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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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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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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Halogenation of Alkenes02:46

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Recent advances in borenium catalysis.

Xinyue Tan1, Huadong Wang1

  • 1Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Songhu Road 2005, Shanghai, 200438, P. R. China. huadongwang@fudan.edu.cn.

Chemical Society Reviews
|March 9, 2022
PubMed
Summary
This summary is machine-generated.

Borenium ions, potent Lewis acids, are now effective catalysts in organic synthesis thanks to supporting ligands. They enable the activation of strong covalent bonds, advancing catalytic applications.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Borenium ions are strong Lewis acids due to their positive charge.
  • Historically, their high reactivity limited them to stoichiometric roles in synthesis.

Purpose of the Study:

  • To review recent advancements in borenium-catalyzed reactions.
  • To highlight catalyst synthesis, methodology, and mechanistic understanding.

Main Methods:

  • Review of literature on borenium ion catalysis.
  • Focus on reactions involving N-heterocyclic carbene ligands.
  • Analysis of bond activation mechanisms (H-H, Si-H, B-H, C-H, C-C).

Main Results:

  • N-heterocyclic carbenes enable borenium ions to act as catalysts.
  • Successful activation of various strong covalent bonds.
  • Development of new synthetic methodologies using borenium catalysts.

Conclusions:

  • Borenium ions are versatile catalysts for organic transformations.
  • Ligand design is key to controlling borenium reactivity.
  • Continued research promises further applications in catalysis.