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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.3K
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.
21.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.7K
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.
9.7K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

8.2K
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...
8.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.5K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Related Experiment Video

Updated: Mar 31, 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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Metal-Free Hydrosilylation Polymerization by Borane Catalyst.

Dong Wook Kim1,2, Seewon Joung3,4, Jeung Gon Kim5,6,7

  • 1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141 (Korea).

Angewandte Chemie (International Ed. in English)
|October 17, 2015
PubMed
Summary

This study introduces metal-free hydrosilylation polymerization using a borane catalyst, enabling the synthesis of diverse polycarbosilanes under mild conditions. This approach offers a sustainable alternative to precious transition-metal catalysts for creating advanced polymer materials.

Keywords:
borane catalysthydrosilylationmetal-free catalysispolycarbosilanespolymerization

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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Last Updated: Mar 31, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Area of Science:

  • Polymer Chemistry
  • Organometallic Catalysis

Background:

  • Hydrosilylation polymerization typically relies on precious transition metals.
  • Developing metal-free alternatives is crucial for sustainable chemistry.

Purpose of the Study:

  • To develop the first metal-free hydrosilylation polymerization method.
  • To utilize readily available dienes and disilanes for polymer synthesis.

Main Methods:

  • Employed a borane catalyst, B(C6F5)3, for metal-free hydrosilylation.
  • Conducted step-growth polymerization under mild and easy-to-handle conditions.

Main Results:

  • Achieved high degrees of polymerization in the synthesized polymers.
  • Produced a diverse range of polycarbosilanes by varying diene and disilane combinations.
  • Demonstrated the efficacy of the borane catalyst in replacing transition metals.

Conclusions:

  • Established a novel, metal-free route for synthesizing polycarbosilanes.
  • The developed method offers a sustainable and versatile approach to polymer production.
  • The resulting polycarbosilanes exhibit tunable structures and properties.