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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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Oxidative Cleavage of Alkenes: Ozonolysis01:46

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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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.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxymercuration-Reduction of Alkenes02:36

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Catalizado por el oro, transferencia a los alcinos internos. Síntesis regioselectiva de los oxazoles

Karina O Mahmedova1, Vadim Yu Kukushkin1,2, Alexey Yu Dubovtsev1

  • 1Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.

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Una nueva reacción catalizada por oro crea eficientemente oxazoles trifluorometilados utilizando alquinas, N-óxidos de piridina y nitriles. El grupo trifluorometilo dirige la reacción, produciendo compuestos valiosos con alta eficiencia y tolerancia al grupo funcional.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Los N-óxidos de piridina son precursores versátiles en la síntesis orgánica.
  • Los heterociclos trifluorometilados son motivos importantes en la química medicinal y la ciencia de los materiales.
  • El desarrollo de métodos catalíticos regioselectivos para la construcción de moléculas complejas es un desafío clave.

Objetivo del estudio:

  • Desarrollar una nueva reacción de tres componentes catalizada por oro altamente regioselectiva.
  • Para sintetizar varios oxazoles 4-trifluorometilados.
  • Para aclarar el mecanismo, en particular el papel del grupo trifluorometilo.

Principales métodos:

  • Reacción de transferencia de oxígeno catalizada por el oro.
  • Se utilizan alquinas trifluorometiladas internas, N-óxidos de piridina y nitriles.
  • Estudios mecanicistas que incluyen la investigación del efecto directivo de la molécula CF3.

Principales resultados:

  • Desarrolló una reacción de transferencia de oxígeno única catalizada por oro altamente regioselectiva.
  • Se han sintetizado 30 ejemplos de oxazoles 4-trifluorometilados de alto rendimiento (hasta un 96%).
  • Se ha demostrado una tolerancia significativa del grupo funcional y condiciones de reacción leve.

Conclusiones:

  • El método desarrollado proporciona un acceso eficiente a valiosos oxazoles 4-trifluorometilados.
  • El grupo trifluorometilo juega un papel directivo crucial a través de un mecanismo inductivo.
  • La reacción ofrece potencial para la modificación fácil del grupo CF3 de dirección.