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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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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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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Catalytic intermolecular alkene oxyamination with nitrenes.

Geoffroy Dequirez1, Jennifer Ciesielski, Pascal Retailleau

  • 1Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette (France).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 19, 2014
PubMed
Summary
This summary is machine-generated.

Rh(II) catalysts enable efficient 1,2-oxyamination of alkenes with nitrenes, yielding vicinal amino alcohols. This reaction proceeds via an aziridine intermediate, offering high yields and regioselectivity.

Keywords:
alkenesaminohydroxylationnitrenesrhodiumsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Vicinal amino alcohols are crucial structural motifs in pharmaceuticals and natural products.
  • Efficient and selective methods for synthesizing vicinal amino alcohols remain a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a novel Rh(II)-catalyzed intermolecular 1,2-oxyamination reaction.
  • To achieve high yields and complete regioselectivity in the synthesis of vicinal amino alcohols.

Main Methods:

  • Utilized Rh(II) catalysts for the intermolecular addition of nitrenes to aromatic and aliphatic alkenes.
  • Investigated the reaction mechanism involving aziridine intermediate formation and subsequent ring-opening.

Main Results:

  • Achieved synthesis of vicinal amino alcohols with yields up to 95%.
  • Demonstrated complete regioselectivity in the 1,2-oxyamination reaction.
  • Identified the Rh-bound nitrene acting as a Lewis acid to induce aziridine ring opening.

Conclusions:

  • The developed Rh(II)-catalyzed reaction provides a highly efficient and regioselective route to vicinal amino alcohols.
  • The mechanistic insights reveal the role of the nitrene intermediate in driving the reaction pathway.