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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.6K
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.
10.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.3K
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.
20.3K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.2K
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.
9.2K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.8K
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.
8.8K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.1K
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...
7.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.7K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.7K

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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

Published on: November 30, 2022

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Boracene-based alkylborate enabled Ni/Ir hybrid catalysis.

Yukiya Sato1, Yusuke Miyamoto, Yuto Sumida

  • 1Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kanazawa 920-1192, Japan. sumida@p.kanazawa-u.ac.jp ohmiya@p.kanazawa-u.ac.jp.

Organic & Biomolecular Chemistry
|August 20, 2020
PubMed
Summary

Boracene-based alkylborates enable visible light catalysis. This Ni/Ir hybrid system achieves efficient product formation using low light intensity, advancing metallaphotoredox catalysis.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
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Area of Science:

  • Organometallic Chemistry
  • Photocatalysis
  • Sustainable Chemistry

Background:

  • Visible light photocatalysis offers a sustainable alternative to traditional synthetic methods.
  • Metallaphotoredox catalysis combines the advantages of metal catalysis and photoredox catalysis.
  • Boron-based compounds are emerging as versatile components in catalytic systems.

Purpose of the Study:

  • To develop a novel boracene-based alkylborate for visible light-mediated metallaphotoredox catalysis.
  • To investigate the catalytic activity of a Ni/Ir hybrid system utilizing the borate.
  • To achieve efficient product formation under low light irradiance.

Main Methods:

  • Visible light irradiation of a reaction mixture containing boracene-based alkylborate and a Ni/Ir catalyst.
  • Oxidative quenching of the excited borate by an excited iridium photoredox catalyst.
  • Analysis of reaction products to determine catalytic efficiency.

Main Results:

  • Boracene-based alkylborate successfully mediated visible light photocatalysis.
  • The excited borate underwent efficient oxidative quenching by the excited Ir catalyst.
  • The Ni/Ir hybrid catalysis system demonstrated high efficiency under significantly low light irradiance, affording desired products.

Conclusions:

  • Boracene-based alkylborates are effective mediators in visible light metallaphotoredox catalysis.
  • The Ni/Ir hybrid system provides a highly efficient catalytic pathway under mild conditions.
  • This approach offers a promising route for sustainable organic synthesis using low light energy.