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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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Acid-Catalyzed Ring-Opening of Epoxides02:24

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.1K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Base-Catalyzed Ring-Opening of Epoxides02:26

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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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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Difuncionalización asimétrica catalizada por iridio de los enlaces C-C σ habilitados por complejos de boronato de

Hong-Cheng Shen1, Mihai V Popescu2, Ze-Shu Wang1

  • 1School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.

Journal of the American Chemical Society
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Resumen

Este estudio introduce un método catalizado por iridio para la difuncionalización asimétrica de enlaces C-C utilizando complejos de boronato de biciclo [1.1.0] butilo (BCB). La nueva reacción produce ciclobutanos enriquecidos con enantio con una diastereoselectividad única contra la adición.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Los compuestos de organoboron son intermediarios cruciales en la síntesis orgánica y el descubrimiento de fármacos.
  • Las reorganizaciones enantioselectivas de 1,2-metalato de los alquenilboronatos ofrecen una ruta a valiosos reactivos quirales.
  • La difuncionalización asimétrica de los enlaces C-C sigue siendo un desafío significativo en la química sintética.

Objetivo del estudio:

  • Desarrollar un nuevo alilado asimétrico catalizado por iridio inducido por el reordenamiento de 1,2-metalato de complejos de boronato de biciclo [1.1.0] butilo (BCB).
  • Para lograr la difuncionalización asimétrica de los enlaces C-C sigma, incluida la descarbonización y la carbonización.
  • Para sintetizar productos tridimensionales de ciclobutanos 1,1,3-trisubstituidos enriquecidos con enantio.

Principales métodos:

  • Reorganización inducida por alilación asimétrica catalizada por iridio de 1,2-metalato.
  • Utilizando la liberación de tensión en los complejos de biciclo[1.1.0]butil (BCB) boronato.
  • Empleando datos experimentales y cálculos de la teoría funcional de la densidad (DFT) para conocimientos mecanicistas.

Principales resultados:

  • Difuncionalización asimétrica exitosa de los enlaces C-C sigma.
  • Acceso a una variedad de productos de ciclo butano 1,1,3-trisubstituidos enriquecidos con enantio que contienen un éster de boro.
  • Observación de diastereoisómeros *trans* exclusivos resultantes de la *anti*-adición, en contraste con las vías de *sin*-adición anteriores.

Conclusiones:

  • El protocolo desarrollado proporciona un método novedoso y eficiente para sintetizar estructuras quirales complejas de ciclobutano.
  • La diastereoselectividad *anti*-adición observada se atribuye a la alta nucleofilicidad de los complejos de boronato BCB y los estados de transición temprana.
  • Este trabajo amplía el alcance de la difuncionalización asimétrica y ofrece bloques de construcción valiosos para futuras aplicaciones sintéticas.