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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.
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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.
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Hydroboration-Oxidation of Alkenes03:08

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

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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...
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
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Stable BF2 Boracycles as Versatile Reagents for Selective Ortho C-H Functionalization.

Ganesh H Shinde1, Jonatan Babiker1, Michelle Mebrahtu1

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg, Gothenburg, Sweden, SE-41296.

Angewandte Chemie (International Ed. in English)
|January 17, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed a scalable, metal-free method for stable BF2 boracycles, valuable in organic synthesis. These boron compounds enable diverse functionalization and cross-coupling reactions for complex molecule construction.

Keywords:
BBr3BoronCross‐couplingLate‐stage functionalizationRadioiodination

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Area of Science:

  • Organoboron Chemistry
  • Synthetic Organic Chemistry

Background:

  • Boron reagents are vital for modern organic synthesis, especially in C-H functionalization and cross-coupling.
  • Developing stable and reactive boron species is key for efficient synthetic strategies.

Purpose of the Study:

  • To establish a metal-free, scalable protocol for synthesizing stable BF2 boracycles.
  • To demonstrate the utility of these BF2 boracycles as versatile intermediates in organic synthesis.

Main Methods:

  • Developed a robust, chromatography-free, multigram synthesis of BF2 boracycles.
  • Investigated the reactivity of BF2 boracycles in ipso-substitution reactions.
  • Evaluated their performance in Suzuki-Miyaura cross-coupling reactions.

Main Results:

  • Achieved a practical and efficient route to stable BF2 boracycles.
  • Demonstrated successful ipso-substitution yielding halogenated, hydroxylated, and azidated derivatives.
  • Showcased excellent reactivity in Suzuki-Miyaura couplings for C(sp2)-C(sp2) and C(sp2)-C(sp3) bond formation.

Conclusions:

  • BF2 boracycles are stable, reactive intermediates for late-stage diversification.
  • This method offers a streamlined approach to organoboron compounds for pharmaceutical synthesis and complex molecule construction.
  • Represents a significant advancement in organoboron chemistry with broad applicability.