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Related Concept Videos

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

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

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.6K
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.
9.6K
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

3.1K
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

8.0K
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...
8.0K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

10.2K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Related Experiment Video

Updated: Mar 8, 2026

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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Formose reaction controlled by boronic acid compounds.

Toru Imai1, Tomohiro Michitaka1, Akihito Hashidzume1

  • 1Department of Macromolecular Science, Graduate School of Science, Osaka University, 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan.

Beilstein Journal of Organic Chemistry
|February 2, 2017
PubMed
Summary

Formose reactions using boronic acid compounds yielded different sugar products. Sodium phenylboronate (SPB) favored smaller sugars, while a copolymer (pVPB/NaSS) produced larger sugar alcohols.

Keywords:
boronic acid compoundsformose reactionsodium 4-vinylphenylboronate/sodium 4-styrenesulfonate copolymersodium phenylboronatesugar alcoholssugars

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Area of Science:

  • Carbohydrate chemistry
  • Polymer chemistry
  • Organic synthesis

Background:

  • The Formose reaction is a key process in prebiotic chemistry for synthesizing sugars from formaldehyde.
  • Controlling the selectivity of the Formose reaction is crucial for understanding sugar formation pathways.
  • Boronic acid compounds are known to interact with diols, potentially influencing carbohydrate synthesis.

Purpose of the Study:

  • To investigate the effect of low molecular weight and macromolecular boronic acid compounds on Formose reaction selectivity.
  • To determine if different boronic acid structures can direct the formation of specific carbohydrate products.
  • To explore the potential of tailored boronic acid catalysts in carbohydrate synthesis.

Main Methods:

  • Carrying out Formose reactions in the presence of sodium phenylboronate (SPB) and a copolymer of sodium 4-vinylphenylboronate with sodium 4-styrenesulfonate (pVPB/NaSS).
  • Analyzing the product distribution of the Formose reaction under different catalytic conditions.
  • Characterizing the synthesized sugars and sugar alcohols.

Main Results:

  • Sodium phenylboronate (SPB) selectively promoted the formation of sugars with a smaller carbon number.
  • The macromolecular boronic acid compound, pVPB/NaSS, preferentially yielded sugar alcohols with a larger carbon number.
  • The molecular weight and structure of the boronic acid compound significantly influenced the reaction's selectivity.

Conclusions:

  • Boronic acid compounds can effectively modulate the selectivity of the Formose reaction.
  • Low molecular weight boronic acids favor smaller carbohydrates, whereas macromolecular variants promote larger sugar alcohols.
  • This study highlights the potential of using designed boronic acid catalysts for targeted carbohydrate synthesis.