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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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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.4K
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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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.2K
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...
3.2K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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A deprotonation pathway to reactive [B]CH2 boraalkenes.

Karel Škoch1, Chaohuang Chen1, Constantin G Daniliuc1

  • 1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany. erker@uni-muenster.de.

Dalton Transactions (Cambridge, England : 2003)
|May 6, 2022
PubMed
Summary

New boraalkenes were synthesized and reacted with sulfur, carbon dioxide, and sulfur dioxide to form novel boron-containing heterocycles. These compounds also reacted with Lewis acidic boranes and gold complexes.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Area of Science:

  • Organoboron Chemistry
  • Synthetic Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Boron-containing compounds, particularly boraalkenes, are valuable synthetic intermediates.
  • Understanding the reactivity of boraalkenes is crucial for developing new synthetic methodologies.
  • Previous studies have explored the cycloaddition and Lewis acid-mediated reactions of boron compounds.

Purpose of the Study:

  • To synthesize novel boraalkenes with specific aryl substituents (ArF: C6F5 or FpXyl).
  • To investigate the reactivity of these boraalkenes with various reagents, including elemental sulfur, carbon dioxide, sulfur dioxide, Lewis acidic boranes, and gold complexes.
  • To explore the formation of new boron-containing heterocycles and organometallic complexes.

Main Methods:

  • A three-step reaction sequence involving B-methylation, hydride abstraction, and deprotonation was employed to synthesize the boraalkenes.
  • Reactions of the synthesized boraalkenes with elemental sulfur, carbon dioxide, and sulfur dioxide were performed to study cycloaddition reactions.
  • The addition of Lewis acidic boranes (e.g., HB(C6F5)2) and reaction with [(Me2S)AuCl] were conducted to explore complex formation.

Main Results:

  • The synthesized IMes(ArF)B=CH2 boraalkenes successfully reacted with elemental sulfur to yield thiaborirane products.
  • [2+2] cycloaddition reactions with CO2 and SO2 resulted in the formation of four-membered boron-containing heterocycles.
  • Boraalkenes readily added Lewis acidic boranes at the exocyclic methylene carbon, leading to adducts that could reduce carbon monoxide.
  • Complexation with [(Me2S)AuCl] yielded the corresponding (boraalkene)AuCl complexes.

Conclusions:

  • The developed synthetic route provides access to a range of functionalized boraalkenes.
  • These boraalkenes exhibit versatile reactivity, participating in cycloaddition, Lewis acid-mediated reactions, and organometallic complexation.
  • The study highlights the potential of boraalkenes as building blocks for novel heterocyclic compounds and organometallic chemistry.