinas terminales con naftaleno-1,8-diaminatoborano

Kensuke Yamamoto1, Yusei Mohara1, Yuichiro Mutoh1

  • 1Department of Chemistry, Faculty of Science , Tokyo University of Science , 1-3 Kagurazaka, Shinjuku-ku , Tokyo 162-8601 , Japan.

Journal of the American Chemical Society
|September 17, 2019
PubMed
Resumen

Los complejos de rutenio catalizan la desafiante hidroboración Z-selectiva de las alquinas terminales utilizando H-B (dan). Esto genera valiosos Z-alquenilboranos, lo que permite una rápida síntesis de los análogos de Combretastatina A-4.

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Área de la Ciencia:

  • Química organometálica
  • Catálisis
  • Química orgánica sintética

Sus antecedentes:

  • La hidroboración catalizada por metales de los alquinos generalmente produce isómeros E.
  • El isómero Z es termodinámicamente inestable, lo que dificulta su síntesis selectiva.

Objetivo del estudio:

  • Desarrollar un sistema catalítico para la hidroboración Z-selectiva de las alquinas terminales.
  • Para sintetizar los valiosos Z-alquenilboranos.
  • Explorar aplicaciones en la síntesis de compuestos biológicamente activos.

Principales métodos:

  • Se utilizan complejos de rutenio ligados a N-heterocíclicos y carbenos.
  • Se utiliza H-B (dan) (dan = naftaleno-1,8-diaminato) como fuente de boro.
  • Se han realizado estudios mecanicistas, incluido el aislamiento de un intermediario de borilrutenio.

Principales resultados:

  • Se ha logrado una alta selectividad Z en la hidroboración de alquinas terminales.
  • Generó una amplia gama de Z-alquenilboranos sintéticamente útiles.
  • Demostró la utilidad del Z-alquenil-B (dan) en las reacciones de acoplamiento cruzado.

Conclusiones:

  • La reacción catalizada por rutenio desarrollada proporciona un acceso eficiente a los alquenilboranos Z.
  • Se aclaró un nuevo ciclo catalítico que implica la inserción de alquina en un enlace Ru-B.
  • Esta metodología facilita la síntesis rápida de los análogos de Combretastatina A-4.