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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.8K
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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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 stereochemistry.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
11.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.6K
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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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Oxidative-Insertion Reactivity Across a Geometrically Constrained Metal→Borane Interaction.

Brandon R Barnett1, Michael L Neville1, Curtis E Moore1

  • 1Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive MC 0358, La Jolla, CA, 92193, USA.

Angewandte Chemie (International Ed. in English)
|May 12, 2017
PubMed
Summary

This study introduces a platinum complex that activates diverse unsaturated molecules via oxidative insertion. This metal-borane complex facilitates new reactions, expanding synthetic chemistry possibilities.

Keywords:
boranescooperative effectsinsertionplatinumstructure elucidation

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Cooperative reactivity of transition metals and Lewis acids is an area of significant research interest.
  • The scope of known reactions involving the polarized reverse-dative σ-bond (M→BR3) in metal-borane complexes is limited.
  • Exploiting this unique bond is key to developing novel catalytic transformations.

Purpose of the Study:

  • To explore the reactivity of a platinum (boryl)iminomethane (BIM) complex.
  • To demonstrate the utility of the M→BR3 bond in oxidative insertion reactions.
  • To develop new synthetic methodologies utilizing metal-borane complexes.

Main Methods:

  • Synthesis and characterization of the platinum (boryl)iminomethane (BIM) complex [Pt(κ2 -N,B-Cy2 BIM)(CNArDipp2 )].
  • Investigation of the complex's reactivity with various unsaturated organic substrates, including azides, isocyanates, nitriles, CO2, and elemental sulfur (S8).
  • Analysis of reaction mechanisms, including oxidative insertion and alkyl migration processes.

Main Results:

  • The platinum-BIM complex successfully effected oxidative insertion of azides, isocyanates, nitriles, CO2, and S8.
  • Alkyl migration within the BIM framework enabled subsequent product release from the metal center.
  • This demonstrates a versatile reactivity profile for the platinum-borane system.

Conclusions:

  • The platinum-BIM complex serves as an effective platform for oxidative insertion reactions, broadening the utility of metal-borane chemistry.
  • The developed methodology offers new pathways for synthesizing diverse organometallic compounds.
  • This work expands the scope of reactions involving polarized reverse-dative σ-bonds in catalysis.