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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

A simple link between hydrocarbon and borohydride chemistries.

Jordi Poater1, Miquel Solà, Clara Viñas

  • 1Institut de Química Computacional and Departament de Química, Universitat de Girona, Campus Montilivi, 17071 Girona, Catalonia, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 19, 2013
PubMed
Summary

Hydrocarbon and borohydride chemistries share a common root based on valence electrons. This finding enables the design of novel boron-containing molecules for synthetic chemistry applications.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Area of Science:

  • Chemistry
  • Computational Chemistry
  • Materials Science

Background:

  • Hydrocarbon and borohydride compounds are fundamental in chemistry.
  • Understanding the relationship between these classes can unlock new molecular designs.

Purpose of the Study:

  • To establish a clear link between hydrocarbon and borohydride chemistries.
  • To develop a predictive method for designing novel boron-containing molecules.

Main Methods:

  • Analysis of valence electron counts in confined spaces.
  • Application of a novel method to archetypal hydrocarbons.

Main Results:

  • A common root regulated by valence electrons was identified for hydrocarbons and borohydrides.
  • The method successfully predicted known borohydrides from hydrocarbons.
  • New boron-containing molecular structures were designed.

Conclusions:

  • The valence electron count is a unifying principle for hydrocarbon and borohydride chemistry.
  • The proposed method offers a powerful tool for discovering new boron compounds.
  • This research inspires synthetic chemists to explore novel boron-containing molecules.