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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...

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Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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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,...

Radical Substitution: Allylic Bromination

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Updated: Jan 10, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Published on: February 24, 2015

Homoleptic Bismuth Alkynes: Isolable Reagents for Selective Alkynyl Radical Transfer.

Gargi Kundu^1,2, Felix Debbeler^1,2, Sascha Reith^1,2

¹Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Str. 4, 35032, Marburg, Germany.

Angewandte Chemie (International Ed. in English)

|November 24, 2025

Summary

Researchers developed new bismuth alkyne compounds for generating alkynyl radicals under mild, wet-chemical conditions. These compounds offer a transition-metal-free, non-toxic alternative for various synthetic applications.

Keywords:

Alkynyl radical Bismuth alkynes C–C coupling Radical borylation Thermal activation

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Published on: May 21, 2019

Area of Science:

Synthetic Organic Chemistry
Organometallic Chemistry
Radical Chemistry

Background:

Alkynyl radicals are valuable synthetic intermediates but difficult to access under standard wet-chemical conditions.
Bismuth compounds show potential for controlled radical reactions, attracting research interest.
Existing methods for alkynyl radical generation often involve harsh conditions or toxic reagents.

Purpose of the Study:

To synthesize and characterize novel homoleptic bismuth alkyne compounds.
To demonstrate the controlled release of alkynyl radicals from these bismuth compounds.
To explore the utility of these compounds in various C-C and C-heteroatom bond-forming reactions.

Main Methods:

Synthesis of homoleptic bismuth alkyne compounds, Bi(C≡CR)₃.
Electron Paramagnetic Resonance (EPR) spectroscopy to confirm radical generation.
Application of the compounds in Glaser-type homocoupling and C-C, C-B, C-Se, C-Te bond formation.

Main Results:

Successfully synthesized and characterized isolable bismuth alkyne compounds.
Demonstrated selective and facile release of alkynyl radicals, confirmed by EPR.
Utilized the generated alkynyl radicals in diverse coupling reactions, including those typically requiring polar pathways.

Conclusions:

Bismuth alkyne compounds provide a novel, efficient route for generating alkynyl radicals under mild, wet-chemical conditions.
These compounds serve as a transition-metal-free, non-toxic alternative to existing radical generation methods.
The developed methodology expands the scope of alkynyl radical chemistry in synthesis.