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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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.
9.3K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.9K
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.
10.9K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.5K
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.
20.5K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
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,...
2.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.2K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Related Experiment Video

Updated: Jan 3, 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 directed sp2-C-H borylation.

Jiahang Lv1,2, Xiangyang Chen3, Xiao-Song Xue3,4

  • 1State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.

Nature
|November 15, 2019
PubMed
Summary

This study introduces a novel metal-free method for C-H borylation of arenes and heteroarenes using boron tribromide (BBr3). This approach efficiently synthesizes functionalized organoboron compounds, valuable for drug discovery and materials science.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Organoboron reagents are crucial building blocks in synthesizing natural products, pharmaceuticals, and organic materials.
  • Developing efficient, mild, and metal-free methods for organoboron synthesis is essential for expanding synthetic routes.

Purpose of the Study:

  • To present a general and metal-free method for the directed C-H borylation of arenes and heteroarenes.
  • To demonstrate the compatibility of this method with a wide array of functional groups.

Main Methods:

  • Directed C-H borylation of arenes and heteroarenes without metal catalysts.
  • Utilizing boron tribromide (BBr3) as both a reagent and catalyst.
  • Density functional theory (DFT) calculations to elucidate the reaction mechanism.

Main Results:

  • Successful synthesis of C7- and C4-borylated indoles under mild conditions.
  • Demonstrated broad functional group tolerance.
  • Established a reaction mechanism involving BBr3 acting as both reagent and catalyst.

Conclusions:

  • The developed metal-free C-H borylation offers a mild and efficient route to valuable organoboron intermediates.
  • The synthesized boron species can be readily transformed into natural products and drug scaffolds, highlighting the method's utility.