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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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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 halogen to form a...
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Acid Halides to Alcohols: LiAlH4 Reduction01:19

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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An aldehyde-stabilised alkoxyaluminium dication.

Annabel Benny1, Devika Vijayan1, Rajeshkumar Thayalan2

  • 1School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Vithura, Thiruvananthapuram 695551, India. venugopal@iisertvm.ac.in.

Chemical Communications (Cambridge, England)
|September 17, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel aluminum dication stabilized by aldehyde ligands. This compound, upon reaction with silane, releases the aldehydes, revealing a reactive aluminum center that catalyzes alkene hydrosilylation.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Aluminum compounds exhibit diverse Lewis acidity and reactivity.
  • Perfluoroalkyl groups significantly alter electronic and steric properties of metal complexes.
  • Aldehyde ligands can coordinate to metal centers, influencing reactivity.

Purpose of the Study:

  • To synthesize and characterize a novel perfluoro-tert-butoxyaluminum dication stabilized by aldehyde ligands.
  • To investigate the Lewis acidic reactivity of the synthesized dication.
  • To explore the potential of the aluminum center in catalytic transformations.

Main Methods:

  • Synthesis of the perfluoro-tert-butoxyaluminum dication using specific precursors.
  • Structural characterization using spectroscopic and crystallographic techniques.
  • Reactivity studies involving treatment with triethylsilane and subsequent catalytic testing.

Main Results:

  • Successful synthesis and structural elucidation of the [{(F3C)3CO}Al{4-MePhCHO}5]2+ dication.
  • Demonstration of deoxygenative elimination of aldehyde ligands upon reaction with Et3SiH.
  • Instantaneous promotion of alkene hydrosilylation by the unveiled reactive aluminum center.

Conclusions:

  • The perfluoro-tert-butoxyaluminum dication represents a unique Lewis acidic species.
  • The coordinated aldehydes serve as protecting groups, enabling the isolation of a reactive aluminum intermediate.
  • This system offers a novel pathway for generating active aluminum catalysts for hydrosilylation.