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Updated: Jul 4, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
09:45

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

水中の未活性化アルキルハリドを用いたバービエ・グリニャール型カルボニルアルキル化

Charlene C K Keh1, Chunmei Wei, Chao-Jun Li

  • 1Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA.

Journal of the American Chemical Society
|April 3, 2003
PubMed
まとめ

新しいBarbier-Grignard型水中反応により,水中の亜鉛,銅ヨウ酸化物,インジウム (I) クロリドの触媒を用いてアルキルハリドをアルデヒドに添加することができる. この方法は,原発,二次,三次アルキルハリドを芳香アルデヒドと効率的に結合します.

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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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Alcohols from Carbonyl Compounds: Grignard Reaction

Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the carbonyl carbon is a...
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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The carbonyl center is activated by...
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Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
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Esters to Alcohols: Grignard Reaction

The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the case of formate esters, secondary alcohols are formed.
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Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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