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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.1K
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.
12.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.8K
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.
21.8K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

14.8K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
14.8K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

6.4K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
6.4K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.4K
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.
9.4K
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

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Updated: Mar 26, 2026

A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
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A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments

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Alkane biohydroxylation: Interests, constraints and future developments.

Laurence Soussan1, Nakry Pen1, Marie-Pierre Belleville1

  • 1IEM (European Institute of Membranes), UMR 5635 (CNRS-ENSCM-Montpellier University), Place E. Bataillon, F-34095 Montpellier, France.

Journal of Biotechnology
|February 9, 2016
PubMed
Summary

This study reviews recent advances in alkane biohydroxylation, converting alkanes into alcohols using enzymes or whole cells. It also discusses scaling up these bioconversions in bioreactors for fine chemical production.

Keywords:
Alcohol removalAlkanesBiocatalystsBiohydroxylationBioreactorsCofactor regeneration

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Experimental Protocol for Biodiesel Production with Isolation of Alkenones as Coproducts from Commercial Isochrysis Algal Biomass
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Area of Science:

  • Biotechnology
  • Organic Chemistry
  • Chemical Engineering

Background:

  • Alkanes are abundant raw materials for producing valuable fine chemicals.
  • Direct functionalization of alkanes remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To review recent advancements in alkane biohydroxylation.
  • To discuss the application of enzyme and whole-cell biocatalysts for alkane activation.
  • To explore process considerations for large-scale bioreactor implementation.

Main Methods:

  • Literature review of enzyme and whole-cell biocatalysts for alkane biohydroxylation.
  • Analysis of process engineering aspects for industrial scale-up.
  • Discussion of cofactor regeneration and product removal strategies.

Main Results:

  • Enzymatic and whole-cell systems show promise for selective alkane hydroxylation.
  • Integration with cofactor regeneration and product removal is crucial for efficient bioconversion.
  • Bioreactor design and operation are key for large-scale implementation.

Conclusions:

  • Alkane biohydroxylation offers a sustainable route to valuable alcohol products.
  • Further development of biocatalysts and bioprocesses is needed for industrial viability.
  • This technology has the potential to transform fine chemical synthesis from renewable feedstocks.