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Updated: May 23, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Grignard Method for Preparing Thioesters from Esters and Its Application to One-Pot Synthesis of Ketones and

Shaheen K Mulani1, Jiaao Kang1, Runlin Yang1

  • 1Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.

ACS Omega
|March 10, 2025
PubMed

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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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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
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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.
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