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Related Concept Videos

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

7.8K
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...
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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.
19.8K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.1K
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.
10.1K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
6.9K
Halogenation of Alkenes02:46

Halogenation of Alkenes

17.1K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
17.1K

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Related Experiment Video

Updated: May 2, 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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Cobalt-catalyzed C-H borylation.

Jennifer V Obligacion1, Scott P Semproni, Paul J Chirik

  • 1Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society
|March 5, 2014
PubMed
Summary

New cobalt catalysts efficiently perform C-H borylation of heterocycles and arenes under mild conditions. These catalysts show high activity, even at low loadings, with no need for excess borane reagents.

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Catalytic C-H borylation is crucial for functionalizing organic molecules.
  • Developing efficient and mild catalytic systems remains a key challenge.

Purpose of the Study:

  • To synthesize and evaluate novel pincer-ligated cobalt complexes for C-H borylation.
  • To investigate the catalytic activity and reaction conditions for borylation of heterocycles and arenes.

Main Methods:

  • Synthesis of pincer-ligated cobalt complexes.
  • Catalytic testing for C-H borylation reactions.
  • Optimization of reaction conditions (temperature, catalyst loading, reagents).

Main Results:

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  • The synthesized cobalt complexes exhibit high catalytic activity for C-H borylation.
  • Reactions proceed under mild conditions without requiring excess borane reagents.
  • High turnover numbers (up to 5000) were achieved for methyl furan-2-carboxylate at ambient temperature with low catalyst loadings (0.02 mol %).

    • Conclusions:

    • Pincer-ligated cobalt complexes are effective catalysts for C-H borylation.
    • The catalytic system offers a mild, efficient, and low-loading approach to borylation.
    • A catalytic cycle involving a cobalt(I)-(III) redox couple is proposed to explain the observed reactivity.